One-pot three component synthesis of 2-amino-4H-chromenes under green and high efficient conditions

Iranian Journal of Catalysis

مقاله 1، دوره 5، شماره 4، اسفند 2015، صفحه 297-303   

نوع مقاله: Articles

نویسندگان

Leila Moradi^{* 1}؛ Mina Zare²

¹Faculty of Chemistry, Department of Organic Chemistry, University of Kashan, P.O. Box 8731751167 Kashan, I. R. Iran.

²Faculty of Chemistry, Department of Organic Chemistry, University of Kashan, P.O. Box 87317-51167, Kashan, Iran.

چکیده

A simple, mild and high efficient procedure for one pot three component synthesis of 2-amino 4-H chromene derivatives was studied. The reaction was performed in water using aryl aldehydes, malononitrile and resorcinol, phloroglucinol or naphthole in the presence of N-methyl D-glucamine (Meglumine) as a green high efficient catalyst. The reaction was studied in thermal, microwave (MW) and ultrasonic (US) conditions. Obtained results show that meglumine, as a green catalyst, has high efficiency in all reaction conditions and the yield of products (in all cases) is high to excellent. Environment friendly solvent and catalyst, short reaction times and high yield products are the advantageous of presented research.

کلیدواژه‌ها

Chromenes؛ Meglumine؛ One-pot؛ Green Conditions؛ ultrasonic؛ Microwave

مراجع

[1] B.C. Das, S. Mohapatra, P.D. Campbell, S. Nayak, S.M. Mahalingam, T. Evans, Tetrahedron Lett. 51 (2010) 2567-2570.
[2] H.R. Shaterian, M. Arman, F. Rigi, J. Mol. Liq. 158 (2011) 145-150.
[3] J.M. Khurana, B. Nand, P. Saluja, Tetrahedron. 66 (2010) 5637-5641.
[4] H. Nagabhushana, S.S. Saundalkar, L. Muralidhar, B.M. Nagabhushana, C.R. Girija, D. Nagaraja, M.A. Pasha, V.P. Jayashankara, Chin. Chem. Lett. 22 (2011) 143-146.
[5] L. Moafi, S. Ahadi, A. Bazgir, Tetrahedron Lett. 51 (2010) 6270-6274.
[6] B. Mohtat, H. Djahaniani, I. Yavari, M.G. Dehbalaei, S.A. Jam, Chin. Chem. Lett. 22 (2011) 771-773.
[7] O.M. Singh, N.S. Devi, D.S. Thokchom, G.J. Sharma, Eur. J. Med. Chem. 45 (2010) 2250-2257.
[8] S. Song, L. Song, B. Dai, H. Yi, G. Jin, S. Zhu, M. Shao, Tetrahedron 64 (2008) 5728-5735.
[9] Y. Gao, D.M. Du, Tetrahedron: Asymmetry 23 (2012) 1343-1349.
[10] B.V. Subba Reddy, M. Ramana Reddy, G. Narasimhulu, J.S. Yadav, Tetrahedron Lett. 51 (2010) 5677-5679.
[11] R. Maggi, R. Ballini, G. Sartori, R. Sartorio, Tetrahedron Lett. 45 (2004) 2297-2299.
[12] J.S. Yadav, B.V. Subba Reddy, S.K. Biswas, S. Sengupta, Tetrahedron Lett. 50 (2009) 5798-5801.
[13] H. Eshghi, M. Bakavoli, J. Abedini-Torghabeh, M. Rahimizadeh, Chin. Chem. Lett. 23 (2012) 1153-1156.
[14] K. Takenaka, S.C. mohanta, M.L. Patil, C.V. Laxman, S. Takizawa, T. Suzuki, H. Sasai, Org. Lett. 12 (2011) 3480-3483.
[15] Y. Liu, J. Qian, S. Lou, J. Zhu, Z. Xu, J. Org. Chem. 75 (2010) 1309-1312.
[16] D. Rajguru, B.S. Keshwal, S. Jain, Chin. Chem. Lett. 24 (2013) 1033-1036.
[17] H.J. Wang, J. Lu, Z.H. Zhang, Monatsh. Chem. 141 (2010) 1107-1112.
[18] N. Ramireddy, S. Abbaraju, C.G. Zhao, Tetrahedron Lett. 52 (2011) 6792-6295.
[19] R.Y. Guo, Z.M. An, L.P. Mo, S.T. Yang, H.X. Liu, S.X. Wang, Z.H. Zhang, Tetrahedron 69 (2013) 9931-9938.
[20] R.Y. Guo, Z.M. An, L.P. Mo, R.Z. Wang, H.X. Liu, S.X. Wang, Z.H. Zhang, ACS Comb. Sci. 15 (2013) 557–563.
[21] A.M. ElAgrody, A.M. AlDies, A.M. Fouda, Eur. J. Chem. 5 (2014) 133-137.
[22] C.B. Sangani, N.M. Shah, M.P. Patel, R.G. Patel, J. Serb. Chem. Soc. 77 (2012) 1165-1174.
[23] S. Makarem, A.A. Mohammadi, A.R. Fakhari, Tetrahedron Lett. 49 (2008) 7194-7196.
[24] D.S Raghuvanshi, K.N Singh. Arkivoc (2010) 305-317.
[25] S. Khaksar, A. Rouhollahpour, S.M. Talesh, J. Fluorine Chem. 141 (2012) 11–15.
[26] M. Kidwai, Pure. Appl. Chem. 73 (2001) 147-151.
[27] R.L. Magara, P.B. Thorata, V.B. Jadhava, S.U. Tekalea, S.A. Dakea, B.R. Patil b, R.P. Pawara, J. Mol. Catal. A: Chem. 374–375 (2013) 118–124.
[28] A.M. El-Maghraby, Org. Chem. Int. (2014) Article ID 715091, 6 pp.
[29] M. Mirza-Aghayan, S. Nazmdeh, R. Boukherroub, M. Rahimifard, A.A. Tarlani, M. Abolghasemi-Malakshah, Synth. Commun. 43 (2013) 1499–1507.
[30] Z. Zhou, F. Yang, L. Wu, A. Zhang, Chem. Sci. Trans. 1 (2012) 57-60
[31] J. Albadi, A. Mansournezhad, M. Darvishi-Paduk. Chin. Chem. Lett. 24 (2013) 208–210.
[32] D. Kumar, V.B. Reddy, B.G. Mishra, R.K. Rana, M.N. Nadagoudac, R.S. Varma, Tetrahedron. 63 (2007) 3093-3097.
[33] S.R. Kale, S.S. Kahandal, A.S. Burange, M.B. Gawande, R.V. Jayaram, Catal. Sci. Technol. 3 (2013) 2050-2056.
[34] J. Safari, M. Heydarian, Z. Zarnegar, Arab. J. Chem. 27 (2013) 1878-1882.
[35] T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li, Ultrason. Sonochem. 11 (2004) 393-397.
[36] X.S. Wang, G.S. Yanga, G. Zhao, Tetrahedron 19 (2008) 709-711.