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Current Organic Chemistry

Author(s): N. Umadevi, G. Kumar, N.C. Gangi Reddy* and B.V. Subba Reddy*

DOI: 10.2174/1385272824999201210180732

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Recent Advances in C–H Activation and Functionalization of Quinazolinones/ Quinazolines

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Abstract

This review summarizes the transition metal-catalyzed direct C–H functionalization of quinazolinones and quinazolines through C-C, C-N and C-O bond formations. It focuses mainly on the C-H (sp2 or sp3) bond arylation, amination, sulfamidation, acetoxylation, halogenation, annulation of quinazolinones and quinazolines. This review illustrates the scope of C-H activation and functionalization of various quinazolinone and quinazoline derivatives.

Keywords: Quinazolinones, quinazolines, arylation, amination, sulfamidation, acetoxylation, halogenation, C-H activation, insertion, metallocycles, transition metals, oxidative coupling, reductive elimination, regioselective, chemoselective, cross-couplings.

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[1]
Wan, J.P.; Gan, L.; Liu, Y. Transition metal-catalyzed C-H bond functionalization in multicomponent reactions: a tool toward molecular diversity. Org. Biomol. Chem., 2017, 15(43), 9031-9043.
[http://dx.doi.org/10.1039/C7OB02011B] [PMID: 29075706]
[2]
Han, X.L.; Lin, P.P.; Li, Q. Recent advances of allenes in the first-row transition metals catalyzed CH activation reactions. Chin. Chem. Lett., 2019, 30, 1495-1502.
[http://dx.doi.org/10.1016/j.cclet.2019.04.027]
[3]
A review on C-H functionalization of “chromones and flavones” by Tian, S.; Luo, T.; Zhu, Y.; Wan. J.P. Chin. Chem. Lett., 2020, 2020, 1.
[http://dx.doi.org/10.1016/j.cclet.2020.07.042]
[4]
Strekalova, S.; Khrizanforov, M.; Sinyashin, O.; Budnikova, Y. Catalytic phosphorylation of aromatic C-H bonds: from traditional approaches to electrochemistry. Curr. Org. Chem., 2019, 23, 1756-1770.
[http://dx.doi.org/10.2174/1385272822666191007145336]
[5]
Pati, B.; Banerjee, S. Quinazolines: an illustrated review. J. Adv. Pharm. Educ. Res., 2013, 3, 136-151.
[6]
Srivastava, S.; Srivastava, S. Biological activity of quinazoline: a review. Int. J. Pharm. Sci. Res., 2015, 6, 1206-1213.
[7]
Michael, J.P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep., 2000, 17(6), 603-620.
[http://dx.doi.org/10.1039/a904850b] [PMID: 11152423]
[8]
Liu, J.F.; Kaselj, M.; Isome, Y.; Ye, P.; Sargent, K.; Sprague, K.; Cherrak, D.; Wilson, C.J.; Si, Y.; Yohannes, D.; Ng, S.C. Design and synthesis of a quinazolinone natural product-templated library with cytotoxic activity. J. Comb. Chem., 2006, 8(1), 7-10.
[http://dx.doi.org/10.1021/cc050108g] [PMID: 16398546]
[9]
Asif, M. Chemical characteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives. Int. J. Med. Chem., 2014, 2014, 1-27.
[10]
Liverton, N.J.; Armstrong, D.J.; Claremon, D.A.; Remy, D.C.; Baldwin, J.J.; Lynch, R.J.; Zhang, G.; Gould, R.J. Nonpeptide glycoprotein IIb/IIIa inhibitors: substituted quinazolinediones and quinazolinones as potent fibrinogen receptor antagonists. Bioorg. Med. Chem. Lett., 1998, 8(5), 483-486.
[http://dx.doi.org/10.1016/S0960-894X(98)00047-X] [PMID: 9871603]
[11]
Hirai, S.; Kikuchi, H.; Kim, H.S.; Begum, K.; Wataya, Y.; Tasaka, H.; Miyazawa, Y.; Yamamoto, K.; Oshima, Y. Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite. J. Med. Chem., 2003, 46(20), 4351-4359.
[http://dx.doi.org/10.1021/jm0302086] [PMID: 13678413]
[12]
Zhu, S.; Meng, L.; Zhang, Q.; Wei, L. Synthesis and evaluation of febrifugine analogues as potential antimalarial agents. Bioorg. Med. Chem. Lett., 2006, 16(7), 1854-1858.
[http://dx.doi.org/10.1016/j.bmcl.2006.01.009] [PMID: 16434194]
[13]
Hour, M.J.; Tsai, S.C.; Wu, H.C.; Lin, M.W.; Chung, J.G.; Wu, J.B.; Chiang, J.H.; Tsuzuki, M.; Yang, J.S. Antitumor effects of the novel quinazolinone MJ-33: inhibition of metastasis through the MAPK, AKT, NF-κB and AP-1 signaling pathways in DU145 human prostate cancer cells. Int. J. Oncol., 2012, 41(4), 1513-1519.
[http://dx.doi.org/10.3892/ijo.2012.1560] [PMID: 22825655]
[14]
Hour, M.J.; Lee, K.T.; Wu, Y.C.; Wu, C.Y.; You, B.J.; Chen, T.L.; Lee, H.Z. A novel antitubulin agent, DPQZ, induces cell apoptosis in human oral cancer cells through Ras/Raf inhibition and MAP kinases activation. Arch. Toxicol., 2013, 87(5), 835-846.
[http://dx.doi.org/10.1007/s00204-012-0991-3] [PMID: 23212307]
[15]
Malamas, M.S.; Millen, J. Quinazolineacetic acids and related analogues as aldose reductase inhibitors. J. Med. Chem., 1991, 34(4), 1492-1503.
