A Review on the Syntheses and Applications of the 5H-chromeno[2,3- b]pyridines

Page: [28 - 53] Pages: 26

  • * (Excluding Mailing and Handling)

Abstract

5H-Chromeno[2,3-b]pyridine derivatives are a series of the most important compounds of chromenes with industrial, biological, and medicinal properties. These compounds are known as the privileged medicinal scaffold and can be synthesized by different methods such as multicomponent reactions (MCRs), Multicomponent coupling reactions (MCCRs), pot, atom, and step economy (PASE). In this review article, we have focused on the significant reactions for the syntheses and applications of 5H-chromeno[2,3-b] pyridines, including two-component reactions, three-component reactions, fourcomponent reactions, and multi-step reactions. This review is expected to serve as a useful conceptual overview and inspire the next generation to develop the different strategies for the preparation of 5HChromeno[ 2,3-b] pyridine derivatives.

Keywords: Chromenopyridines, privileged scaffold, multicomponent reactions, biological activity, antibacterial.

Graphical Abstract

[1]
Ren, Q.; Siau, W.Y.; Du, Z.; Zhang, K.; Wang, J. Chemistry, 2011, 17(28), 7781-7785.
[http://dx.doi.org/10.1002/chem.201100927] [PMID: 21618299]
[2]
Cheng, J.F.; Ishikawa, A.; Ono, Y.; Arrhenius, T.; Nadzan, A. Bioorg. Med. Chem. Lett., 2003, 13(21), 3647-3650.
[http://dx.doi.org/10.1016/j.bmcl.2003.08.025] [PMID: 14552749]
[3]
Bonsignore, L.; Loy, G.; Secci, D.; Calignano, A. Eur. J. Med. Chem., 1993, 28(6), 517-520.
[http://dx.doi.org/10.1016/0223-5234(93)90020-F]
[4]
Gourdeau, H.; Leblond, L.; Hamelin, B.; Desputeau, C.; Dong, K.; Kianicka, I.; Custeau, D.; Boudreau, C.; Geerts, L.; Cai, S.X.; Drewe, J.; Labrecque, D.; Kasibhatla, S.; Tseng, B. Mol. Cancer Ther., 2004, 3(11), 1375-1384.
[PMID: 15542776]
[5]
Ali, T.E.S. Phosphorus Sulfur., 2007, 182(6), 1717-1726.
[http://dx.doi.org/10.1080/10426500701313896]
[6]
Moon, D.O.; Kim, K.C.; Jin, C.Y.; Han, M.H.; Park, C.; Lee, K.J.; Park, Y.M.; Choi, Y.H.; Kim, G.Y. Int. Immunopharmacol., 2007, 7(2), 222-229.
[http://dx.doi.org/10.1016/j.intimp.2006.10.001] [PMID: 17178390]
[7]
Chen, Y.J.; Huang, S.M.; Tai, M.C.; Chen, J.T.; Lee, A.R.; Huang, R.Y.; Liang, C.M. Pharmacol. Rep., 2020, 72(1), 115-125.
[http://dx.doi.org/10.1007/s43440-019-00026-9] [PMID: 32016832]
[8]
Mladenović, M.; Mihailović, M.; Bogojević, S.; Matić, Nićiforović, N.; Mihailović, V.; Vuković, N.; Sukdolak, S.; Solujić, S. Int. J. Mol. Sci., 2011, 12(5), 2822-2841.
[PMID: 21686153]
[9]
Rueping, M.; Sugiono, E.; Merino, E. Chemistry, 2008, 14(21), 6329-6332.
[http://dx.doi.org/10.1002/chem.200800836] [PMID: 18576457]
[10]
Ramazani, A.; Ahmadi, Y.; Aghahosseini, H.; Joo, S.W. Phosphorus Sulfur Silicon Relat. Elem., 2016, 191(3), 354-358.
[http://dx.doi.org/10.1080/10426507.2015.1072193]
[11]
Ghoneim, A.A.; El-Farargy, A.F.; Abdelaziz, S. Nucleosides Nucleotides Nucleic Acids, 2014, 33(9), 583-596.
