Abstract
We have developed a KOH-promoted transition-metal-free synthesis of 2-substituted 4(3H)-quinazolinones from anthranilamides and benzyl alcohols or cinnamyl alcohol with air as oxidant. The protocol is simple, practical, and cost saving.
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Eguchi S (2006) Top Heterocycl Chem 6:113
Demeunynck M, Baussanne I (2013) Curr Med Chem 20:794
Patil DA, Patil PO, Patil GB, Surana SJ (2011) Mini Rev Med Chem 11:633
Xia Y, Yang ZY, Hour MJ, Kuo SC, Xia P, Bastow KF, Nakanishi Y, Nampoothiri P, Hackl T, Hamel E, Lee KH (2001) Bioorg Med Chem Lett 11:1193
Alagarsamy V, Raja SV, Dhanabal K (2007) Bioorg Med Chem 15:235
Selvam P, Girija K, Nagarajan G, De Clerco E (2005) Indian J Pharm Sci 67:484
Lazzaro JT, Paternain AV, Lerma J, Chenard BL, Ewing FE, Huang J, Welch WM, Ganong AH, Menniti FS (2002) Neuropharmacol 42:143
Liang JL, Cha HC, Jahng Y (2011) Molecules 16:4861
Chen AL, Chen KK (1933) J Am Pharm Assoc 22:716
Mohanta PK, Kim K (2002) Tetrahedron Lett 43:3993
Wattanapiromsakul C, Forster PI, Waterman PG (2003) Phytochem 64:609
Michael JP (2008) Nat Prod Rep 25:166
Mhaske SB, Argade NP (2006) Tetrahedron 62:9787
Connolly DJ, Cusack D, O’Sullivan TP, Guiry PJ (2005) Tetrahedron 61:10153
Imai Y, Sato S, Takasawa R, Ueda M (1981) Synthesis 1981:35
Hanusek J, Sedlak M, Simunek P, Sterba V (2002) Eur J Org Chem 2002:1855
Blackburn C, Achab A, Elder A, Ghosh S, Guo J, Harriman G, Jones M (2005) J Org Chem 70:10206
Zhu Y-P, Fei Z, Liu M-C, Jia F-C, Wu A-X (2013) Org Lett 15:378
Abdel-Jalil RJ, Voelter W, Saeed M (2004) Tetrahedron Lett 45:3475
Wang G-W, Miao C-B, Kang H (2006) Bull Chem Soc Japan 79:1426
Wang X-S, Yang K, Zhang M-M, Yao C-S (2010) Synth Commun 40:2633
Zhan D, Li T, Zhang X, Dai C, Wei H, Zhang Y, Zeng Q (2013) Synth Commun 43:2493
Zhan D, Li T, Wei H, Weng W, Ghandi K, Zeng Q (2013) RSC Adv 3:9325
Kim NY, Cheon C-H (2014) Tetrahedron Lett 55:2340
Takeuchi H, Haguvara S, Eguchi S (1989) Tetrahedron 45:6375
Connolly DJ, Guiry PJ (2001) Synlett 11:1707
Xu W, Jin Y, Liu H, Jiang Y, Fu H (2011) Org Lett 13:1274
Wei H, Li T, Zhou Y, Zhou L, Zeng Q (2013) Synthesis 45:3349
Chen J, Wu D, He F, Liu M, Wu H, Ding J, Su W (2008) Tetrahedron Lett 49:3814
Mohammadi AA, SadatHossini SS (2011) Chin J Chem 29:1982
Zhou J, Fang J (2011) J Org Chem 76:7730
Watson AJA, Maxwell AC, Williams JM (2012) J Org Biomol Chem 10:240
Hikawa H, Ino Y, Suzuki H, Yokoyama Y (2012) J Org Chem 77:7046
Sharif M, Opalach J, Langer P, Beller M, Wu MF (2014) RSC Adv 4:8
Ge W, Zhu X, Wei Y (2013) RSC Adv 3:10817
Schreiner PR (2003) Chem Soc Rev 32:289
Dalko PI, Moisan L (2001) Angew Chem Int Ed 40:3726
Beller M, Breindl C, Riermeier TH, Tillack A (2001) J Org Chem 66:1403
Yuan Y, Thomé I, Kim SH, Chen D, Beyer A, Bonnamour J, Zuidema E, Chang S, Bolm C (2010) Adv Synth Catal 352:2892
Zhao J, Zhao Y, Fu H (2011) Angew Chem Int Ed 50:3769
Pirali T, Zhang F, Miller AH, Head JL, McAusland D, Greaney MF (2012) Angew Chem Int Ed 51:1006
Dai C, Sun XF, Tu XZ, Wu L, Zhan D, Zeng Q (2012) Chem Comm 48:5367
Zeng Q, Weng W, Xue X (2012) Inorg Chim Comm 388:11
Dong J, Li T, Lv X, Zhou L, Weng W, Zhang Y, Zeng Q (2013) Appl Organomet Chem 27:337
Wolfe JF, Rathman TL, Sleevi MC, Campbell JA, Greenwood TD (1990) J Med Chem 33:161
Dabiri M, Baghbanzadeh M, Delbari AS (2008) J Comb Chem 10:700
Dean WD, Papadopoulos EP (1982) J Heterocycl Chem 19:171
Lee ES, Son JK, Na YH, Jahng Y (2004) Heterocycl Commun 10:325
Bhat BA, Sahu DP (2004) Synth Commun 34:2169
Anthony SP (2012) Chem Asian J 7:374
Rostamizadeh S, Nojavan M, Isapoor E, Azad M, Aryan R (2013) J Mol Catal A Chem 374:102
Trashakhova TV, Nosova EV, Valova MS, Slepukhin PA, Lipunova GN, Charushin VN (2011) Russ J Org Chem 47:753
Zhang X, Ye D, Sun H, Guo D, Wang J, Huang H, Zhang X, Jiang H, Liu H (2009) Green Chem 11:1881
Bentabed-Ababsa G, Ely SCS, Lassagne F, Mongin F, Snegaroff K, Bentabed-Ababsa G, Derdour A, Nassar E, Perspicace E, Stephanie H (2009) Org Biomol Chem 7:4782
Acknowledgments
We appreciate Allan Kipruto Chelashawʼs help. We thank the National Natural Science Foundation of China (No. 21372034) and the cultivating program for excellent innovation team of Chengdu University of Technology for financial support.
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Qiu, D., Wang, Y., Lu, D. et al. Potassium hydroxide-promoted transition-metal-free synthesis of 4(3H)-quinazolinones. Monatsh Chem 146, 1343–1347 (2015). https://doi.org/10.1007/s00706-015-1434-7
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DOI: https://doi.org/10.1007/s00706-015-1434-7