Generic placeholder image

Letters in Organic Chemistry

Author(s): Abbasian Sepideh, Kabirifard Hassan* and Mahdavi Mohammad

DOI: 10.2174/1570178616666190514085642

DownloadDownload PDF Flyer Cite As
Pd-Catalyzed Carbonylation-cyclization of N′-(2-bromophenyl)benzamidines by Chloroform as a CO Precursor for the Synthesis of Quinazolin- 4(3H)-ones

Page: [303 - 308] Pages: 6

  • * (Excluding Mailing and Handling)

Explore Articles
About Journal
For Authors
For Editors
For Reviewers

Abstract

We present an efficient method for the synthesis of quinazolin-4(3H)-ones via Pdcatalyzed carbonylation-cyclization of N′-(2-bromophenyl)benzamidines. Chloroform cleanly generated CO under mild conditions. This method allows for the carbonylation-cyclization of N′-(2- bromophenyl)benzamidines in the presence of Pd(OAc)2 to give quinazolin-4(3H)-ones in good to excellent yields.

Keywords: Quinazolin-4(3H)-one, N′-(2-Bromophenyl)benzamidine, chloroform, palladium acetate, carbonylation, anti-ulcer agents.

Graphical Abstract

[1]
Tereshima, K.; Shimamura, H.; Kawase, A.; Tanaka, Y.; Tanimura, T.; Kamisaki, T.; Ishizuka, Y.; Sato, M. Chem. Pharm. Bull. (Tokyo), 1995, 43, 2021-2023.
[http://dx.doi.org/10.1248/cpb.43.2021] [PMID: 8575039]
[2]
Wolfe, J.F.; Rathman, T.L.; Sleevi, M.C.; Campbell, J.A.; Greenwood, T.D. J. Med. Chem., 1990, 33(1), 161-166.
[http://dx.doi.org/10.1021/jm00163a027] [PMID: 2296016]
[3]
Kurogi, Y.; Inoue, Y.; Tsutsumi, K.; Nakamura, S.; Nagao, K.; Yoshitsugu, H.; Tsuda, Y. J. Med. Chem., 1996, 39(7), 1433-1437.
[http://dx.doi.org/10.1021/jm9506938] [PMID: 8691473]
[4]
Cao, S.L.; Feng, Y.P.; Jiang, Y.Y.; Liu, S.Y.; Ding, G.Y.; Li, R.T. Bioorg. Med. Chem. Lett., 2005, 15(7), 1915-1917.
[http://dx.doi.org/10.1016/j.bmcl.2005.01.083] [PMID: 15780632]
[5]
Ozaki, K.; Yamada, Y.; Oine, T.; Ishizuka, T.; Iwasawa, Y. Studies on 4(1H)-quinazolinones. 5. Synthesis and antiinflammatory activity of 4(1H)-quinazolinone derivatives. J. Med. Chem., 1985, 28(5), 568-576.
[http://dx.doi.org/10.1021/jm50001a006] [PMID: 3872940]
[6]
Kuneš, J.; Bažant, 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]
[7]
Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett., 1999, 40, 2175-2178.
[http://dx.doi.org/10.1016/S0040-4039(99)00142-2]
[8]
Koepfli, J.B.; Mead, J.F.; Brockman, J.A. Jr. J. Am. Chem. Soc., 1947, 69, 1837-1837.
[http://dx.doi.org/10.1021/ja01199a513]
[9]
Jang, C.S.; Fu, F.Y.; Wang, C.Y.; Huang, K.C.; Lu, G.; Thou, T.C. Science, 1946, 103, 59-59.
[http://dx.doi.org/10.1126/science.103.2663.59-b]
[10]
Couture, A.; Cornet, H.; Grandclaudon, P. Synthesis, 1991, 1009-1010.
[http://dx.doi.org/10.1055/s-1991-26632]
[11]
Adib, M.; Sheikhi, E.; Bijanzadeh, H.R. Synlett, 2012, 85-88.
[http://dx.doi.org/10.1055/s-0031-1290098]
[12]
Vidyacharan, S. Chaitra, N.C.; Sagar, A.; Sharada, D.S. Synth. Commun., 2015, 45, 898-907.
[http://dx.doi.org/10.1080/00397911.2014.992076]
[13]
Liu, J.F.; Lee, J.; Dalton, A.M.; Bi, G.; Yu, L.; Baldino, C.M.; McElory, E.; Brown, M. Tetrahedron Lett., 2005, 46, 1241-1244.
[http://dx.doi.org/10.1016/j.tetlet.2005.01.008]
[14]
Giri, R.; Lam, J.K.; Yu, J.Q. J. Am. Chem. Soc., 2010, 132(2), 686-693.
[http://dx.doi.org/10.1021/ja9077705] [PMID: 20000840]
[15]
Connolly, D.J.; Guiry, P.J. Synlett, 2001, 1707-1710.
[http://dx.doi.org/10.1055/s-2001-18080]
[16]
Snider, B.B.; Zeng, H. Heterocycles, 2003, 61, 173-182.
[http://dx.doi.org/10.3987/COM-03-S12]
[17]
Wang, L.; Wang, Y.; Chen, M.; Ding, M.W. Adv. Synth. Catal., 2014, 356, 1098-1104.
