Novel procedure for preparation of Hantzsch 1, 4- dihydropyridines using PEG-400 as a reaction medium and under catalyst-free condition

Subject Areas :

Ali Ezabadi ¹ (Department of Chemistry, Faculty of Sciences, Islamic Azad University, Central Tehran Branch, Sanat Square, Iran)
Fatemeh Tosan ² (Department of Chemistry, Faculty of Sciences, Islamic Azad University, Central Tehran Branch, Sanat Square, Iran)

Received: 2015-07-10 Accepted : 2015-10-10 Published : 2015-12-01

Keywords: Hantzsch 1, 4 – dihydropyridines, PEG-400, Three-component reaction, catalyst-free, Aldehydes, ethyl acetoacetate, ammonium acetate,

Abstract :

An efficient and expeditious catalyst-free procedure was developed for the one- pot synthesis of 1, 4-dihydropyridine derivatives via the three-component reaction of various aldehydes, ethyl acetoacetate, and ammonium acetate in PEG-400. The reaction was carried out at 110°С and the products were obtained in good to high yields.

References:

[1] Caneias, N.R., Branco, L.C.Gois, P.M.P.Afonso, C.A.M.Trindade, A.F. Chem. Rev., 109, 2703, (2009).

[2] (a) A.Saunsins, G.Duburs, Hetrocycles. 1988, 27, 269; (b) R.H.Bocker, F.P.Guen.Guerich, J.Med.Chem. 1986, 28 1956; (c) T.Godfraid, R.Miller, M.wibo, Pharmacol.Rev.1986, 38, 321; (d) P.P.Mager, R.A.Coburn, A.J.Solo, D.J.Triggle, H.Rothe, Drug Des Discovery. 1992, 8 , 273; (e) R.Mannhold, B.Jablonca, W.Voigdt, K.Schoenafinger, Eur.J.Med.Chem. 1992,289.

        [3] (a) F.Bossert, H.Meyer, H.Wehinger, Angew.Chem., Int.Ed.Engl. ,1981, 20 , 762;                                                           (b)H.Nakayama, Y.Kasoaka, Heterocycles. 1996, 42 ,901; (c) M.F.Gordeev, D.V.Patel, E.M.Gordon, J.Org.Chem.1996,26 , 924; (d) F.R.Buhler, W.J.Kiowski, J.Hypertens, 1987,15 , S3; (e) J.L.Reid, P.A.Meredith, F.J.Pasanisi, J.Cardiovasc, Pharmacol. 1985, 7 ,S18; (f) Y.Sawada, H.Kayakiri, Y.Abe, T.Mizutani, N.Inamura, M.Asano, C.Hatori,  I.Aramor, T.Oku, H.Tanak, J.Med.Chem. 2004,  47 , 2853; (g) R.Shan, C.Velaskez, E.E.Knaus, J.Med.Chem. 2004, 47 , 321; (h) R.Miri, K.Javidnia, H.Sarkarzadeh, B.Hemmateenejad, Bio org.Med.Chem.Lett. 2006, 14 ,4842.

         [4] T.Itioh, K.Nagata, M.Miyazaki, H.Ishikawa, A.Kurihara, A.Ohsawa, Tetrahedron, 2004,60 , 6649.

        [5] (a) K.Akagawa, H.Akabane, S.Sakamoto, K.Kazuaki, Org.Lett. 10 (2008) 2035; (b) Q.Kang, Z.A.Zhao, S.L.You, Org.Lett. 2008,10 , 2031.

        [6] J.Baskove, D.Bevk, B.Stanovnik, J.Svete, J.Comb.Chem. 2009, 11 , 500 and references cited there.

        [7] I.Loev, K.M.Snader, J.Org.Chem. 1965,  30 , 1914.

        [8] (a) B.M.Khadikar, V.G.Gaikar, A.A.Chitnavis, Tetrahedron Lett. 1995, 36 , 8083; (b) L.Ohbery, J.Westman, Synlett. 2001,1296.

        [9] (a) S.J.Ji, Z.Q.Jiang, J.Lu, Y.P.Loh, Synlett. 2004, 831; (b) R.Sridhar, P.T.Perumal, Tetrahedron. 2005,61 , 2465.                                                        

        [10] G.Sabitha, K.Arundhathi, K.Sudhakar, B.S.Sastry, J.S.Yadav, Synth.Commun. 2009,39 , 2843.

        [11] S.D.Sharma, P.Hazorika, D.Konwar, Cat.Commun. 2008,  9 , 709.