[http://dx.doi.org/10.1021/jm00108a038] [PMID: 1901912]
[16]
Chan, J.H.; Hong, J.S.; Kuyper, L.F.; Baccanari, D.P.; Joyner, S.S.; Tansik, R.L.; Boytos, C.M.; Rudolph, S.K. Selective inhibitors of Candida albicans dihydrofolate reductase: activity and selectivity of 5-(arylthio)-2,4-diaminoquinazolines. J. Med. Chem., 1995, 38(18), 3608-3616.
[http://dx.doi.org/10.1021/jm00018a021] [PMID: 7658448]
[17]
Kunes, J.; Bazant, J.; Pour, M.; Waisser, K.; Slosárek, M.; Janota, J. Quinazoline derivatives with antitubercular activity. Farmaco, 2000, 55(11-12), 725-729.
[http://dx.doi.org/10.1016/S0014-827X(00)00100-2] [PMID: 11204949]
[18]
Waisser, K.; Gregor, J.; Dostál, H.; Kunes, J.; Kubicová, L.; Klimesová, V.; Kaustová, J. Influence of the replacement of the oxo function with the thioxo group on the antimycobacterial activity of 3-aryl-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-diones and 3-arylquinazoline-2,4(1H,3H)-diones. Farmaco, 2001, 56(10), 803-807.
[http://dx.doi.org/10.1016/S0014-827X(01)01134-X] [PMID: 11718275]
[19]
Vostrova, L.N.; Voronina, T.A.; Karaseva, T.L.; Gernega, S.A.; Ivanov, E.I.; Kirichenka, A.M.; Yu, M. Synthesis and anticonvulsant activity of benzimidazo[1, 2-c]quinazolines. Pharm. Chem. J., 1986, 20, 404-406.
[http://dx.doi.org/10.1007/BF00758335]
[20]
Majhi, B.; Kundu, D.; Ghosh, T.; Ranu, B.C. Retracted: palladium-catalyzed decarboxylative selective acylation of 4H-benzo[d][1,3]oxazin-4-one derivatives with α-oxo carboxylic acids via preferential cyclic imine-N-directed aryl C−H activation. Adv. Synth. Catal., 2016, 358, 283-295.
[http://dx.doi.org/10.1002/adsc.201500786]
[21]
Verbitskly, E.V.; Rusinov, G.L.; Chupakhln, O.N.; Charushin, V.N. Recent advances in direct C–H functionalization of pyrimidines. Synthesis, 2018, 50, 193-210.
[http://dx.doi.org/10.1055/s-0036-1589520]
[22]
Connolly, D.J.; Cusack, D.; Sullivan, T.P.O.; Guiry, P.J. Synthesis of quinazolinones and quinazolines. Tetrahedron, 2005, 61, 10153-10202.
[http://dx.doi.org/10.1016/j.tet.2005.07.010]
[23]
Hameed, A.; Al-Rashida, M.; Uroos, M.; Ali, S.A. Arshia; Ishtiaq, M.; Khan, K.M. Quinazoline and quinazolinone as important medicinal scaffolds: a comparative patent review (2011-2016). Expert Opin. Ther. Pat., 2018, 28(4), 281-297.
[http://dx.doi.org/10.1080/13543776.2018.1432596] [PMID: 29368977]
[24]
Garad, D.N.; Viveki, A.B.; Mhaske, S.B. Pd-Catalyzed regioselective mono-arylation: quinazolinone as the inherent directing group for C(sp2)-H activation. J. Org. Chem., 2017, 82(12), 6366-6372.
[http://dx.doi.org/10.1021/acs.joc.7b00948] [PMID: 28523916]
[25]
Deprez, N.R.; Sanford, M.S. Synthetic and mechanistic studies of Pd-catalyzed C-H arylation with diaryliodonium salts: evidence for a bimetallic high oxidation state Pd intermediate. J. Am. Chem. Soc., 2009, 131(31), 11234-11241.
[http://dx.doi.org/10.1021/ja904116k] [PMID: 19621899]
[26]
Topczewski, J.J.; Sanford, M.S. Carbon-hydrogen (C-H) bond activation at PdIV: a Frontier in C-H functionalization cataly. Chem. Sci. (Camb.), 2015, 6(1), 70-76.
[http://dx.doi.org/10.1039/C4SC02591A] [PMID: 25544882]
[27]
Alawode, O.E.; Naganaboina, V.K.; Liyanage, T.; Desper, J.; Rayat, S. One-pot cascade approach to phenanthridine-fused quinazoliniminiums from heteroenyne-allenes. Org. Lett., 2014, 16(5), 1494-1497.
[http://dx.doi.org/10.1021/ol500314x] [PMID: 24547771]
[28]
Gupta, P.K.; Yadav, N.; Jaiswal, S.; Asad, M.; Kant, R.; Hajela, K. Palladium-catalyzed synthesis of phenanthridine/benzoxazine-fused quinazolinones by intramolecular C-H bond activation. Chemistry, 2015, 21(38), 13210-13215.
[http://dx.doi.org/10.1002/chem.201501591] [PMID: 26230355]
[29]
Lee, J.B.; Kang, M.E.; Kim, J.; Lee, C.Y.; Kee, J.M.; Myung, K.; Park, J.U.; Hong, S.Y. Direct diversification of unmasked quinazolin-4(3H)-ones through orthogonal reactivity modulation. Chem. Commun. (Camb.), 2017, 53(75), 10394-10397.
[http://dx.doi.org/10.1039/C7CC05794F] [PMID: 28876024]
[30]
Karthikeyan, J.; Cheng, C.H. Synthesis of phenanthridinones from N-methoxybenzamides and arenes by multiple palladium-catalyzed C-H activation steps at room temperature. Angew. Chem. Int. Ed. Engl., 2011, 50(42), 9880-9883.