[http://dx.doi.org/10.1080/15257770.2014.912320] [PMID: 25105450]
[12]
Patel, A.A.; Lad, H.B.; Pandya, K.R.; Patel, C.V.; Brahmbhatt, D.I. Med. Chem. Res., 2013, 22, 4745-4754.
[http://dx.doi.org/10.1007/s00044-013-0489-4]
[13]
Jadhav, G.R.; Deshmukh, D.G.; Medhane, V.J.; Gaikwad, V.B.; Bholay, A.D. Heterocycl. Commun., 2016, 22(3), 123-130.
[http://dx.doi.org/10.1515/hc-2015-0215]
[14]
Mori, J.; Iwashima, M.; Takeuchi, M.; Saito, H. Chem. Pharm. Bull. (Tokyo), 2006, 54(3), 391-396.
[http://dx.doi.org/10.1248/cpb.54.391] [PMID: 16508200]
[15]
Jain, N.; Xu, J.; Kanojia, R.M.; Du, F.; Jian-Zhong, G.; Pacia, E.; Lai, M.T.; Musto, A.; Allan, G.; Reuman, M.; Li, X.; Hahn, D.; Cousineau, M.; Peng, S.; Ritchie, D.; Russell, R.; Lundeen, S.; Sui, Z. J. Med. Chem., 2009, 52(23), 7544-7569.
[http://dx.doi.org/10.1021/jm900146e] [PMID: 19366247]
[16]
Amr, A.G.; Mohamed, A.M.; Mohamed, S.F.; Abdel-Hafez, N.A.; Hammam, Ael-F. Bioorg. Med. Chem., 2006, 14(16), 5481-5488.
[http://dx.doi.org/10.1016/j.bmc.2006.04.045] [PMID: 16713269]
[17]
Bhat, M.A.; Siddiqui, N.; Khan, S.A. Acta Pol. Pharm., 2008, 65(2), 235-239.
[PMID: 18666431]
[18]
El-Sayed, R.; Fadda, A.A. J. Oleo Sci., 2016, 65(11), 929-940.
[http://dx.doi.org/10.5650/jos.ess15300] [PMID: 27803492]
[19]
Uesawa, Y.; Ishii-Nozawa, R.; Ishihara, M.; Kagaya, H.; Kanamoto, T.; Terakubo, S.; Nakashima, H.; Takao, K.; Sugita, Y.; Sakagami, H. Anticancer Res., 2014, 34(10), 5405-5411.
[PMID: 25275035]
[20]
Ryzhkova, Y.E.; Ryzhkov, F.V.; Elinson, M.N.; Vereshchagin, A.N.; Egorov, M.P. ARKIVOC, 2020, vi, 193-208.
[http://dx.doi.org/10.24820/ark.5550190.p011.220]
[21]
Banerjee, S.; Wang, J.; Pfeffer, S.; Ma, D.; Pfeffer, L.M.; Patil, S.A.; Li, W.; Miller, D.D. Molecules, 2015, 20(9), 17152-17165.
[http://dx.doi.org/10.3390/molecules200917152] [PMID: 26393554]
[22]
Elinson, M.N.; Vereshchagin, A.N.; Anisina, Y.E.; Egorov, M.P.P. Compd., 2020, 40(1), 108-115.
[23]
Chake, A.; Zribi, F.; Nepveu, F.; Chabchoub, F. Chin. Chem. Lett., 2014, 25(8), 1207-1210.
[http://dx.doi.org/10.1016/j.cclet.2014.03.048]
[24]
Heravi, M.M.; Ansari, P.; Saeedi, M.; Tavakoli-Hosseini, N.; Karimi, N. Bull. Chem. Soc. Ethiop., 2011, 25(2), 315-320.
[http://dx.doi.org/10.4314/bcse.v25i2.65915]
[25]
Elinson, M.N.; Vereshchagin, A.N.; Anisina, Y.E.; Krymov, S.K.; Fakhrutdinov, A.N.; Egorov, M.P. Monatsh. Chem., 2019, 150, 1073-1078.
[http://dx.doi.org/10.1007/s00706-019-02388-5]
[26]
Kamboj, S.; Singh, R. Arab. J. Sci. Eng., 2022, 47, 75-111.
