Document Type: Short communication

Authors

1 Organic Chemistry Research laboratory, Department of Chemistry, Institute of Science, Nagpur-440001 Maharashtra, India.

2 School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Vishnupuri, Nanded-431606 Maharashtra, India.

3 Department of Chemistry, Institute of Science, Nagpur

Abstract

The highly substituted pyridine derivatives are found to exhibit diverse pharmacological activities. They are also emerged as potential medicinal leads in developing therapeutic agents for the treatment of various diseases. In this work, a series of 2-amino-3,5-dicarbonitrile-6-thio-pyridine derivatives have been synthesized at room temperature via one-pot, multi-component reaction of various aromatic aldehydes, malononitrile and thiophenols using catalytic amount of tetrabutylammonium bromide (TBAB) and cesium carbonate in methanol. In the present method, the use of thermal condition is avoided. In addition, the advantages such as operational simplicity, economic viability, ecologically benign nature make this protocol a very efficient alternative to the literature methods.

Graphical Abstract

Keywords

Main Subjects

[1]   a) R. Breslow, Acc. Chem. Res. 24 (1991) 159; (b) R. Breslow, Acc. Chem. Res. 37 (2004) 471.

[2]   S.B. Levy, M.N. Alekshun, B.L. Podlogar, K. Ohemeng, A.K. Verma, T. Warchol, B. Bhatia, T. Bowser, M. Grier, U.S. Patent Appl., 2005, 124, 678A1 20, 050, 609, 2005.

[3]   (a) T.R.K. Reddy, R. Mutter, W. Heal, K. Guo, V.J. Gillet, S. Pratt, B. Chen, J. Med. Chem. 49 (2006) 607; (b) B.C.H. May, J.A. Zorn, J. Witkop, J. Sherrill, A.C. Wallace, G. Legname, S.B. Prusiner, F.E. Cohen, J. Med. Chem. 50 (2007) 65.

[4]    H. Chen, W. Zhang, R. Tam, A.K. Raney, PCT Int. Appl. WO 2005058315 A1 20050630, 2005.

[5]    D.R. Anderson, N.W. Stehle, S.A. Kolodziej, E.J. Reinhard, PCT Int. Appl. WO 2004055015 A1 20040701, 2004.

[6]    H. Harada, S. Watanuki, T. Takuwa, K. Kawaguchi, T. Okazaki, Y. Hirano, C. Saitoh, PCT Int. Appl. WO 2002006237 A1 20020124, 2002.

[7]   (a) M.W. Beukers, L.C.W. Chang, J.K. Von FrijtagDrabbeKünzel, T. Mulder-Krieger, R.F. Spanjersberg, J. Brussee, A.P. Ijzerman, J. Med. Chem. 47 (2004) 3707; (b) L.C.W. Chang, J.K. Von FrijtagDrabbeKünzel, T. Mulder-Krieger, R.F. Spanjersberg, S.F. Roerink, G. Van Den Hout, M.W. Beukers, J. Brussee, A.P. Ijzerman, J. Med. Chem. 48 (2005) 2045; (c) U. Rosentreter, T. Kraemer, M. Shimada, W. Huebsch, N. Diedrichs, T. Krahn, K. Henninger, J.-P. Stasch, DE 10238113 A1 20030618, 2003; (d) U. Rosentreter, T. Kraemer, A. Vaupel, W. Huebsch, N. Diedrichs, T. Krahn, K. Dembowsky, J.-P. Stasch, M. Shimada, WO 2002079195 A1 20021010, 2002; (e) U. Rosentreter, T. Kraemer, A. Vaupel, W. Huebsch, N. Diedrichs, T. Krahn, K. Dembowsky, J.-P. Stasch, WO 2002070520 A1 20020912, 2002; (f) U. Rosentreter, T. Kraemer, A. Vaupel, W. Huebsch, N. Diedrichs, T. Krahn, K. Dembowsky, J.-P. Stasch, WO 2002070485 A1 20020912, 2002; (g) U. Rosentreter, R. Henning, M. Bauser, T. Kraemer, A. Vaupel, W. Huebsch, K. Dembowsky, O. Salcher-Schraufstaetter, J.-P. Stasch, T. Krahn, E. Perzborn, WO 2001025210 A2 2001041 2, 2001.

[8]  B.B. Fredholm, A.P. Ijzerman, K.A. Jacobson, K.-N. Klotz, J. Linden, Pharmacol. Rev. 53 (2001) 527.

[9]  K. Guo, R. Mutter, W. Heal, T.R.K. Reddy, H. Cope, S. Pratt, M.J. Thompson, B. Chen, Eur. J. Med. Chem. 43 (2008) 93.

[10] (a) M. Movassaghi, M.D. Hill, J. Am. Chem. Soc. 128 (2006) 4592; (b) A. Winter, N. Risch, Synthesis (2003) 2667.

[11] (a) M.D. Fletcher, T.E. Hurst, T.J. Miles, C.J. Moody, Tetrahedron 62 (2006) 5454; (b) K.J. Van Aken, G.M. Lux, G.G. Deroover, L. Meerpoel, G.J. Hoornaert, Tetrahedron 50 (1994) 5211.