[http://dx.doi.org/10.1002/anie.201104311] [PMID: 21887827]
[31]
Wang, G.W.; Yuan, T.T.; Li, D.D. One-pot formation of C-C and C-N bonds through palladium-catalyzed dual C-H activation: synthesis of phenanthridinones. Angew. Chem. Int. Ed. Engl., 2011, 50(6), 1380-1383.
[http://dx.doi.org/10.1002/anie.201005874] [PMID: 21290517]
[32]
Laclef, S.; Harari, M.; Godeau, J.; Schmitz-Afonso, I.; Bischoff, L.; Hoarau, C.; Levacher, V.; Fruit, C.; Besson, T. Ligand-free Pd-catalyzed and copper-assisted C-H arylation of quinazolin-4-ones with aryl iodides under microwave heating. Org. Lett., 2015, 17(7), 1700-1703.
[http://dx.doi.org/10.1021/acs.orglett.5b00467] [PMID: 25781369]
[33]
Storr, T.E.; Baumann, C.G.; Thatcher, R.J.; De Ornellas, S.; Whitwood, A.C.; Fairlamb, I.J.S. Pd(0)/Cu(I)-mediated direct arylation of 2′-deoxyadenosines: mechanistic role of Cu(I) and reactivity comparisons with related purine nucleosides. J. Org. Chem., 2009, 74(16), 5810-5821.
[http://dx.doi.org/10.1021/jo9012282] [PMID: 19630437]
[34]
Huang, J.; Chan, J.; Chen, Y.; Borths, C.J.; Baucom, K.D.; Larsen, R.D.; Faul, M.M. A highly efficient palladium/copper cocatalytic system for direct arylation of heteroarenes: an unexpected effect of Cu(Xantphos)I. J. Am. Chem. Soc., 2010, 132(11), 3674-3675.
[http://dx.doi.org/10.1021/ja100354j] [PMID: 20180566]
[35]
Lesieur, M.; Lazreg, F.; Cazin, C.S. A cooperative Pd-Cu system for direct C-H bond arylation. Chem. Commun. (Camb.), 2014, 50(64), 8927-8929.
[http://dx.doi.org/10.1039/C4CC03201B] [PMID: 24976025]
[36]
Gorelsky, S.I. Tuning the regioselectivity of palladium-catalyzed direct arylation of azoles by metal coordination. Organometallics, 2012, 31, 794-797.
[http://dx.doi.org/10.1021/om2012612]
[37]
Godeau, J.; Harari, M.; Laclef, S.; Deau, E.; Fruit, C.; Besson, T. Cu/Pd-Catalyzed C-2–H arylation of quinazolin-4 (3H)-ones with (hetero) aryl halides. Eur. J. Org. Chem., 2015, 35, 7705-7717.
[http://dx.doi.org/10.1002/ejoc.201501129]
[38]
René, O.; Fagnou, K. Evaluation of electron-deficient phosphine ligands for direct arylation of heterocycles. Adv. Synth. Catal., 2010, 352, 2116-2120.
[http://dx.doi.org/10.1002/adsc.201000397]
[39]
Huang, C.; Gevorgyan, V. Synthesis of unsymmetrical o-biphenols and o-binaphthols via silicon-tethered Pd-catalyzed C-H arylation. Org. Lett., 2010, 12(10), 2442-2445.
[http://dx.doi.org/10.1021/ol100924n] [PMID: 20423110]
[40]
Lafrance, M.; Lapointe, D.; Fagnou, K. Mild and efficient palladium-catalyzed intramolecular direct arylation reactions. Tetrahedron, 2008, 64, 6015-6020.
[http://dx.doi.org/10.1016/j.tet.2008.01.057]
[41]
Hitce, J.; Retailleau, P.; Baudoin, O. Palladium-catalyzed intramolecular C(sp3)-H functionalization: catalyst development and synthetic applications. Chemistry, 2007, 13(3), 792-799.
[http://dx.doi.org/10.1002/chem.200600811] [PMID: 17044108]
[42]
Loidreau, Y.; Besson, T. Microwave-assisted thermal decomposition of formamide: a tool for coupling a pyrimidine ring with an aromatic partner. Tetrahedron, 2011, 67, 4852-4857.
[http://dx.doi.org/10.1016/j.tet.2011.05.010]
[43]
Nouira, I.; Kostakis, I.K.; Dubouilh, C.; Chosson, E.; Iannelli, M.; Besson, T. Decomposition of formamide assisted by microwaves, a tool for synthesis of nitrogen-containing heterocycles. Tetrahedron Lett., 2008, 49, 7033-7036.
[http://dx.doi.org/10.1016/j.tetlet.2008.09.135]
[44]
Kostakis, I.K.; Elomri, A.; Seguin, E.; Iannelli, M.; Besson, T. Rapid synthesis of 2, 3-disubstituted-quinazolin-4-ones enhanced by microwave-assisted decomposition of formamide. Tetrahedron Lett., 2007, 48, 6609-6613.
[http://dx.doi.org/10.1016/j.tetlet.2007.07.114]
[45]
Carlström, A.S.; Torbjön, S. Aspects of the palladium-catalyzed coupling between aryl halides and 2-amidoacrylates. Acta Chem. Scand., 1992, 46, 163-171.
[http://dx.doi.org/10.3891/acta.chem.scand.46-0163]
[46]
Xue, L.; Lin, Z. Theoretical aspects of palladium-catalysed carbon-carbon cross-coupling reactions. Chem. Soc. Rev., 2010, 39(5), 1692-1705.
