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

Abbasian       Sepideh; Kabirifard       Hassan; Mahdavi       Mohammad

doi:10.2174/1570178616666190514085642

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.

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[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] 

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DOI https://dx.doi.org/10.2174/1570178616666190514085642	Print ISSN 1570-1786
Publisher Name Bentham Science Publisher	Online ISSN 1875-6255

Letters in Organic Chemistry

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

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