Abstract
An efficient one-pot synthesis of fused thiazolopyridinone derivatives (5-amino-6,7-diphenyl-4,7-dihydro-3H-thiazolo[4,5-b]pyridin-2-ones) by four-component reaction of aldehyde, benzylcyanide, ammonium acetate and thiazolidine-2,4-dione in ionic liquid is reported. This protocol has the advantages of environmental friendliness, higher yields, less reaction time, and convenient operation. Also, optimization of the synthesized compounds has been done using Hyperchem 8.0.
References
(a) Cantello B C C, Cawthorne M A, Cottam G P, Duff P T, Haigh D, Hindley R M, Lister C A, Smith S A and Thurlby P L 1994 J. Med. Chem. 37 3977; (b) Reaven G M 1988 Diabetes 37 1595
(a) Chen C, Xu S, Wang W X, Ding Y M, Yu K H, Wang B and Chen X Y 2009 Arch. Med. Res. 40 79; (b) Cruz P D L, Diez-Barra E, Loupy A and Langa F 1996 Tetrahedron Lett. 37 1113; (c) Aronoff S, Rosenblatt S, Braithwaite S, Egan J W, Mathisen A L and Schneider R L 2000 Diabetes Care 23 1605
(a) Barnett D, Craig J G, Robinson D S and Rogers M P 1977 Br. J. Clin. Pharmacol. 4 455; (b) Berger J and Moller D E 2002 Annu. Rev. Med. 53 409; (c) Cantello B C, Cawthorne M A, Cottam G P, Duff P T, Haigh D, Hindley R M, Lister C A, Smith S A and Thurlby P L 1994 J. Med. Chem. 37 3977; (d) Cox S L 2006 Drugs Today (Barc) 42 139, Desvergne B and Wahli W 1999 Endocrinol. Rev. 20 649; (e) Devasthale P V, Chen S, Jeon Y, Qu F, Shao C, Wang W, Zhang H, Cap M, Farrelly D and Golla R 2005 J. Med. Chem. 48 2248; (f) Ibrahimi A, Teboul L, Gaillard D, Amri E Z, Ailhaud G, Young P, Cawthorne M A and Grimaldi P A 1994 Mol. Pharmacol. 46 1070
(a) Kersten J R, Toller W G, Gross E R, Pagel P S and Warltier D C 2000 Am. J. Physiol. Heart Circ. Physiol. 278 H1218; (b) Kletzien R F, Clarke S D and Ulrich R G 1992 Mol. Pharmacol. 41 393; (c) Lehmann J M, Moore L B, Smith-Oliver T A, Wilkison W O, Willson T M and Kliewer S A 1995 J. Biol. Chem. 270 12953; (d) Ljung B, Bamberg K, Dahllof B, Kjellstedt A, Oakes N D, Ostling J, Svensson L and Camejo G 2002 J. Lipid Res. 43 1855; (e) Sohda T, Momose Y, Meguro K, Kawamatsu Y, Sugiyama Y and Ikeda H 1990 Arzneimittelforschung 40 37; (f) Yajima K, Hirose H, Fujita H, Seto Y, Fujita H, Ukeda K, Miyashita K, Kawai T, Yamamoto Y, Ogawa T, Yamada T and Saruta T 2003 Am. J. Physiol. Endocrinol. Metabol. 284 E966; (g) Yoshioka T, Fujita T, Kanai T, Aizawa Y, Kurumada T, Hasegawa K and Horikoshi H 1989 J. Med. Chem. 32 421
(a) Bienayme H, Hulme C, Oddon G and Schmitt P 2000 Chem. Eur. J. 6 3321; (b) Tietze L F and Modi A 2000 Med. Res. Rev. 20 304; (c) Deomling A and Ugi I 2000 Angew. Chem. Int. Ed. 39 3168; (d) Zhu J 2003 Eur. J. Org. Chem. 1133; (e) Orru R V A and de Greef M 2003 Synthesis 1471; (f) Nair V, Rajesh C, Vinod A U, Bindu S, Sreekanth A R, Mathen J S and Balagopal L 2003 Acc. Chem. Res. 36 899; (g) Simon C, Constantieux T and Rodriguez J 2004 Eur. J. Org. Chem. 4957