[http://dx.doi.org/10.1007/s13369-021-05858-3]
[27]
Evdokimov, N.M.; Kireev, A.S.; Yakovenko, A.A.; Antipin, M.Y.; Magedov, I.V.; Kornienko, A. J. Org. Chem., 2007, 72(9), 3443-3453.
[http://dx.doi.org/10.1021/jo070114u] [PMID: 17408286]
[28]
Choi, J.S.; Shi, S.C. Biomol. Ther. (Seoul), 2008, 16(3), 210-214.
[http://dx.doi.org/10.4062/biomolther.2008.16.3.210]
[29]
Katsarou, M.E.; Efthimiadou, E.K.; Psomas, G.; Karaliota, A.; Vourloumis, D. J. Med. Chem., 2008, 51(3), 470-478.
[http://dx.doi.org/10.1021/jm7013259] [PMID: 18205294]
[30]
Tang, G.M.; Han, J.Y.; Wang, Y.T.; Cui, Y.Z.; Ng, S.W. Polyhedron, 2017, 133(5), 336-342.
[http://dx.doi.org/10.1016/j.poly.2017.05.031]
[31]
Anderson, D.R.; Hegde, S.; Reinhard, E.; Gomez, L.; Vernier, W.F.; Lee, L.; Liu, S.; Sambandam, A.; Snider, P.A.; Masih, L. Bioorg. Med. Chem. Lett., 2005, 15(6), 1587-1590.
[http://dx.doi.org/10.1016/j.bmcl.2005.01.067] [PMID: 15745802]
[32]
Verma, C.; Olasunkanmi, L.O.; Obot, I.B.; Ebensob, E.E.; Quraishi, M.A. RSC Advances, 2016, 6, 53933-53948.
[http://dx.doi.org/10.1039/C6RA04900A]
[33]
Zhang, C.H.; Huang, R.; Hu, X.M.; Lin, J.; Yan, S.J. J. Org. Chem., 2018, 83(9), 4981-4989.
[http://dx.doi.org/10.1021/acs.joc.8b00099] [PMID: 29648823]
[34]
Elinson, M.; Vereshchagin, A.N.; Anisina, Y.E.; Goloveshkin, A.S.; Ushakov, I.E.; Egorov, M.P. Russ. Chem. Bull., 2018, 67, 1695-1703.
[http://dx.doi.org/10.1007/s11172-018-2278-1]
[35]
Nikookar, H.; Moghimi, S.; Sayahi, M.H.; Mahdavi, M.; Ranjbar, P.R.; Firoozpour, L.; Foroumadi, A. Comb, 2018, 21(5), 344-348.
[http://dx.doi.org/10.2174/1386207321666180524110635]
[36]
Gorokhov, V.Y.; Makhova, T. Russ. Chem. Bull., 2020, 69, 425-434.
[http://dx.doi.org/10.1007/s11172-020-2781-z]
[37]
(a) Yavari, I.; Ramazani, A. Phosphorus Sulfur, 1997, 130(1), 73-77.
[http://dx.doi.org/10.1080/10426509708033699];
(b) Mohamadpour, F.; Feilizadeh, M. Chem. Methodol., 2020, 4(5), 647-659.;
(c) Belgasem Mezoughi, A.; Abdussalam Mohammed, W.; Ettarhouni, Z.O. J. Chem. Rev., 2021, 3(3), 196-218.
[38]
(a) Azizmohammadi, M.; Khoobi, M.; Ramazani, A.; Emami, S.; Zarrin, A.; Firuzi, O.; Miri, R.; Shafiee, A. Eur. J. Med. Chem., 2013, 59, 15-22.
[http://dx.doi.org/10.1016/j.ejmech.2012.10.044] [PMID: 23202485];
(b) Sapra, R.; Patel, D.; Meshram, D. J. Med. Chem. Sci., 2020, 3(1), 71-78.
[http://dx.doi.org/10.26655/JMCHEMSCI.2020.1.9];
(c) Asirvatham, S.; Thakor, E.; Jain, H. J. Chem. Rev., 2021, 3(4), 247-272.