[http://dx.doi.org/10.1039/B814973A] [PMID: 20419215]
[47]
Harari, M.; Couly, F.; Fruit, C.; Besson, T. Pd-Catalyzed and copper assisted regioselective sequential C2 and C7 arylation of thiazolo[5,4-f]quinazolin-9(8H)-one with aryl halides. Org. Lett., 2016, 18(13), 3282-3285.
[http://dx.doi.org/10.1021/acs.orglett.6b01552] [PMID: 27314437]
[48]
Grosse, S.; Pillard, C.; Massip, S.; Marchivie, M.; Jarry, C.; Bernard, P.; Guillaumet, G. Ligandless palladium-catalyzed regioselective direct C-H arylation of imidazo[1,2-a]imidazole derivatives. J. Org. Chem., 2015, 80(17), 8539-8551.
[http://dx.doi.org/10.1021/acs.joc.5b00534] [PMID: 26243437]
[49]
Pitts, A.K.; Hara, F.O.; Snell, R.H.; Gaunt, M.J. A concise and scalable strategy for the total synthesis of dictyodendrin B based on sequential C- H functionalization.Angew. Chem. Int., Ed.,, 2015, 54, pp. 5451-5455.
[http://dx.doi.org/10.1002/anie.201500067]
[50]
Xu, X.; Zhao, L.; Li, Y.; Soulé, J.F.; Doucet, H. Intermolecular versus intramolecular palladium-catalyzed direct arylations between 1-(2-bromobenzyl)imidazoles and aryl bromides. Adv. Synth. Catal., 2015, 357, 2869-2882.
[http://dx.doi.org/10.1002/adsc.201500332]
[51]
Fuse, S.; Morita, T.; Johmoto, K.; Uekusa, H.; Tanaka, H. Directing/protecting-group-free synthesis of tetraaryl-substituted pyrazoles through four direct arylations on an unsubstituted pyrazole scaffold. Chemistry, 2015, 21(41), 14370-14375.
[http://dx.doi.org/10.1002/chem.201502399] [PMID: 26330168]
[52]
Bedford, R.B.; Durrant, S.J.; Montgomery, M. Catalyst-switchable regiocontrol in the direct arylation of remote C-H groups in pyrazolo[1,5-a]pyrimidines. Angew. Chem. Int. Ed. Engl., 2015, 54(30), 8787-8790.
[http://dx.doi.org/10.1002/anie.201502150] [PMID: 26095315]
[53]
Tani, S.; Uehara, T.N.; Yamaguchi, J.; Itami, K. Programmed synthesis of arylthiazoles through sequential C–H couplings. Chem. Sci. (Camb.), 2014, 5, 123-135.
[http://dx.doi.org/10.1039/C3SC52199K]
[54]
Johnson, B.M.; Huestis, M.P. Sequential C3 and C5 direct C–H arylation of imidazo[1,2-a]pyrazines with (hetero)aryl bromides. Eur. J. Org. Chem., 2014, 2014, 1589-1593.
[http://dx.doi.org/10.1002/ejoc.201301802]
[55]
Iaroshenko, V.O.; Gevorgyan, A.; Davydova, O.; Villinger, A.; Langer, P. Regioselective and guided C-H activation of 4-nitropyrazoles. J. Org. Chem., 2014, 79(7), 2906-2915.
[http://dx.doi.org/10.1021/jo4025418] [PMID: 24601649]
[56]
Bellina, F.; Lessi, M.; Manzini, C. Mild palladium-catalyzed regioselective direct arylation of azoles promoted by tetrabutylammonium acetate. Eur. J. Org. Chem., 2013, 2013, 5621-5630.
[http://dx.doi.org/10.1002/ejoc.201300704]
[57]
Couly, F.; Benard, C.D.; Besson, T.; Fruit, C.; Late-Stage, C.H. Arylation of thiazolo [5, 4-f] quinazolin-9 (8H)-one backbone: synthesis of an array of potential kinase inhibitors. Synthesis, 2017, 49, 4615-4622.
[http://dx.doi.org/10.1055/s-0036-1588434]
[58]
Yang, W.; Chen, J.; Huang, X.; Ding, J.; Liu, M.; Wu, H. Pd-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)-quinazolinones: synthesis of fluorescent indazolo[3,2-b]quinazolinones. Org. Lett., 2014, 16(20), 5418-5421.
[http://dx.doi.org/10.1021/ol5026553] [PMID: 25290066]
[59]
Butschke, B.; Schwarz, H. Mechanistic Study on the Gas-Phase Generation of “Rollover”-Cyclometalated [M(bipy − H)]+ (M = Ni, Pd, Pt). Chem. Sci. (Camb.), 2010, 29, 6002-6011.
[60]
Yang, W.; Qiao, R.; Chen, J.; Huang, X.; Liu, M.; Gao, W.; Ding, J.; Wu, H. Palladium-catalyzed Cascade reaction of 2-amino-N'-arylbenzohydrazides with triethyl orthobenzoates to construct indazolo[3,2-b]quinazolinones. J. Org. Chem., 2015, 80(1), 482-489.
[http://dx.doi.org/10.1021/jo5024848] [PMID: 25437529]
[61]
Tsang, W.C.P.; Zheng, N.; Buchwald, S.L.J.; Combined, C. Combined C-H functionalization/C-N bond formation route to carbazoles. J. Am. Chem. Soc., 2005, 127(42), 14560-14561.
[http://dx.doi.org/10.1021/ja055353i] [PMID: 16231894]
[62]
Shibata, T.; Takayasu, S.; Yuzawa, S.; Otani, T. Rh(III)-catalyzed C-H bond activation along with “rollover” for the synthesis of 4-azafluorenes. Org. Lett., 2012, 14(19), 5106-5109.