        [12] Suresh, D.Kumar, J.S.Sandhu, Synth.Commun. 2009, 39 , 1957.

        [13] M.Maheswara, V.Siddaiah, Y.K.Rao, Y.M.Tzeng, C.Sridhar, J.Mol.Cat.A:Chemical. 2006,26 , 179.

        [14] M.A.Chari, K.Syamasunndor, Cat.Commun. 2005,  6 , 624.

        [15] H.Adibi, H.A.Samimi, M.Beygzadeh, Cat.Commun. 2007, 8 , 2119.

        [16] A.Debache, R.Boulcina, A.Belfaitah, S.Rhouati, B.Carboni.Synlett. 2008, 4 , 509.

        [17] E.Rafiee, S.Eavani, S.Rashidzadeh, M.Joshaghani, Inorganica Chimica Acta. 2009,  36 , 3555.

       [18] A.M.Zonouz, S.B.Hosseini, Synth.Commun. 2008, 38 ,290.

        [19] G.Sabitha, G.S.K.Reddy, C.S.Reddy, J.S.Yadav, Tetrahedron Lett. 2003, 44 , 4129.

        [20] J.Chen, S.K.Spear, J.G.Huddleston, R.D.Rogers, Green Chem. 2005, 7 , 64.

        [21] (a)J.Liang, J.Lv, J.C.Fan, Z.C.Shang, Synth.Commun. 2009,  39 , 2822; (b) D.Zhu, J.Chen, H.Xia, M.Liu, J.Ding, H.Wu, Synth.Commun. 2009,39 , 2895; (c) W.Han, C.Liu, Z.L.Jin, Org.lett. 2007, 9 , 4005; (d) F.N.Victoria, C.S.Radatz, M.Sachini, R.G.Jacob, G.Perin,W.P.D.Silva, E.J.Lenardao, Tetrahedron Lett. 2009, 50 , 6761; (e) V.V.Kouznestov, D.R.M.Areans, A.R.R.Bohorquez, Tetrahedron Lett. 2008, 49 , 3097; (f) A.R.Kiasat, R.Badri, B.Zargar, S.Sayyahi, J.Org.Chem. 2008,73 ,8382; (g) C.Mukhopadhyay, P.K.Tapaswi, Tetrahedron Lett. 2008, 49 , 6237; (h) M.A.Kumar, M.F.S.Babu, K.Srinvasulu, Y.P.Kiran, C.S.Reddy, J.Mol.Catal.A:Chem. 2007, 265 ,267; (i) Y. Q.Cao, Z.Zhang, Y.X.Guo, G.Q.Wu ,Synth.Commun. 2008,  38 , 1325; (j) S.Chandrasekhar, C.Narsihmulu, S.S.Sultana, N.R.Reddy, Org.lett. 2002,  4 , 4399; (k) S.Chandrasekhar, S.J.Prakash, C.L.Rao, J.Org.Chem. 2006, 71 ,2196; (l) P.Ferreira, E.Phillips, D.Rippon, S.C.Tsang, W.Hayes, J.Org.Chem. 2004,69 , 6851; (m) B.Sauvagnat, F.Lamaty, R.Lazaro,J.Martinez, Tetrahedron Lett. 2000, 41 ,6371; (n) R.Ballini, L.Barboni, A.Paimieri, Green Chem. 2008,10,1004; (o) S.L.Jain, S.Singhal, B.Sain, Green Chem.2007,9 ,740; (p) S.Chandrasekhar, C.Narsihmulu, S.S.Sultana, N.R.Reddy, Chem.Commun. 2003, 1716; (q) Z.H.Zhang, L.Yin, Y.M.Wang,   J.Y.Liu, Y.Li, Green Chem. 2004,6 , 563; (r) Y.R.Jorapur, G.R.Rajagopal, P.J.Saikia, R.R.Pal, Tetrahedron Lett. 49 (2008) 1495; (s) X.C.Wang, H.P.Gong, Z.J.Quan, L.Li,H.L.Ye, Chinese Chem.Lett. 2009,20 , 44; (t) K.Venkateswarlu, K.Suneel, B.Das, K.N.Reddy, T.S.Reddy, Synth.Commun.2009,39 , 215;  (u) Y.Q.Cao, Z.Dai, R.Zhang, B.H.Chen, Synth.Commun. 2005, 35 ,1045; (v) R.Kumar, P.Chaudhary, S.Nimesh, R.Chandra,Green Chem. 2006, 8 , 356.