[http://dx.doi.org/10.22034/jcr.2021.295839.1123]
[39]
Khoobi, M.; Ma’mani, L.; Rezazadeh, F.; Zareie, Z.; Foroumadi, A.; Ramazani, A.; Shafiee, A. J. Mol. Catal. Chem., 2012, 359, 74-80.
[http://dx.doi.org/10.1016/j.molcata.2012.03.023]
[40]
(a) Ramazani, A.; Shajari, N.; Mahyari, A.; Ahmadi, Y. Mol. Divers., 2011, 15(2), 521-527.
[http://dx.doi.org/10.1007/s11030-010-9275-0] [PMID: 20812029];
(b) Irannejad-Gheshlaghchaei, N.; Zare, A.; Banaei, A.; Kaveh, H.; Varavi, N. Chem. Methodol., 2020, 4(4), 400-407.
[http://dx.doi.org/10.33945/SAMI/CHEMM.2020.4.3];
(c) Muhiebes, R.M.; Al-Tamimi, E.O. Chem. Methodol., 2021, 5(5), 416-421.;
(d) Fadel, Z.H.; Al-Azzawi, A.M. Chem. Methodol., 2021, 5(6), 464-470.;
(e) Baghernejad, B.; Nazari, L. Chem. Commun. (Camb.), 2021, 3(5), 319-326.;
(f) Baghernejad, B.; Rostami Harzevili, M. Chem. Methodol., 2021, 5(2), 90-95.;
(g) Karimi, A.H.; Hekmat-Ara, A.; Zare, A.; Barzegar, M.; Khanivar, R.; Sadeghi-Takallo, M. Chem. Commun. (Camb.), 2021, 3(6), 360-368.;
(h) Nikpassand, M.; Zare Fekri, L. Chem. Methodol., 2020, 4(4), 437-446.
[http://dx.doi.org/10.33945/SAMI/CHEMM.2020.4.6]
[41]
(a) Ramazani, A.; Mahyari, A.T.; Rouhani, M.; Rezaei, A. Tetrahedron Lett., 2009, 50(40), 5625-5627.
[http://dx.doi.org/10.1016/j.tetlet.2009.07.115];
(b) Khazaei, A.; Gohari-Ghalil, F.; Tavasoli, M.; Rezaei-Gohar, M.; Moosavi-Zare, A.R. Chem. Methodol, 2020, 4(5), 543-553.;
(c) Kamali, F.; Shirini, F. Chem. Commun. (Camb.), 2021, 3(4), 278-290.;
(d) Fernandes, C.; Park, S.H.; Sloop, J.; Wilmott, K. Chem. Methodol., 2020, 4(5), 554-564.;
(e) Albadi, J.; Samimi, H.A.; Momeni, A.R. Chem. Methodol, 2020, 4(5), 565-571.;
(f) Moosavi-Zare, A.R.; Zolfigol, M.A.; Rezanejad, Z. Chem. Methodol., 2020, 4(5), 614-622.;
(g) Hoseini, Z.; Davoodnia, A.; Pordel, M. Advanced Journal of Chemistry, Section A, 2021, 4(1), 68-77.;
(h) Rehan, T.A.; Al-Lami, N.; Khudhair, N.A. Chem. Methodol., 2021, 5(4), 285-295.
[42]
(a) Baghernejad, B.; Zareie, A.; Asian, J. Green Chem., 2021, 5(4), 343-350.;
(b) Rezayati, S.; Kalantari, F.; Ramazani, A.; Sajjadifar, S.; Aghahosseini, H.; Rezaei, A. Inorg. Chem., 2022, 61(2), 992-1010.
[http://dx.doi.org/10.1021/acs.inorgchem.1c03042] [PMID: 34962386];
(c) Singha, R.; Brahman, D.; Sinha, B.; Ghosh, P.; Asian, J. Green Chem., 2021, 5(1), 91-110.;
(d) Fallah-Mehrjardi, M.; Foroughi, M.; Banitaba, S.H.; Asian, J. Green Chem., 2020, 4(1), 75-86.;
(e) Rezayati, S.; Ramazani, A.; Sajjadifar, S.; Aghahosseini, H.; Rezaei, A. ACS Omega, 2021, 6(39), 25608-25622.