[http://dx.doi.org/10.1021/ol302375c] [PMID: 22985424]
[63]
Tsang, W.C.P.; Munday, R.H.; Brasche, G.; Zheng, N.; Buchwald, S.L.J. Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation. J. Org. Chem., 2008, 73(19), 7603-7610.
[http://dx.doi.org/10.1021/jo801273q] [PMID: 18761437]
[64]
Jordan-Hore, J.A.; Johansson, C.C.C.; Beck, E.M.; Gaunt, M.J.; Gaunt, M.J.J. Oxidative Pd(II)-catalyzed C-H bond amination to carbazole at ambient temperature. J. Am. Chem. Soc., 2008, 130(48), 16184-16186.
[http://dx.doi.org/10.1021/ja806543s] [PMID: 18998652]
[65]
Butschke, B.; Schwarz, H. “Rollover” cyclometalation–early history, recent developments, mechanistic insights and application aspects. Chem. Sci. (Camb.), 2012, 3, 308-326.
[http://dx.doi.org/10.1039/C1SC00651G]
[66]
Banerjee, A.; Subramanian, P.; Kaliappan, K.P. Copper-catalyzed Cascade amination route to N-aryl benzimidazoquinazolinones. J. Org. Chem., 2016, 81(21), 10424-10432.
[http://dx.doi.org/10.1021/acs.joc.6b01287] [PMID: 27518379]
[67]
Vemula, S.R.; Kumar, D.; Cook, G.R. Palladium-catalyzed allylic amidation with N-heterocycles via sp3 C–H oxidation. ACS Catal., 2016, 6, 5295-5301.
[http://dx.doi.org/10.1021/acscatal.6b01818]
[68]
Feng, Y.; Li, Y.; Yu, Y.; Wang, L.; Cui, X. Iridium-catalysed direct sulfamidation of quinazolinones. RSC Adv, 2018, 8, 8450-8454.
[http://dx.doi.org/10.1039/C8RA00524A]
[69]
Kim, J.; Chang, S. Iridium-catalyzed direct C-H amidation with weakly coordinating carbonyl directing groups under mild conditions. Angew. Chem. Int. Ed. Engl., 2014, 53(8), 2203-2207.
[http://dx.doi.org/10.1002/anie.201310544] [PMID: 24470125]
[70]
Kim, J.; Kim, J.; Chang, S. Ruthenium-catalyzed direct C-H amidation of arenes including weakly coordinating aromatic ketones. Chemistry, 2013, 19(23), 7328-7333.
[http://dx.doi.org/10.1002/chem.201301025] [PMID: 23616285]
[71]
Reddy, B.V.S.; Narasimhulu, G.; Umadevi, N.; Yadav, J.S. Quinazolinone-directed C–H activation: a novel strategy for the acetoxylation–methoxylation of the arenes. Synlett, 2012, 23, 1364-1370.
[http://dx.doi.org/10.1055/s-0031-1290962]
[72]
Reddy, B.V.S.; Reddy, L.R.; Corey, E.J. Novel acetoxylation and C-C coupling reactions at unactivated positions in α-amino acid derivatives. Org. Lett., 2006, 8(15), 3391-3394.
[http://dx.doi.org/10.1021/ol061389j] [PMID: 16836413]
[73]
Reddy, B.V.S.; Ramesh, K.; Yadav, J.S. First example of quinoxaline-directed CH activation: a novel method for acetoxylation of arenes. Synlett, 2011, 15, 169-172.
[http://dx.doi.org/10.1055/s-0030-1259292]
[74]
Reddy, B.V.S.; Revathi, G.; Reddy, A.S.; Yadav, J.S. Palladium (II)-catalyzed auxiliary-directed CH activation for the regioselective ortho arylation of N-(2-benzoylphenyl) benzamides. Synlett, 2011, 16, 2374-2378.
[http://dx.doi.org/10.1055/s-0030-1260314]
[75]
Muehlhofer, M.; Strassner, T.; Herrmann, W.A. New catalyst systems for the catalytic conversion of methane into methanol. Angew. Chem. Int. Ed. Engl., 2002, 41(10), 1745-1747.
[http://dx.doi.org/10.1002/1521-3773(20020517)41:10<1745:AID-ANIE1745>3.0.CO;2-E] [PMID: 19750703]
[76]
Garad, D.N.; Mhaske, S.B. Diversification of quinazolinones by Pd-catalyzed C(sp3)-acetoxylation. J. Org. Chem., 2017, 82(19), 10470-10478.
[http://dx.doi.org/10.1021/acs.joc.7b01934] [PMID: 28845987]
[77]
Rouquet, G.; Chatani, N. Catalytic functionalization of C(sp2)-H and C(sp3)-H bonds by using bidentate directing groups. Angew. Chem. Int. Ed. Engl., 2013, 52(45), 11726-11743.
[http://dx.doi.org/10.1002/anie.201301451] [PMID: 24105797]
[78]
Dick, A.R.; Hull, K.L.; Sanford, M.S. A highly selective catalytic method for the oxidative functionalization of C-H bonds. J. Am. Chem. Soc., 2004, 126(8), 2300-2301.
[http://dx.doi.org/10.1021/ja031543m] [PMID: 14982422]
[79]
Dabiri, M.; Lehi, N.F.; Movahed, S.K.; Khavasi, H.R. Pd-Catalyzed regioselective C–H halogenation of quinazolinones and benzoxazinones. Org. Biomol. Chem., 2017, 15, 626-6268.
