An efficient and convenient synthesis of quinazoline derivatives catalyzed by cyanuric chloride in water
الموضوعات : Iranian Journal of Catalysis
Mahshid Hossaini
1
(Department of Chemistry, the University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran.)
Reza Heydari
2
(Department of Chemistry, the University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran.)
Malek Taher Maghsoodlou
3
(Department of Chemistry, the University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran.)
الکلمات المفتاحية: Water, green chemistry, Aldehyde, Cyanuric Chloride, Organo-catalyst, Quinazoline,
ملخص المقالة :
In this work, an eco-friendly procedure for the preparation of 2,3-dihydroquinazoline-4(1H)-ones was developed by condensation reaction of benzylic and heterocyclic aldehydes with 2-aminobenzamide in the presence of catalytic amounts of cyanuric chloride (2,4,6-trichloro-1,3,5-triazin) as an available and inexpensive organo-catalyst under aqueous media as a green conditions. The new compounds characterized by IR, 1HNMR, 13CNMR, Mass spectrometry, and CHN elemental analysis. Excellent yield, clean reaction media, simple workup and easy purification are advantages of this methodology.
[1] S. Karamthulla, S. Pal, M.N. Khan, L.H. Choudhury, RSC Adv. 4 (2014) 37889–37899.
[2] S.A. Ahmadi, D. Ghazanfari, Iran. J. Catal. 3 (2013) 177-181.
[3] Y. Takaya, T. Chiba, M. Tanitsu, K. Murata, H.S. Kim, Y. Wataya, Y. Oshima, Parasitol. Int. 47 (1998) 380.
[4] S.M. Roopan, F.N. Khan, J.S. Jin, R.S. Kumar, Res. Chem. Intermed. 37 (2011) 919–927.
[5] P. Kung, M.D. Casper, K.L. Cook, L. Wilson-Lingardo, L.M. Risen, T.A. Vickers, R. Ranken, L.B. Blyn, J.R. Wyatt, P. Dan Cook, D.J. Ecker, J. Med. Chem. 42 (1999) 4705-4713.
[6] A. Dandia, R. Singh, P. Sarawgi, J. Fluor. Chem. 126 (2005) 307–312.
[7] M. Zappala, S. Grasso, N. Micale, G. Zuccala, F.S. Menniti, G. Ferreri, G. De Sarroc, C. De Michelid, Bioorg. Med. Chem. Lett. 13 (2003) 4427–4430.
[8] D.W. Wang, H.Y. Lin, R.J. Cao, S.G. Yang, Q. Chen, G.F. Hao, W.C. Yang, G.F. Yang, J. Agric. Food Chem. 62 (2014) 11786−11796.
[9] M. Rahman, I. Ling, N. Abdullah, R. Hashim, A, Hajra, RSC Adv. 5 (2015) 7755-7760.
[10] M.T. Maghsoodlou, N. Khorshidi, M.R. Mousavi, N. Hazeri, S.M. Habibi-K.horassani, Res. Chem. Intermed. 41 (2014) 7497-7508.
[11] M. Tajbakhsh, R. Hosseinzadeh, P. Rezaee, M. Tajbakhsh, Chin. J. Catal. 35 (2014) 58–65.
[12] M.A. Bodaghi Fard, A. Mobinikhaledi, M. Hamidinasab, Synth. React. Inorg. Met. Org. Chem. 44 (2014) 567–571.
[13] A. Bharathi, S.M. Roopan, A. Kajbafvala, R.D. Padmaja, M.S. Darsana, G.N. Kumari, Chin. Chem. Lett. 25 (2014) 324–326.
[14] J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding, W. Su, Tetrahedron Lett. 49 (2008) 3814–3818.
[15] J. Wu, X. Du, J. Ma, Y. Zhang, Q. Shi, L. Luo, B. Song, S. Yang, D. Hu, Green Chem. 16 (2014) 3210–3217.
[16] M. Abdollahi-Alibeik, E. Shabani, Chin. Chem. Lett. 22 (2011) 1163–1166.
[17] A. Moradi, R. Heydari, M.T. Maghsoodlou, Res. Chem. Intermed. 41 (2015) 7377-7392.
[18] E. Siddalingamurthy, K.M. Mahadevan, J.N. Masagalli, H. N. Harishkumar, Tetrahedron Lett. 54 (2013) 5591–5596.
[19] W. Lin Li, Q. Yan Luo, F. Lin Yan, Chin. Chem. Lett. 22 (2011) 811–814
[20] M. Shariat, M. Wahid Samsudin, Z. Zakaria, Chem. Cent. J. 7 (2013) 58-63.
[21] M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Catal. Commun. 8 (2007) 1595–1598.
[22] M. Sharma, S. Pandey, K. Chauhan, D. Sharma, B. Kumar, P.M.S. Chauhan, J. Org. Chem. 77 (2012) 929−937.
[23] K.H. Narasimhamurthy, S. Chandrappa, K.S. Sharath Kumar, K.B. Harsha, H. Ananda, K.S. Rangappa, RSC Adv. 4 (2014) 34479–34486.
[24] L.Y. Zeng, C. Cai, J. Heterocycl. Chem. 47 (2010) 1035-1039.
[25] L. Gao, H. Ji, L. Rong, D. Tang, Y. Zha, Y. Shi, S. Tu, J. Heterocycl. Chem. 48 (2011). 957-960.
[26] J. Chen, W. Su, H. Wu, M. Liub, C. Jin, Green Chem. 9 (2007) 972–975.
[27] M. Wang, T. Ting Zhang, Y. Liang, J. Jing Gao, Chin. Chem. Lett. 22 (2011) 1423–1426.
[28] A. Ghorbani-Choghamarani, M. Norouzi, J. Mol. Catal. A: Chem. 395 (2014) 172–179.
[29] H.R. Safaei, M. Shekouhy, S. Khademi, V. Rahmanian, M. Safaei, J. Ind. Eng. Chem. 20 (2013) 3019-3024.
[30] M. Desroses, M. Scobie, T. Helleday, New J. Chem. 37 (2013) 3595-3597.