[http://dx.doi.org/10.1021/acsomega.1c03672] [PMID: 34632217];
(f) Baghernejad, B.; Talebi, M.; Asian, J. Green Chem., 2021, 5(4), 368-377.;
(g) Majidi Arlan, F.; Javahershenas, R.; Khalafy, J. Asian J. Nanosci. Mater., 2020, 3(3), 238-250.;
(h) Kalantari, F.; Rezayati, S.; Ramazani, A.; Aghahosseini, H.; Ślepokura, K.; Lis, T. ACS Appl. Nano Mater., 2022, 5(2), 1783-1797.
[http://dx.doi.org/10.1021/acsanm.1c03169];
(i) Pagore, V.P.; Jadhav, V.B.; Bajad, P.N.; Pawar, R.P.; Asian, J. Green Chem., 2020, 4(4), 379-386. (j) Yadollahzadeh. K. Asian J. Nanosci. Mater., 2021, 4(1), 81-94.
[43]
(a) Butler, R.N.; Coyne, A.G. Org. Biomol. Chem., 2016, 14(42), 9945-9960.
[http://dx.doi.org/10.1039/C6OB01724J] [PMID: 27714194];
(b) Rezayati, S.; Salehi, E.; Hajinasiri, R.; Afshari Sharif Abad, S. C. R. Chim., 2017, 20(5), 554-558.
[http://dx.doi.org/10.1016/j.crci.2016.07.004];
(c) Rezayati, S.; Hajinasiri, R.; Erfani, Z. Res. Chem. Intermed., 2016, 42, 2567-2576.
[http://dx.doi.org/10.1007/s11164-015-2168-1]
[44]
Elinson, M.N.; Nasybullin, R.F.; Ryzhkov, F.V.; Zaimovskaya, T.A.; Nikishin, G.I. Monatshefte für Chemie-Chemical Monthly, 2015, 146, 631-635.
[http://dx.doi.org/10.1007/s00706-014-1318-2]
[45]
Nouri, H.; Cadiou, C.; HenryaIsabelle, A.; Déchamps-Oliviera, I.; Ternane, R.; Trabelsi-Ayadi, M.; Lemercier, G.; Chuburu, F. J. Lumin., 2014, 148, 202-206.
[http://dx.doi.org/10.1016/j.jlumin.2013.12.027]
[46]
de Silva, A.P.; Gunaratne, H.Q.; Gunnlaugsson, T.; Huxley, A.J.M.; McCoy, C.P.; Rademacher, J.T.; Rice, T.E. Chem. Rev., 1997, 97(5), 1515-1566.
[http://dx.doi.org/10.1021/cr960386p] [PMID: 11851458]
[47]
Weinstein, D.S.; Gong, H.; Doweyko, A.M.; Cunningham, M.; Habte, S.; Wang, H. J. Med. Chem., 2011, 54(20), 7318-7333.
[http://dx.doi.org/10.1021/jm200879j] [PMID: 21899328]
[48]
Gong, H.; Yang, Z. Bioorg. Med. Chem. Lett., 2014, 24(15), 3268-3273.
[http://dx.doi.org/10.1016/j.bmcl.2014.06.010] [PMID: 24980053]
[49]
Osyanin, V.A.; Osipov, D.V.; Klimochkin, Y.N. Tetrahedron, 2012, 68(27-28), 5612-5618.
[http://dx.doi.org/10.1016/j.tet.2012.04.065]
[50]
Bardasov, I.N.; Alekseeva, A.Y.; Malyshkina, N.L.; Ershov, O.V.; Grishanov, D.A. Russ. J. Org. Chem., 2016, 52, 830-833.
[http://dx.doi.org/10.1134/S1070428016060117]
[51]
Yunnikova, L.P.; Gorokhov, V.Y.; Makhova, T.V.; Aleksandrova, G.A. Pharm. Chem. J., 2013, 47, 139-141.
[http://dx.doi.org/10.1007/s11094-013-0912-7]
[52]
Festa, A.A.; Storozhenko, O.A.; Bella Ndoutoume, D.R.; Varlamov, A.V.; Voskressensky, L.G. Mendeleev Commun., 2017, 27, 451-453.