[http://dx.doi.org/10.1039/C7OB01534H]
[80]
Sun, X.; Sun, Y.; Zhang, C.; Rao, Y. Room-temperature Pd-catalyzed C-H chlorination by weak coordination: one-pot synthesis of 2-chlorophenols with excellent regioselectivity. Chem. Commun. (Camb.), 2014, 50(10), 1262-1264.
[http://dx.doi.org/10.1039/C3CC47431C] [PMID: 24336469]
[81]
Voskressensky, G.; Golantsov, N.E.; Maharramov, A.M. Recent advances in bromination of aromatic and heteroaromatic compounds. Synthesis, 2016, 48, 615-643.
[http://dx.doi.org/10.1055/s-0035-1561503]
[82]
Sun, M.; Chen, X.; Zhang, L.; Sun, W.; Wang, Z.; Guo, P.; Li, Y.M.; Yang, X.J. Efficient, versatile and practical palladium-catalyzed highly regioselective ortho-halogenation of azoxybenzenes. Org. Biomol. Chem., 2016, 14(1), 323-329.
[http://dx.doi.org/10.1039/C5OB02153G] [PMID: 26574708]
[83]
Powers, D.C.; Geibel, M.A.L.; Klein, J.E.M.N.; Ritter, T. Bimetallic palladium catalysis: direct observation of Pd(III)-Pd(III) intermediates. J. Am. Chem. Soc., 2009, 131(47), 17050-17051.
[http://dx.doi.org/10.1021/ja906935c] [PMID: 19899740]
[84]
Powers, D.C.; Ritter, T. Bimetallic Pd(III) complexes in palladium-catalysed carbon–heteroatom bond formation. Nat. Chem., 2009, 1(4), 302-309.
[http://dx.doi.org/10.1038/nchem.246] [PMID: 21500602]
[85]
Powers, D.C.; Ritter, T. Bimetallic redox synergy in oxidative palladium catalysis. Acc. Chem. Res., 2012, 45(6), 840-850.
[http://dx.doi.org/10.1021/ar2001974] [PMID: 22029861]
[86]
Lu, H.; Yang, Q.; Zhou, Y.; Guo, Y.; Deng, Z.; Ding, Q.; Peng, Y. Cross-coupling/annulations of quinazolones with alkynes for access to fused polycyclic heteroarenes under mild conditions. Org. Biomol. Chem., 2014, 12(5), 758-764.
[http://dx.doi.org/10.1039/C3OB41955J] [PMID: 24337052]
[87]
Feng, Y.; Tian, N.; Li, Y.; Jia, C.; Li, X.; Wang, L.; Cui, X. Construction of fused polyheterocycles through sequential [4 + 2] and [3 + 2] cycloadditions. Org. Lett., 2017, 19(7), 1658-1661.
[http://dx.doi.org/10.1021/acs.orglett.7b00452] [PMID: 28286958]
[88]
Phipps, R.J.; Grimster, N.P.; Gaunt, M.J. Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions. J. Am. Chem. Soc., 2008, 130(26), 8172-8174.
[http://dx.doi.org/10.1021/ja801767s] [PMID: 18543910]
[89]
Beck, E.M.; Grimster, N.P.; Hatley, R.; Gaunt, M.J. Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: regioselective and switchable C-H alkenylation and annulation of pyrroles. J. Am. Chem. Soc., 2006, 128(8), 2528-2529.
[http://dx.doi.org/10.1021/ja058141u] [PMID: 16492024]
[90]
Satoh, T.; Ogino, S.; Miura, M.; Nomura, M. Synthesis of highly substituted 1,3-butadienes by palladium-catalyzed arylation of internal alkynes. Angew. Chem. Int. Ed. Engl., 2004, 43(38), 5063-5065.
[http://dx.doi.org/10.1002/anie.200460409] [PMID: 15384119]
[91]
Zhang, C.; Xu, Z.; Zhang, L.; Jiao, N. Copper-catalyzed aerobic oxidative coupling of aryl acetaldehydes with anilines leading to α-ketoamides. Angew. Chem. Int. Ed. Engl., 2011, 50(47), 11088-11092.
[http://dx.doi.org/10.1002/anie.201105285] [PMID: 21919176]
[92]
Kumar, D.; Vemula, S.R.; Cook, G.R. Merging C–H bond functionalization with amide alcoholysis: en route to 2-aminopyridines. ACS Catal., 2016, 6, 3531-3536.
[http://dx.doi.org/10.1021/acscatal.6b00728]
[93]
Li, B.; Feng, H.; Wang, N.; Ma, J.; Song, H.; Xu, S.; Wang, B. Ruthenium-catalyzed oxidative coupling/cyclization of isoquinolones with alkynes through C-H/N-H activation: mechanism study and synthesis of dibenzo[a,g]quinolizin-8-one derivatives. Chemistry, 2012, 18(40), 12873-12879.
[http://dx.doi.org/10.1002/chem.201201862] [PMID: 22930580]
[94]
Dooley, J.D.; Reddy Chidipudi, S.; Lam, H.W. Catalyst-controlled divergent C-H functionalization of unsymmetrical 2-aryl cyclic 1,3-dicarbonyl compounds with alkynes and alkenes. J. Am. Chem. Soc., 2013, 135(29), 10829-10836.
[http://dx.doi.org/10.1021/ja404867k] [PMID: 23806064]
[95]
Nan, J.; Zuo, Z.; Luo, L.; Bai, L.; Zheng, H.; Yuan, Y.; Liu, J.; Luan, X.; Wang, Y. Ru(II)-catalyzed vinylative dearomatization of naphthols via a C(sp2)-H bond activation approach. J. Am. Chem. Soc., 2013, 135(46), 17306-17309.
