H3PW12O40 catalyzed synthesis of benzoxazine and quinazoline in aqueous media

doi:10.1016/S1872-2067(12)60706-2

摘要/Abstract

摘要：

A heteropolyacid efficiently catalyzed the cyclocondensation reaction of 2-aminobenzamide and salicylamide with aldehydes and ketones to afford good yields of benzoxazine and quinazoline ring systems in an aqueous medium. The method gives clean reactions, has simple workup procedure, and uses environment friendly conditions.

关键词: Heteropoly acid, 1,3-Benzoxazine-4-one, 2-Substituted-quinazolin-4(3H)-one, 2-Substituted-2,3-dihydroquinazolin-4(1H)-one

Abstract:

Key words: Heteropoly acid, 1,3-Benzoxazine-4-one, 2-Substituted-quinazolin-4(3H)-one, 2-Substituted-2,3-dihydroquinazolin-4(1H)-one

Mahmood Tajbakhsh, Rahman Hosseinzadeh, Parizad Rezaee, Mahgol Tajbakhsh. H₃PW₁₂O₄₀ catalyzed synthesis of benzoxazine and quinazoline in aqueous media[J]. 催化学报, 2014, 35(1): 58-65.

Mahmood Tajbakhsh, Rahman Hosseinzadeh, Parizad Rezaee, Mahgol Tajbakhsh. H₃PW₁₂O₄₀ catalyzed synthesis of benzoxazine and quinazoline in aqueous media[J]. Chinese Journal of Catalysis, 2014, 35(1): 58-65.

