Thiamine hydrochloride (vitamin B1) as an efficient catalyst for the synthesis of 4-(3H)-Quinazolinone derivatives using grinding method.
محورهای موضوعی : Iranian Journal of CatalysisDeepak Kawade 1 , Mahendra Chaudhari 2 , Jitendra Gujar 3 , Murlidhar Shingare 4
1 - Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad - 431004, Maharashtra, India.
2 - Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad - 431004, Maharashtra, India.
3 - Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad - 431004, Maharashtra, India.
4 - Dr. Babasaheb Ambedkar Marthwada University, Aurangabad 431 004. (M.S.) (India)
کلید واژه: Multi-component reaction, Anthranilic acid, 4-(3H)-Quinazolinones, Thiamine hydrochloride (VB1),
چکیده مقاله :
Herein we explore facile synthesis of 4-(3H)-Qunazolinone derivatives, achieved by the cyclocondensation of anthranilic acid, aromatic amines and triethyl orthoformate in presence of thiamine hydrochloride (Vitamin B1) as a catalyst, using grinding method. This protocol offers several advantages such as reusability of catalyst, excellent yield, shorter reaction time and economic availability.Quinazolinone derivatives are one of the most important class of biodynamic heterocycles due to their wide range of biological activities such as anticancer [1], antitubercular agent [2], anti-inflammatory and antioxidant [3], anticonvusant agent [4], antimicrobial [5], antitumor [6], ACHE inhibitor [7], antiviral [8] and calcilytic activities [9-10]. Owing to the broad range of pharmacological, biological activities and development of new method for synthesis of quinazolinones derivative is still desirable.
[1] G.H. Zang, W.B. Xue, Y.F. Wang, F.Y. An, J.M. Yuan, J.K. Qin, C.X. pan, G.F. Su, Eur. J. Med. Chem. 95 (2015) 377-387.
[2] W. Lu, I.A. Baig, H.J. Sun, C.J. Cui, R. Guo, I. P. Jung, D. Wang, M. Dong, M.Y. Yoon, J.G. Wang, Eur. J. Med. Chem. 94 (2015) 298-305.
[3] K.P. Rakesh, H.M. Manukumar, D.C. Gowada, Bioorg. Med. Chem. Lett. 25 (2015) 1072-1077.
[4] H.S. A. Alsalem, G.H. Hegazy, K.E.H. El-Taher, S.M. El-Messery, A.M. Al-Obid, H.I. Subbagh, Bioorg. Med. Chem. Lett. 25 (2015) 1490-1499.
[5] D.R. Patel, K.C. Patel, J. Saudi Chem. Soc. 19 (2015) 347-359.
[6] R. Venkatesh, M.J. Ramaiah, H.K. Gaikawad, S. Janardhan, R. Bantu, L. Nagarapu, G.N. Sastry, A.R. Ganesh, M. Bhadra, Eur. J. Med. Chem. 94 (2015) 87-101.
[7] N.J. Liverton, D.J. Armstrong, D.A. Claremon, D.C. Remy, J.J Baldvin, R.J Lynch, G. Zhang, R.J. Gould, Bioorg. Med. Chem. 8 (1998) 483-486.
[8] J. Ma, P. Li, X. Li, Q. Shi, Z. Wan, D. Hu, L. Jin, B. Song, J. Agric. Food Chem. 62 (2014) 8928-8934.
[9] I. Shcherbakova, M.F. Balandrin, J. Fox, A. Ghatak, W.L. Heaton, R.L. Conklin, Bioorg. Med. Chem. Lett. 15 (2005) 1557-1560.
[10] S.L. Cao, Y.P. Feng, Y.-Y.Jiang, S.-Y. Liu, G.Y. Ding, R.T. Li, Bioorg. Med. Chem. Lett. 15 (2005) 1915-1917.
[11] G. Huang, B. Liu, M. Teng, Y. Chen, Synth. Commun. 44 (2014) 1786-1794.
[12] M. Narasimhulu, K.C. Mahesh, T.S. Reddy, K. Rajesh, Y. Venkateswarlu, Tetrahedron Lett. 47 (2006) 4381-4383.
[13] H.S. Wang, J.E. Zeng, Chin.J. Chem. 26 (2008) 175-178.
[14] M. Wang, Z.G. Song, T.T. Zhang, Monatsh. Chem. 141 (2010) 993-996.
[15] M. Wang, Z.G. Song, T.T. Zhang, Chem. Heterocycl. Compd. 46 (2010) 581-584.
[16] M. Wang, Z.G. Song, T.T. Zhang, Chin. Chem. Lett. 21 (2010) 1167-1170.
[17] X. B Jing, Z. Li, X. Pan, Y.C.A. Shi, J. Chin. Chem. Soc. 55 (2008) 1145-1149.
[18] M. Wang, Z. Song, T. Zhang, Synth. Commun. 41 (2011) 385-391.
[19] K. Ighilahriz, B. Boutemeur, F. Chami, C. Rabia, M. Hamdi, M.S. Hamdi, Molecules 13 (2008) 779-789.
[20] V.D. Dhakane, S.S. Gholap, U.P. Desmukh, H.V. Chavan, P.B. Bandgar, C.R. Chim. 17 (2014) 431-436.
[21] J. Liu, M. Lei, L. Hu, Green Chem. 14 (2012) 840-846.
[22] M. Lei, L. Ma, L. Hu, Synth. Commun. 41 (2011) 1969-1976.
[23] M. Lei, L. Ma, L. Hu, Tetrahedron Lett. 50 (2009) 6393-6393.
[24] M. Lei, L. Ma, L. Hu, Tetrahedron Lett. 51 (2010) 4186-4188.
[25] C. Nonnan, L. Bargawanath, S.L. Connan, Tetrahedron Lett. 49 (2008) 4003-4006.
[26] J. Sheenan, T. Hara, J. Org. Chem. 39 (1974) 1196-1999.
[27] G. Kaupp, Top. Curr. Chem. 254 (2005) 95-183.
[28] B. Rodrıguez, A. Bruckmann, T. Rantanen, C. Bolmvol, Adv. Syn. Catal. 349 (2007) 2213-2233.
[29] A. Bruckmann, A. Krebs, C. Bolm, Green Chem. 10 (2008) 1131-1141.
[30] K. Tanaka, S. Kishigami, F. Toda, J. Org. Chem. 56 (1991) 4333-4334.
[31] Z.J. Ren, W.G. Cao, W.Q. Tong, Synth. Commun. 32 (2002) 3475-3479
[32] G. Kaupp, M.R. Naimi-Jamal, J. Schmeyers, Tetrahedron 59 (2003) 3753-3760.
[33] C.L. Raston, J.L. Scott, Green Chem. 2 (2000) 49-52.
[34] D.A. Fulmer, W.C. Shearouse, S.T. Medonza, J. Mack, Green Chem. 11 (2009) 1821-1825.
[35] F. Toda, K. Tanaka, K. Hamai, J. Chem. Soc. Perkin Trans. 1 (1990) 3207-3209.
[36] M. Wang, Z.G. Song, T.T. Zhang, Org. Prep. Proc. Int. 42 (2010) 169-173.