[http://dx.doi.org/10.1021/ja410060e] [PMID: 24195654]
[96]
Wang, Y.; Zheng, Z.; Zhang, L. Ruthenium-catalyzed oxidative transformations of terminal alkynes to ketenes by using tethered sulfoxides: access to β-lactams and cyclobutanones. Angew. Chem. Int. Ed. Engl., 2014, 53(36), 9572-9576.
[http://dx.doi.org/10.1002/anie.201403796] [PMID: 25044723]
[97]
Li, B.; Park, Y.; Chang, S. Regiodivergent access to five- and six-membered benzo-fused lactams: Ru-catalyzed olefin hydrocarbamoylation. J. Am. Chem. Soc., 2014, 136(3), 1125-1131.
[http://dx.doi.org/10.1021/ja411913e] [PMID: 24410349]
[98]
Warratz, S.; Kornhaaß, C.; Cajaraville, A.; Niepötter, B.; Stalke, D.; Ackermann, L. Ruthenium(II)-catalyzed C-H activation/alkyne annulation by weak coordination with O2 as the sole oxidant. Angew. Chem. Int. Ed. Engl., 2015, 54(18), 5513-5517.
[http://dx.doi.org/10.1002/anie.201500600] [PMID: 25737001]
[99]
Manoharan, R.; Jeganmohan, M. Synthesis of isoindolinones via a ruthenium-catalyzed cyclization of N-substituted benzamides with allylic alcohols. Chem. Commun. (Camb.), 2015, 51(14), 2929-2932.
[http://dx.doi.org/10.1039/C4CC09877C] [PMID: 25587828]
[100]
Zheng, Y.; Song, W.B.; Zhang, S.W.; Xuan, L.J. Ruthenium-catalyzed oxidative coupling of 2-aryl-4-quinazolinones with olefins: synthesis of pyrrolo[2,1-b]quinazolin-9(1H)-one motifs. Org. Biomol. Chem., 2015, 13(23), 6474-6478.
[http://dx.doi.org/10.1039/C5OB00601E] [PMID: 25996242]
[101]
Ferrer Flegeau, E.; Bruneau, C.; Dixneuf, P.H.; Jutand, A. Autocatalysis for C-H bond activation by ruthenium(II) complexes in catalytic arylation of functional arenes. J. Am. Chem. Soc., 2011, 133(26), 10161-10170.
[http://dx.doi.org/10.1021/ja201462n] [PMID: 21604765]
[102]
Ackermann, L.; Vicente, R.; Potukuchi, H.K.; Pirovano, V. Mechanistic insight into direct arylations with ruthenium(II) carboxylate catalysts. Org. Lett., 2010, 12(21), 5032-5035.
[http://dx.doi.org/10.1021/ol102187e] [PMID: 20929268]
[103]
Jiang, X.; Yang, Q.; Yuan, J.; Deng, Z.; Mao, X.; Peng, Y.; Yu, C. Rhodium-catalyzed tandem C–H activation and aza-Michael addition of 2-arylquinazolin-4-ones with acrylates for the synthesis of pyrrolo[2,1-b]quinazolin-9(1H)-one derivatives. Tetrahedron, 2016, 72, 1238-1243.
[http://dx.doi.org/10.1016/j.tet.2016.01.020]
[104]
Song, G.; Wang, F.; Li, X.C-C. C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation. Chem. Soc. Rev., 2012, 41(9), 3651-3678.
[http://dx.doi.org/10.1039/c2cs15281a] [PMID: 22377832]
[105]
Tian, P.; Feng, C.; Loh, T.P. Rhodium-catalysed C(sp2)-C(sp2) bond formation via C-H/C-F activation. Nat. Commun., 2015, 6, 7472-7479.
[http://dx.doi.org/10.1038/ncomms8472] [PMID: 26081837]
[106]
Zhao, S.; Yu, R.; Chen, W.; Liu, M.; Wu, H. Efficient approach to mesoionic triazolo[5,1-a]isoquinolium through rhodium-catalyzed annulation of triazoles and internal alkynes. Org. Lett., 2015, 17(11), 2828-2831.
[http://dx.doi.org/10.1021/acs.orglett.5b01247] [PMID: 26008226]
[107]
Xia, Y.; Feng, S.; Liu, Z.; Zhang, Y.; Wang, J. Rhodium(I)-catalyzed sequential C(sp)-C(sp3) and C(sp3)-C(sp3) bond formation through migratory carbene insertion. Angew. Chem. Int. Ed. Engl., 2015, 54(27), 7891-7894.
[http://dx.doi.org/10.1002/anie.201503140] [PMID: 25982105]
[108]
Lou, M.; Deng, Z.; Mao, X.; Fu, Y.; Yang, Q.; Peng, Y. Rhodium-catalyzed C-H bond activation alkylation and cyclization of 2-arylquinazolin-4-ones. Org. Biomol. Chem., 2018, 16(11), 1851-1859.
[http://dx.doi.org/10.1039/C8OB00147B] [PMID: 29469147]
[109]
Mei, S.T.; Jiang, K.; Wang, N.J.; Shuai, L.; Yuan, Y.; Wei, Y. Rhodium-catalyzed direct C–H vinylation of arenes to access styrenes with vinyl acetate as a vinyl source. Eur. J. Org. Chem., 2015, 2015, 6135-6140.
[http://dx.doi.org/10.1002/ejoc.201500945]
[110]
Sk, M.R.; Maji, M.S. Cobalt(III)-catalyzed ketone-directed C–H vinylation using vinyl acetateOrg. Chem. Front., 2020, 7, 19-24.
[http://dx.doi.org/10.1039/C9QO01164A]
[111]
Peng, Y.; Zeng, M.; Wang, H.; Zhu, J.; Yang, Q.; Deng, Z.; Yu, C. Quinazoline-directed regioselective arylation via palladium catalysis: synthesis of 2-(1-biaryl)-4-arylquinazolines. Tetrahedron, 2015, 71, 9457-9462.