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参考文献

[1] Mizuno N, Misono M. Chem Rev, 1998, 98: 199
[2] Okuhara T, Mizuno N, Misono M. Adv Catal, 1996, 41: 113
[3] Kozhevnikov I V. Chem Rev, 1998, 98: 171
[4] Izumi Y, Hasebe R, Urabe K. J Catal, 1983, 84: 402
[5] Blasco T, Corma A, Martinez A, Martinez-Escolano P J. J Catal, 1998, 177: 306
[6] Kyle J H. J Chem Soc, Dalton Trans, 1983: 2609
[7] Dias A S, Pillinger M, Valente A A. Appl Catal A, 2005, 285: 126
[8] Keggin J F. Nature, 1933, 131: 908
[9] Misono M. Catal Rev-Sci Eng, 1987, 29: 269
[10] Kozhevnikov I V. Catal Rev-Sci Eng, 1995, 37: 311
[11] Pierce M E, Parsons R L Jr, Radesca L A, Lo Y S, Silvermon S, Moore J R, Islam Q, Chaodhury A, Fortunak J M D, Nguyen D, Luo C, Morgan S F, Davis W P, Confalone P N, Chen C, Tillyer R D, Frey L, Tan L, Xu F, Zhao D, Thompson A S, Corley E G, Grabowski E J J, Reamer R, Reider P J. J Org Chem, 1998, 63: 8536
[12] Kern J C, Terefenko E A, Fensome A, Unwalla R, Wrobel J, Zhu Y, Cohen J, Winneker R, Zhang Z, Zhang P. Bioorg Med Chem Lett, 2007, 17: 189
[13] Bolognese A, Correale G, Manfra M, Lavecchia A, Mazzoni O, Novellino E, Barone V, La Colla P, Loddo R. J Med Chem, 2002, 45: 5217
[14] Jarvest R L, Connor S C, Gorniak J G, Jennings L J, Serafinowska H T, West A. Bioorg Med Chem Lett, 1997, 7: 1733
[15] Hsieh P W, Hwang T L, Wu C C, Chang F R, Wang T W, Wu Y C. Bioorg Med Chem Lett, 2005, 15: 2786
[16] Waisser K, Gregor J, Kubicova L, Klimesova V, Kunes J, Machacek M, Kaustova J. Eur J Med Chem, 2000, 35: 733
[17] Hsieh P W, Chang F R, Chang C H, Cheng P W, Chiang L C, Zeng F L, Lin K H, Wu Y C. Bioorg Med Chem Lett, 2004, 14: 4751
[18] Fringuelli R, Pietrella D, Schiaffella F, Guarraci A, Perito S, Bistoni F, Vecchiarelli A. Bioorg Med Chem, 2002, 10: 1681
[19] Colson E, Wallach J, Hauteville M. Biochimie, 2005, 87: 223
[20] Atkinson P J, Bromidge S M, Duxon M S, Gaster L M, Hadley M S, Hammond B, Johnson C N, Middlemiss D N, North S E, Price G W, Rami H K, Riley G J, Scott C M, Shaw T E, Starr K R, Stemp G, Thewlis K M, Thomas D R, Thompson M, Vong A K K, Watson J M. Bioorg Med Chem Lett, 2005, 15: 737
[21] Afarinkia K, Bahar A, Neuss J, Ruggiero A. Tetrahedron Lett, 2004, 45: 3995
[22] Medaer B P, Hoornaert G J. Tetrahedon, 1999, 55: 3987
[23] Miyata O, Namba M, Ueda M, Naito T. Org Biomol Chem, 2004, 2: 1274
[24] Horrom B W, Zaugg H E. J Am Chem Soc, 1950, 72: 721
[25] Thienthong N, Perlmutter P. J Organomet Chem, 2005, 690: 2027
[26] Gammil R B. J Org Chem, 1981, 46: 3340
[27] Miyake T, Seki M, Nakamura Y, Ohmizu H. Tetrahedron Lett, 1996, 37: 3129
[28] Kondo K, Seki M, Kuroda T, Yamanaka T, Iwasaki T. J Org Chem, 1997, 62: 2877
[29] Madhavan G R, Chakrabarti R, Reddy K A, Rajesh B M, Balraju V, Rao P B, Rajagopalan R, Iqbal J. Bioorg Med Chem, 2006, 14: 584
[30] Vovk M V, Bol’but A V, Chernega A N. J Flourine Chem, 2002, 116: 97
[31] Vellalath S, Coric I, List B. Angew Chem Int Ed, 2010, 49: 9749
[32] Jiang J B, Hesson D P, Dusak B A, Dexter D L, Kang G L, Hamel E. J Med Chem, 1990, 33: 1721
[33] Farghaly A M, Soliman R, Khalil M A, Bekhit A A, El-Din A, Bekhit A. Boll Chim Farm, 2002, 141: 372
[34] Wolfe J F, Rathman T L, Sleevi M C, Campbell J A, Greenwood T D. J Med Chem, 1990, 33: 161
[35] Kurogi Y, Inoue Y, Tsutsumi K, Nakamura S, Nagao K, Yoshitsugu H, Tsuda Y. J Med Chem, 1996, 39: 1433
[36] Hour M J, Huang L J, Kuo S C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K H. J Med Chem, 2000, 43: 4479
[37] Lopez S E, Rosales M E, Urdaneta N, Godoy M V, Charris J E. J Chem Res, 2000, 2000: 258
[38] Armarego W L F. Adv Heterocycl Chem, 1979, 24: 1
[39] Segarra V, Crespo M I, Pujol F, Beleta J, Domenech T, Miralpeix M, Palacios J M, Castro A, Martinez A. Bioorg Med Chem Lett, 1998, 67: 5831
[40] Kamal A, Ramana K V, Ankati H B, Ramana A V. Tetrahedron Lett, 2002, 43: 6861
[41] Rao V B, Ratnam C V. Indian J Chem B, 1979, 18: 409