[http://dx.doi.org/10.1002/adsc.201300950]
[18]
Abdel-Jalil, R.J.; Voelter, W.; Saeed, M. Tetrahedron Lett., 2004, 45, 3475-3476.
[http://dx.doi.org/10.1016/j.tetlet.2004.03.003]
[19]
Srishylam, V.; Devanna, N.; Rao, M.B.; Mulakayala, N. Tetrahedron Lett., 2017, 58, 2889-2892.
[http://dx.doi.org/10.1016/j.tetlet.2017.06.026]
[20]
He, L.; Li, H.; Neumann, H.; Beller, M.; Wu, X.F. Angew. Chem. Int. Ed., 2014, 53, 1420-1424.
[http://dx.doi.org/10.1002/anie.201308756]
[21]
Gadge, S.T.; Bhanage, B.M. RSC Advances, 2014, 4, 10367-10389.
[http://dx.doi.org/10.1039/c3ra46273k]
[22]
Omae, I. Coord. Chem. Rev., 2011, 255, 139-160.
[http://dx.doi.org/10.1016/j.ccr.2010.08.001]
[23]
Morimoto, T.; Kakiuchi, K. Angew. Chem. Int. Ed., 2004, 43, 5580-5588.
[http://dx.doi.org/10.1002/anie.200301736]
[24]
Fang, X.; Li, H.; Jackstell, R.; Beller, M. J. Am. Chem. Soc., 2014, 136(45), 16039-16043.
[http://dx.doi.org/10.1021/ja507530f] [PMID: 25325791]
[25]
Xu, T.; Alper, H. J. Am. Chem. Soc., 2014, 136(49), 16970-16973.
[http://dx.doi.org/10.1021/ja508588b] [PMID: 25283812]
[26]
Jackstell, R.; Fang, X.; Beller, M. Angew. Chem. Int. Ed., 2013, 52, 14089-14093.
[http://dx.doi.org/10.1002/anie.201308455]
[27]
Hermange, P.; Lindhardt, A.T.; Taaning, R.H.; Bjerglund, K.; Lupp, D.; Skrydstrup, T. J. Am. Chem. Soc., 2011, 133(15), 6061-6071.
[http://dx.doi.org/10.1021/ja200818w] [PMID: 21446732]
[28]
Escot, C.; Nielsen, D.U.; Makarov, I.S.; Lindhardt, A.T.; Daasbjerg, K.; Skrydstrup, T. J. Am. Chem. Soc., 2014, 136(16), 6142-6147.
[http://dx.doi.org/10.1021/ja502911e] [PMID: 24702475]
[29]
Buchwald, S.L.; Skrydstrup, T.; Friis, S.D. Org. Lett., 2014, 16, 4296-4299.
[http://dx.doi.org/10.1021/ol502014b] [PMID: 25090373]
[30]
Bhanage, B.M.; Bhatte, K.D.; Wagh, Y.S.; Sawant, D.S. J. Org. Chem., 2011, 76, 5489-5494.
[http://dx.doi.org/10.1021/jo200754v] [PMID: 21618964]
[31]
Friis, S.D.; Taaning, R.H.; Lindhardt, A.T.; Skrydstrup, T. J. Am. Chem. Soc., 2011, 133(45), 18114-18117.
[http://dx.doi.org/10.1021/ja208652n] [PMID: 22014278]
[32]
Odell, L.R.; Russo, F.; Larhed, M. Synlett, 2012, 23, 685-698.
[http://dx.doi.org/10.1055/s-0031-1290350]
[33]
Odell, L.R.; Fransson, R.; Wieckowska, A. J. Org. Chem., 2011, 76, 978-981.
[http://dx.doi.org/10.1021/jo102151u] [PMID: 21229975]
[34]
Grushin, V.V.; Alper, H. Organometallics, 1993, 12, 3846-3850.
[http://dx.doi.org/10.1021/om00034a016]
[35]
Gockel, S.N.; Hull, K.L. Org. Lett., 2015, 17(13), 3236-3239.
[http://dx.doi.org/10.1021/acs.orglett.5b01385] [PMID: 26090688]
[36]
Baelen, G.V.; Kuijer, S.; Rycek, L.; Sergeyev, S.; Janssen, E.; de Kanter, F.J.J.; Maes, E. Ruijter, B.U.W.; Orru, R.V.A. Chemistry, 2011, 17, 15039-15044.
[PMID: 22125085]
[37]
Davoodnia, A.; Allameh, S.; Fakhari, A.R.; Tavakoli-Hoseini, N. Chin. Chem. Lett., 2010, 21, 550-553.
[http://dx.doi.org/10.1016/j.cclet.2010.01.032]
[38]
Bakavoli, M.; Shiri, A.; Ebrahimpour, Z.; Rahimizadeh, M. Chin. Chem. Lett., 2008, 19, 1403-1406.
[http://dx.doi.org/10.1016/j.cclet.2008.07.016]
[39]
Chen, J.; Wu, D.; He, F.; Liu, M.; Wu, H.; Ding, J.; Su, W. Tetrahedron Lett., 2008, 49, 3814-3818.
[http://dx.doi.org/10.1016/j.tetlet.2008.03.127]
[40]
Bhat, B.A.; Sahu, D.P. Synth. Commun., 2004, 34, 2169-2176.
[http://dx.doi.org/10.1081/SCC-120038496]
[41]
Kausar, N.; Roy, I.; Chattopadhyay, D.; Das, A.R. RSC Advances, 2016, 6, 22320-22330.
[http://dx.doi.org/10.1039/C6RA00388E]
[42]
Roy, A.D.; Subramanian, A.; Roy, R. J. Org. Chem., 2006, 71(1), 382-385.
[http://dx.doi.org/10.1021/jo0518912] [PMID: 16388665]