[12]  A.D. Thomas, C.V. Asokan, Tetrahedron Lett. 43 (2002) 2273.

[13]   K. Tanaka, H. Mori, M. Yamamoto, S. Katsumara, J. Org. Chem. 66 (2001) 3099.

[14]   S.H. Mashraqui, M.A. Karnik, Tetrahedron Lett. 39 (1998) 4895.

[15]   A.R. Renslo, R.L. Danheiser, J. Org. Chem. 63 (1998) 7840.

[16]  (a) R.J. Vijn, H.J. Arts, R. Green, A.M. Castelijns, Synthesis (1994) 573. (b) S. Ahmed, R.C. Baruah, Tetrahedron Lett. 37 (1996) 8231.

[17]  M. Komatsu, H. Ohgishi, S. Takamatsu, Y. Ohshiro, T. Agawa, Angew. Chem., Int. Ed. Engl. 21 (1982) 213.

[18]  E.R. Anabha, K.N. Nirmala, A. Thomas, C.V. Asokan, Synthesis (2007) 428.

[19]  (a) N.M. Evdokimov, I.V. Magedov, A.S. Kireev, A. Kornienko, Org. Lett. 8 (2006) 899; (b) N.M. Evdokimov, A.S. Kireev, A.A. Yakovenko, M.Y. Antipin, I.V. Magedov, A. Kornienko, J. Org. Chem. 72 (2007) 3443.

[20]  B.C. Ranu, R. Jana, S. Sowmiah, J. Org. Chem. 72 (2007) 3152.                            

[21]  R. Mamgain, R. Singh, D.S. Rawat, J. Heterocycl. Chem. 46 (2009) 69.

[22]  K. Guo, M.J. Thompson, B. Chen, J. Org. Chem. 74 (2009) 6999.

[23]   M. Sridhar, B.C. Ramanaiah, C. Narsaiah, B. Mahesh, M. Kumarswamy, K.K.R. Mallu, V.M. Ankathi, P.S. Rao, Tetrahedron Lett. 50 (2009) 3897.

[24]   P.V. Shinde, S.S. Sonar, B.B. Shingate, M.S. Shingare, Tetrahedron Lett. 57 (2010) 1309.

[25]   K.N. Singh, S.K. Songh, ARKIVOC (xiii) (2009) 153.

[26]   N.M. Kantam, K. Mahender, S.J. Bhargava, Chem. Sci. 122(1) (2010) 63.

[27]    S. Banrjee, G. Sereda, Tetrahedron Lett. 50 (2009) 6959.

[28]    M.R.P. Heravi, F. Fakhr, Tetrahedron lett. 52 (2011) 6779.

[29]     S. Takale, J. Patil, V. Padalkar, R. Pisal, A. Chaskar, J. Braz. Chem. Soc. 23(5) (2012)  966.

[30]     A.K.B. Ahmed,H. Riaz, M. Keshari, Tetrahedron Lett. 50 (2009) 2889.

[31]     M.K. Jitender, S. Kumar, Tetrahedron Lett. 50 (2009) 4125.

[32]     G. Kurumurthy, G. Santosh Kumar, G. Malla Reddy, P. Nagender, P. Shanthan Rao, B. Narasaia, Res. Chem. Intermed. 38(2) (2012) 359.

[33]   (a) E.V. Dehmlow, S.S. Dehmlow, Phase Transfer Catalysis; 3rd ed.; VCH: Weinheim, 1993; (b) C.M. Starks, C.L. Liotta, M. Halpern, Phase-Transfer Catalysis: Chapman & Hall: New York, 1994; (c) Y. Sasson, R. Neumann, Handbook of Phase-Transfer Catalysis: Blackie Academic and Professiona, London, 1997; (d) M.E. Halpern, Phase Transfer Catalysis: ACS Symposium Series 659, American Chemical Society: Washington, DC, 1997; (e) M. Makosza, Pure Appl. Chem. 72 (2000) 1399.

[34]  (a) R. Chinchilla, L.R. Falvello, N. Galindo, C. Nájera, Angew. Chem. Int. Ed. Engl. 36 (1997) 995; (b) C. Nájera, T. Abellan, J.M. Sansano, Eur. J. Org. Chem. 65 (2000) 2809.

[35]   J. Lee, Y.-I. Lee, M.J. Kang, Y.-J. Lee, B.-S. Jeong, J.-H. Lee, M.-J. Kim, J. Choi, J.-M. Ku, H. Park, S. Jew, J. Org. Chem. 70 (2005) 4158.

[36]  T. Ooi, E. Tayama, K. Maruoka, Angew. Chem. Int. Ed. 42 (2003) 579.

[37]   D.Y. Kim, K.H. Suh, S.C. Huh, K. Lee, Synth. Commun. 31 (2001) 3315.

[38]   T. Weil, P.R. Schreiner, Eur. J. Org. Chem. 11 (2005) 2213.