[42] Wang L M, Hu L, Shao J H, Yu J J, Zhang L. J Fluorine Chem, 2008, 129: 1139
[43] Mhaske S B, Argade N P. Tetrahedron, 2006, 62: 9787
[44] Naleway J J, Fox C M J, Robinhold D, Terpetschnig E, Olsen N A, Haugland R P. Tetrahedron Lett, 1994, 35: 8569
[45] Bhat B A, Sahu D P. Synth Commun, 2004, 34: 2169
[46] Abdel-Jalil R J, Voelter W, Saeed M. Tetrahedron Lett, 2004, 45: 3475
[47] Wang G W, Miao C B, Kang H. Bull Chem Soc Jpn, 2006, 79: 1426
[48] Potewar T M, Nadaf R N, Daniel T, Lahoti R J, Srinivasan K V. Synth Commun, 2005, 35: 231
[49] Bogert M T, Hand W F. J Am Chem Soc, 1902, 24: 1031
[50] Akazome M, Yamamoto J, Kondo T, Watanabe Y. J Organomet Chem, 1995, 494: 229
[51] Stephen H, Wadge G. J Chem Soc, 1956: 4420
[52] Takeuchi H, Hagiwara S, Eguchi S. Tetrahedron, 1989, 45: 6375
[53] Takeuchi H, Matsushita Y, Eguchi S. J Org Chem, 1991, 56: 1535
[54] Yang D S, Fu H, Hu L M, Jiang Y Y, Zhao Y F. J Comb Chem, 2009, 11: 653
[55] Alafeefy A M. J Saudi Chem Soc, 2011, 15: 337
[56] Wang B, Li Z, Wang X N, Tan J H, Gu L Q, Huang Z S. Chin Chem Lett, 2011, 22: 951
[57] Prakash M, Kesavan V. Org Lett, 2012, 14: 1896
[58] Kulkarni S S, Singh S, Shah J R, Low W K, Talele T T. Eur J Med Chem, 2012, 50: 264
[59] Jalani H B, Pandya A N, Pandya D H, Sharma J A, Sudarsanam V, Vasu K K. Tetrahedron Lett, 2012, 53: 4062
[60] Subba Reddy B V, Venkateswarlu A, Madan Ch, Vinu A. Tetrahedron Lett, 2011, 52: 1891
[61] Karimi-Jaberi Z, Arjmandi R. Monatsh Chem, 2011, 142: 631
[62] Liu J F, Lee J, Dalton A M, Bi G, Yu L, Baldino C M, McElory E, Brown M. Tetrahedron Lett, 2005, 46: 1241
[63] El-Helby A G A, Abdel-Wahab M H. Acta Pharm, 2003, 53: 127
[64] Jankowski F, Verones V, Flouquet N, Carato P, Berthelot P, Lebegue N. Tetrahedron, 2010, 66: 128
[65] Huang W, Huang R, Attene-Ramos M S, Sakamuru S, Englund E E, Inglese J, Austin C P, Xia M. Bioorg Med Chem Lett, 2011, 21: 5239
[66] Xu W, Jin Y B, Liu H X, Jiang Y Y, Fu H. Org Lett, 2011, 13: 1274
[67] Dabiri M, Salehi P, Otokesh S, Baghbanzadeh M, Kozehgary G, Mohammadi A A. Tetrahedron Lett, 2005, 46: 6123
[68] Chen J X, Wu D Z, He F, Liu M C, Wu H Y, Ding J C, Su W K. Tetrahedron Lett, 2008, 49: 3814
[69] Dabiri M, Salehi P, Baghbanzadeh M, Zolfigol M A, Agheb M, Heydari S. Catal Commun, 2008, 9: 785
[70] Dabiri M, Salehi P, Baghbanzadeh M. Monatsh Chem, 2007, 138: 1191
[71] Saffar-Teluri A, Bolouk S. Monatsh Chem, 2010, 141: 1113
[72] El-Sabbagh O I, Ibrahim S M, Baraka M M, Kothayer H. Arch Pharm, 2010, 343: 274
[73] Zhang Z H, Lü H Y, Yang S H, Gao J W. J Comb Chem, 2010, 12: 643
[74] Rao V B, Hanumanthu P, Ratnam C V. Indian J Chem B, 1979, 18: 493
[75] Gao L J, Ji H L, Rong L C, Tang D, Zha Y Y, Shi Y H, Tu S J. J Heterocycl Chem, 2011, 48: 957
[76] Song Z G, Liu L L, Wang Y, Sun X H. Res Chem Intermed, 2012, 38: 1091
[77] Dar B A, Sahu A K, Patidar P, Sharma P R, Mupparapu N, Vyas D, Maity S, Sharma M, Singh B. J Ind Eng Chem, 2013, 19: 407
[78] Sarrafi Y, Mehrasbi E, Vahid A, Tajbakhsh M. Chin J Catal (催化学报 ), 2012, 33: 1486
[79] Tajbakhsh M, Hosseinzadeh R, Alinezhad H, Rezaee P. Synth Commun, 2013, 43: 2370
[80] Montazeri N, Khaksar S, Nazari A, Alavi S S, Vahdat S M, Tajbakhsh M. J Fluorine Chem, 2011, 132: 450
[81] Bharate S B, Mupparapu N, Manda S, Bharate J B, Mudududdla R, Yadav R R, Vishwakarma R A. Arkivoc, 2012, (viii): 308
[82] Safaei H R, Shekouhy M, Shafiee V, Davoodi M. J Mol Liq, 2013, 180: 139
[83] Wang M, Zhang T T, Liang Y, Gao J J. Monatsh Chem, 2012, 143: 835
[84] Qiao R Z, Xu B L, Wang Y H. Chin Chem Lett, 2007, 18: 656
[85] Sharma M, Pandey S, Chauhan K, Sharma D, Kumar B, Chauhan P M S. J Org Chem, 2012, 77: 929
[86] Wang X S, Yang K, Zhou J, Tu S J. J Comb Chem, 2010, 12: 417Dabiri M, Mohammadi A A, Qaraat H. Monatsh Chem, 2009, 140: 401

H₃PW₁₂O₄₀ catalyzed synthesis of benzoxazine and quinazoline in aqueous media

H₃PW₁₂O₄₀ catalyzed synthesis of benzoxazine and quinazoline in aqueous media

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