[http://dx.doi.org/10.1016/j.mencom.2017.09.006]
[53]
Elinson, M.N.; Gorbunov, S.V.; Vereshchagin, A.N.; Nasybullin, R.F.; Goloveshkin, A.S.; Bushmarinov, I.S.; Egorov, M.P. Tetrahedron, 2014, 70(45), 8559-8563.
[http://dx.doi.org/10.1016/j.tet.2014.09.066]
[54]
Clarke, P.A.; Santos, S.; Martin, W.H. Green Chem., 2007, 9(5), 438-440.
[http://dx.doi.org/10.1039/b700923b]
[55]
Hayashi, Y. Chem. Sci. (Camb.), 2016, 7, 866-880.
[http://dx.doi.org/10.1039/C5SC02913A]
[56]
Bhattacharyya, P.; Pradhan, K.; Paul, S.; Das, A.R. Tetrahedron Lett., 2012, 53(35), 4687-4691.
[http://dx.doi.org/10.1016/j.tetlet.2012.06.086]
[57]
Mishra, S.; Ghosh, R. Synth. Commun., 2012, 42(15), 2229-2244.
[http://dx.doi.org/10.1080/00397911.2011.555284]
[58]
Ghasemzadeh, M.A.; Abdollahi-Basir, M.H.; Babaei, M. Green Chem. Lett. Rev., 2015, 8(3-4), 40-49.
[http://dx.doi.org/10.1080/17518253.2015.1107139]
[59]
Elinson, M.N.; Ilovaisky, A.I.; Merkulova, V.M.; Belyakov, P.A.; Chizhov, A.O.; Nikishin, G.I. Tetrahedron, 2010, 66(23), 4043-4048.
[http://dx.doi.org/10.1016/j.tet.2010.04.024]
[60]
Vereshchagin, A.N.; Elinson, M.N.; Anisina, Y.E.; Ryzhkov, F.V.; Goloveshkin, A.S.; Bushmarinov, I.S.; Zlotin, S.G. Mendeleev Commun., 2015, 6, 424-426.
[http://dx.doi.org/10.1016/j.mencom.2015.11.008]
[61]
Poupaert, J.; Carato, P.; Colacino, E.; Yous, S. Curr. Med. Chem., 2005, 12(7), 877-885.
[http://dx.doi.org/10.2174/0929867053507388] [PMID: 15853716]
[62]
Perez-Fernandez, R.; Goya, P.; Elguero, J. ARKIVOC, 2014, ii, 233-293.
[63]
Wise, L.D.; Butler, D.E.; DeWald, H.A.; Lustgarten, D.M.; Pattison, I.C.; Schweiss, D.N.; Coughenour, L.L.; Downs, D.A.; Heffner, T.G.; Pugsley, T.A. J. Med. Chem., 1987, 30(10), 1807-1812.
[http://dx.doi.org/10.1021/jm00393a021] [PMID: 2888897]
[64]
Singh, P.; Paul, K.; Holzer, W. Bioorg. Med. Chem., 2006, 14(14), 5061-5071.
[http://dx.doi.org/10.1016/j.bmc.2006.02.046] [PMID: 16554161]
[65]
Kees, K.L.; Fitzgerald, J.J., Jr; Steiner, K.E.; Mattes, J.F.; Mihan, B.; Tosi, T.; Mondoro, D.; McCaleb, M.L. J. Med. Chem., 1996, 39(20), 3920-3928.
[http://dx.doi.org/10.1021/jm960444z] [PMID: 8831758]
[66]
Herk, T.V.; Brussee, J.; van den Nieuwendijk, A.M.C.H.; van der Klein, P.A.M.; IJzerman, A.P.; Stannek, C.; Burmeister, A.; Lorenzen, A. J. Med. Chem., 2003, 46(18), 3945-3951.
[http://dx.doi.org/10.1021/jm030888c] [PMID: 12930155]
[67]
Elinson, M.N.; Vereshchagin, A.N.; Anisina, Y.E.; Fakhrutdinov, A.N.; Goloveshkin, A.S.; Egorov, M.P. J. Fluor. Chem., 2018, 213, 31-36.