[http://dx.doi.org/10.1016/j.tet.2015.10.042]
[112]
Kalyani, D.; McMurtrey, K.B.; Neufeldt, S.R.; Sanford, M.S. Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis. J. Am. Chem. Soc., 2011, 133(46), 18566-18569.
[http://dx.doi.org/10.1021/ja208068w] [PMID: 22047138]
[113]
Yang, F.; Wu, Y.; Zhu, Z.; Zhang, J.; Li, Y. Direct ortho-arylation of 2-arylbenzoxazoles via C–H activation. Tetrahedron, 2008, 64, 6782-6787.
[http://dx.doi.org/10.1016/j.tet.2008.04.099]
[114]
Yang, F.; Wu, Y.; Li, Y.; Wang, B.; Zhang, J. Modified palladium-catalyzed regioselective ortho-arylation of sp2 C–H bond substrates with a low catalyst loading. Tetrahedron, 2009, 65, 914-919.
[http://dx.doi.org/10.1016/j.tet.2008.11.001]
[115]
Stefane, B.; Zugelj, H.B.; Groselj, U.; Kuzman, P.; Svete, J.; Požgan, F. Quinazoline -directed C–H bond functionalization catalyzed by Ruthenium (II) carboxylate–construction of polyconjugated aryl-heteroaryl systems. Eur. J. Org. Chem., 2017, 2017, 1855-1864.
[http://dx.doi.org/10.1002/ejoc.201700097]
[116]
Gao, W.; Gong, C.; Yang, Q.; Yuan, J.; Xu, L.; Peng, Y. Rh(III)-catalyzed oxidative ortho-C–H alkylation of 2,4-diarylquinazoline with potassium alkyltrifluoroborates. Can. J. Chem., 2017, 95, 1052-1058.
[http://dx.doi.org/10.1139/cjc-2017-0258]
[117]
Wang, H.; Yu, S.; Qi, Z.; Li, X. Rh(III)-catalyzed C-H alkylation of arenes using alkylboron reagents. Org. Lett., 2015, 17(11), 2812-2815.
[http://dx.doi.org/10.1021/acs.orglett.5b01232] [PMID: 25972069]
[118]
Peng, P.; Wang, J.; Jiang, H.; Liu, H. Rhodium (III)-catalyzed site-selective C–H alkylation and arylation of pyridones using organoboron reagents. Org. Lett., 2016, 18(20), 5376-5379.
[http://dx.doi.org/10.1021/acs.orglett.6b02755] [PMID: 27736078]
[119]
Ping, Y.; Chen, Z.; Ding, Q.; Peng, Y. Rhodium (III)-catalyzed ortho-C–H alkylation of 2-arylbenzothiazoles and 2-arylthiazoles with potassium alkyltrifluoroborates. Synthesis, 2017, 49, 2015-2024.
[http://dx.doi.org/10.1055/s-0036-1588936]
[120]
Mirallai, S.I.; Koutentis, P.A. The Conversion of 4-anilinoquinazoline- and 3-aryl-4-imino-3,4-dihydro-quinazoline-2-carbonitriles into benzo[4,5]imidazo-[1,2-c]quinazoline-6-carbonitriles via oxidative and nonoxidative C-N couplings. J. Org. Chem., 2015, 80(16), 8329-8340.
[http://dx.doi.org/10.1021/acs.joc.5b01514] [PMID: 26252396]
[121]
Shen, C.; Wang, L.; Wen, M.; Shen, H.; Jin, J.; Zhang, P. Synthesis of benzimidazo[1,2-c]quinazolines via metal-free intramolecular C–H amination reaction. Ind. Eng. Chem. Res., 2016, 55, 3177-3181.
[http://dx.doi.org/10.1021/acs.iecr.5b04452]
[122]
Hu, L.; Xu, H.; Yang, Q.; Deng, Z.; Yu, C.Y.; Peng, Y. Quinazoline-directed selective ortho-iodination for the synthesis of 2-(2-iodoaryl)-4-arylquinazo-lines. J. Organomet. Chem., 2017, 843, 20-25.
[http://dx.doi.org/10.1016/j.jorganchem.2017.05.025]
[123]
Viveki, A.B.; Mhaske, S.B. Ruthenium-catalyzed regioselective alkenylation/tandem hydroamidative cyclization of unmasked quinazolinones using terminal alkynes. J. Org. Chem., 2018, 83(16), 8906-8913.
[http://dx.doi.org/10.1021/acs.joc.8b01143] [PMID: 29847951]
[124]
Zhang, Y.; Huang, J.; Deng, Z.; Muo, X.; Peng, Y. Rhodium (III)-catalyzed CH amination of 2-arylquinazolin-4 (3H)-one with N-alkyl-O-benzoyl-hydroxylamines. Tetrahedron, 2018, 74, 2330-2337.
[http://dx.doi.org/10.1016/j.tet.2018.03.051]
[125]
Sarkar, W.; Mishra, A.; Bhowmik, A.; Deb, I. Copper-mediated direct and selective C−H thiolation of quinazolinones. Asian J. Org. Chem., 2019, 8, 819-822.
[http://dx.doi.org/10.1002/ajoc.201900199]
[126]
Zhang, J.; Wang, X.; Chen, D.; Kang, Y.; Ma, Y.; Szostak, M. Synthesis of C6-substituted isoquinolino[1,2-b]quinazolines via Rh(III)-ctalyzed C-H annulation with sulfoxonium ylides. J. Org. Chem., 2020, 85(5), 3192-3201.
[http://dx.doi.org/10.1021/acs.joc.9b03065] [PMID: 31944108]