(a) Yuan Y, Li X and Ding K 2002 Org. Lett. 4 3309; (b) Cheng J F, Chen M, Arrhenius T and Nadzen A 2002 Tetrahedron Lett. 43 6293; (c) Huma H Z S, Halder R, Kalra S S, Das J and Iqbal J 2002 Tetrahedron Lett. 43 6485; (d) Bora U, Saikia A and Boruah R C 2003 Org. Lett. 5 435; (e) Dallinger D, Gorobets N Y and Kappe C O 2003 Org. Lett. 5 1205
(a) Hardy C R 1984 Adv. Heterocycl. Chem. 36 343; (b) Orth R E 1968 J. Pharm. Sci. 57 537; (c) Elnagdi M H, Elmoghayar M R H and Elgemeie G E H 1987 Adv. Heterocycl. Chem. 41 319; (d) Elnagdi M H, Elmoghayar M R H and Sadek K U 1990 Adv. Heterocycl. Chem. 48 223; (e) Liu X H, Cui P, Song B A, Bhadury P S, Zhu H L and Wang S F 2008 Bioorg. Med. Chem. 16 4075; (f) Palaska E, Aytemir M, Uzbay T and Erol D 2001 Eur. J. Med. Chem. 36 539; (g) Kees K L, Fitzgerald J J, Steiner K E Jr, Mattes J F, Mihan B, Tosi T, Mondoro D and McCaleb M L J 1996 Med. Chem. 39 3920
(a) Singh P, Katyal A, Kalra R and Chandra R 2008 Tet. Lett. 42, 727; (b) Singh P, Katyal A, Kalra R and Chandra R 2009 Spectro. Chim. Acta A 73, 218; (c) Kumari K, Singh P, Srivastava R C, Kumar P, Mehrotra G K, Samim M, Chandra R and Mordhwaj 2011 CPHEE Perspectives 69, 329; (d) Singh P, Kumari K, Dubey M, Vishwakarma V K, Pandey N D, Chandra R and Mehrotro G K 2012 Competes rendus- Chimie 15, 504; (e) Kumari K, Singh P, Dubey M, Pandey N D, Chandra R and Mehrotro G K 2012 Competes rendus-Chimie 15 267; (f) Singh P, Kumar P, Kumari K, Sharma P, Mozumdar S and Chandra R 2011 Spect. Acta A: Mol. Biomol. Spect. 78 909; (g) Singh P, Kumari K, Katyal A, Kalra R and Chandra R 2009 Cat. Lett. 127, 119; (h) Singh P, Kumari K, Katyal A, Kalra R and Chandra R 2009 Cat. Lett. 130, 648; (i) Singh P, Kumar S, Katyal A, Kalra R and Chandra R 2008 Mat. Lett. 62, 4164; (j) Singh P, Katyal A, Kalra R and Chandra R 2008 Cat. Commun. 9, 1618
(a) Dzyuba S V and Bartsch R 2003 Angew. Chem. Int. Ed. 42 148; (b) Wilker J S 2002 Green Chem. 4 73 (10) (c) Welton T 1999 Chem. Rev. 99 2071; (d) Dupont J, de Souza R F and Suarez P A Z 2002 Chem. Rev. 102 3667
(a) Fischer T, Sethi A, Welton T and Woolf J 1999 Tetrahedron Lett. 40 793; (b) Lee C W 1999 Tetrahedron Lett. 40 2461; (c) Ludley P and Karodia N 2001 Tetrahedron Lett. 42 2011; (d) Carmichael A J, Earle M J, Holbrey J D, McCormac P B and Seddon K R 1999 Org. Lett. 1, 997; (e) Calo V, Nacci A, Lopez L and Mannarini N 2000 Tetrahedron Lett. 41 8973
Acknowledgements
Authors thank the University Grant Commission (UGC) and the Department of Science and Technology (DST), New Delhi, India.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Rights and permissions
About this article
Cite this article
SINGH, P., KUMARI, K., KAITHWAS, G. et al. Efficient one-pot four-component synthesis of fused thiazolopyridin-2-ones in ionic liquid. J Chem Sci 125, 1471–1480 (2013). https://doi.org/10.1007/s12039-013-0522-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-013-0522-7