[http://dx.doi.org/10.1016/j.jfluchem.2018.06.008]
[68]
Elinson, M.N.; Vereshchagin, A.N.; Anisina, Y.E.; Fakhrutdinov, A.N.; Goloveshkin, A.S.; Egorov, M.P. Eur. J. Org. Chem., 2019, 2019(26), 4171-4178.
[http://dx.doi.org/10.1002/ejoc.201900240]
[69]
Quin, L.D. A guide to organophosphorus chemistry; John Wiley & Sons, 2000.
[70]
Hildebrand, R. The Role of Phosphonates in Living Systems, 1983, 139-169.
[http://dx.doi.org/10.1201/9781351076470]
[71]
Benbrook, C.M. Environ. Sci. Eur., 2016, 28(1), 3.
[http://dx.doi.org/10.1186/s12302-016-0070-0] [PMID: 27752438]
[72]
Paliwal, P.; Jetti, S.R.; Bhatewara, A.; Kadre, T.; Jain, S. ISRN Org. Chem., 2013, 2013, 526173.
[http://dx.doi.org/10.1155/2013/526173] [PMID: 24052863]
[73]
Gupta, S.; Khurana, J.M. Green Chem., 2017, 19, 4153-4156.
[http://dx.doi.org/10.1039/C7GC01463E]
[74]
Olyaei, A.; Shahsavari, M.S.; Sadeghpour, M. Res. Chem. Intermed., 2018, 44, 943-956.
[http://dx.doi.org/10.1007/s11164-017-3145-7]
[75]
Zhang, W.; Wang, J.; Mao, J.; Hu, L.; Wu, X.; Guo, C. Tetrahedron Lett., 2016, 57, 1985-1989.
[http://dx.doi.org/10.1016/j.tetlet.2016.03.081]
[76]
Chung, S.T.; Huang, W.H.; Huang, C.K.; Liu, F.C.; Huang, R.Y.; Wu, C.C.; Lee, A.R. Res. Chem. Intermed., 2016, 42, 1195-1215.
[http://dx.doi.org/10.1007/s11164-015-2081-7]
[77]
Vereshchagin, A.N.; Elinson, M.N.; Anisina, Y.E.; Ryzhkov, F.V.; Novikov, R.A.; Egorov, M.P. ChemistrySelect, 2017, 2(17), 4593-4597.
[http://dx.doi.org/10.1002/slct.201700606]
[78]
Ansari, K.; Quraishi, M.; Singh, A. J. Assoc. Arab Univ. Basic Appl. Sci., 2017, 22, 45-54.
[79]
Zhang, M.; Chen, M.N.; Zhang, Z.H. Adv. Synth. Catal., 2019, 361(22), 5182-5190.
[http://dx.doi.org/10.1002/adsc.201900994]
[80]
Safaei-Ghomi, J.; Tavazo, M.; Vakili, M.R.; Shahbazi-Alavi, H. J. Sulfur Chem., 2017, 38(3), 236-248.
[http://dx.doi.org/10.1080/17415993.2016.1275633]
[81]
Sudheesh, N.; Sharma, S.K.; Shukla, R.S. J. Mol. Catal. Chem., 2010, 321(1-2), 77-82.
[http://dx.doi.org/10.1016/j.molcata.2010.02.005]
[82]
Abdelmoniem, A.M.; Ghozlan, S.A.S.; Abdelmoniem Ahmed, D.M.; Elwahy, H.M.; Abdelhamid, I.A. J. Heterocycl. Chem., 2017, 54(5), 2844-2849.
[http://dx.doi.org/10.1002/jhet.2890]
[83]
Rajanarendar, E.; Ramakrishna, S.; Kishore, B. J. Heterocycl. Chem., 2014, 51(5), 1415-1420.
[http://dx.doi.org/10.1002/jhet.1836]
[84]
Dineen, T.A.; Chen, K.; Cheng, A.C.; Derakhchan, K.; Epstein, O.; Esmay, J.; Hickman, D.; Kreiman, C.E.; Marx, I.E.; Wahl, R.C.; Wen, P.H.; Weiss, M.M.; Whittington, D.A.; Wood, S.; Fremeau, R.T., Jr; White, R.D.; Patel, V.F. J. Med. Chem., 2014, 57(23), 9811-9831.
[http://dx.doi.org/10.1021/jm5012676] [PMID: 25363711]