A Novel Way to Tricyclic Heteroaromatics; Thiazolo[5,4-b]thieno[3,2-e]pyridine Derivatives

Abstract

Thiazolo[5,4-b]thieno[3,2-e]pyridine derivatives, novel tricyclic heteroaromatics, have been designed and synthesized by a one-pot reaction of diazepinethiones and aldehydes. This reaction is based on a novel rearrangement reaction of seven-membered 1,4-diazepine-2-thiones to six-membered 3-aminopyridine-2-thiols catalyzed by scandium(III) triflate.

Key words

rearrangement - cyclization - heterocycles - Lewis acid - catalysis

• References

• 1 These authors contributed equally.
• 2 Kaur J, Singh P. Expert Opin. Ther. Pat. 2011; 21: 437
• 3 Polshettiwar V, Varma RS. Pure Appl. Chem. 2008; 80: 777
• 4a Elliott TS, Slowey A, Ye Y, Conway SJ. Med. Chem. Commun. 2012; 3: 735
• 4b Brown N. Bioisosteres in Medicinal Chemistry . Wiley-VCH; Weinheim: 2012
• 4c Barnes MJ, Conroy R, Miller DJ, Mills JS, Montana JG, Pooni PK, Showell GA, Walsh LM, Warneck JB. H. Bioorg. Med. Chem. Lett. 2007; 17: 354
• 4d Kees KL, Caggiano TJ, Steiner KE, Fitzgerald JJ. Jr, Kates MJ, Christos TE, Kulishoff JM. Jr, Moore RD, McCaleb ML. J. Med. Chem. 1995; 38: 617
• 4e Thornber CW. Chem. Soc. Rev. 1979; 8: 563
• 5 Bongarzone S, Bolognesi ML. Expert Opin. Drug Discovery 2011; 6: 251
• 6 Di Modica G, Barni E. Gazz. Chim. Ital. 1963; 93: 679
• 7a Gonzalez-Sanchez I, Solano JD, Loza-Mejia MA, Olvera-Vazquez S, Rodriguez-Sotres R, Moran J, Lira-Rocha A, Cerbon MA. Eur. J. Med. Chem. 2011; 46: 2102
• 7b Loza-Mejia MA, Olvera-Vazquez S, Maldonado-Hernandez K, Guadarrama-Salgado T, Gonzalez-Sanchez I, Rodriguez-Hernandez F, Solano JD, Rodriguez-Sotres R, Lira-Rocha A. Bioorg. Med. Chem. 2009; 17: 3266
• 7c Loza-Mejia MA, Maldonado-Hernandez K, Rodriguez-Hernandez F, Rodriguez-Sotres R, Gonzalez-Sanchez I, Quintero A, Solano JD, Lira-Rocha A. Bioorg. Med. Chem. 2008; 16: 1142
• 7d Rodriguez-Loaiza P, Quintero A, Rodriguez-Sotres R, Solano JD, Lira-Rocha A. Eur. J. Med. Chem. 2004; 39: 5
• 7e Alvarez-Ibarra C, Fernandez-Granda R, Quiroga ML, Carbonell A, Cardenas F, Giralt E. J. Med. Chem. 1997; 40: 668
• 7f Bernstein SC, Abrams SK, Leckrone KJ, Paul LA. J. Pharm. Biomed. Anal. 1993; 11: 61
• 7g Moersdorf P, Schickaneder H, Engler H, Ahrens KH. DE 3533331, 1987
• 8a Reiser U, Ettmayer P, Kraemer O, Sennhenn P, Spevak W. WO 2007144370, 2007
• 8b Cullen E, Becker R, Freter K, LeClerq K, Possanza G, Wongt H.-C. J. Med. Chem. 1992; 35: 350
• 9a Cheng P, Zhang Q, Ma YB, Jiang ZY, Zhang XM, Zhang FX, Chen JJ. Bioorg. Med. Chem. Lett. 2008; 18: 3787
• 9b Ribeiro N, Tabaka H, Peluso J, Fetzer L, Nebigil C, Dumont S, Muller CD, Desaubry L. Bioorg. Med. Chem. Lett. 2007; 17: 5523
• 9c Chen P, Daugan AC.-M, Gosmini RL. M, Igo D, Katrincic L, Martres P, Nicodeme E, Patience D. WO 2006032470, 2006
• 9d Hewawasam P, Fan W, Knipe J, Moon SL, Boissard CG, Gribkoff VK, Starrett JE. Bioorg. Med. Chem. Lett. 2002; 12: 1779
• 10a Okano K, Miyazawa S, Clark RS. J, Abe S, Kawahara T, Shimomura N, Asano O, Yoshimura H, Miyamoto M. JP 03264588, 1991
• 10b Okano K, Miyazawa S, Clark RS. J, Abe S, Kawahara T, Shimomura N, Asano O, Yoshimura H, Miyamoto M, Sakuma Y, Muramoto K, Obaishi H, Harada K, Tsunoda H, Katayama S, Yamada K, Souda S, Machida Y, Katayama K. EP 0367110, 1990
• 10c Moriwaki M, Abe M, Mikashima H, Tahara T. WO 8809333, 1988
• 10d Nakanishi M, Araki K, Tahara T, Shiraki M. JP 49005357, 1974
• 10e Nakanishi M, Tahara T, Araki K, Shiroki M, Tsumagari T, Takigawa Y. J. Med. Chem. 1973; 16: 214
• 10f Nakanishi M, Araki K, Tahara T, Shiroki M. JP 48039491, 1973
• 10g Nakanishi M, Araki K, Tahara T, Shiroki M. DE 2107356, 1971
• 11a Kovač T, Belin B, Fajdiga T, Šunjić V. J. Heterocycl. Chem. 1981; 18: 59
• 11b Sternbach LH, Reeder E, Stempel A, Rachlin AI. J. Org. Chem. 1964; 29: 332
• 12a Kempen H, Bellus D, Staehelin B. WO 2010049466, 2010
• 12b Filippakopoulos P, Qi J, Picaud S, Shen Y, Smith WB, Fedorov O, Morse EM, Keates T, Hickman TT, Felletar I, Philpott M, Munro S, McKeown MR, Wang Y, Christie AL, West N, Cameron MJ, Schwartz B, Heightman TD, La Thangue N, French C, Wiest O, Kung AL, Knapp S, Bradner JE. Nature (London) 2010; 468: 1067
• 12c Kawakami Y, Kitani H, Yuasa S, Abe M, Moriwaki M, Kagoshima M, Terasawa M, Tahara T. Eur. J. Med. Chem. 1996; 31: 683
• 12d Miyazawa S, Okano K, Shimomura N, Clark RS. J, Kawahara T, Asano O, Yoshimura H, Miyamoto M, Sakuma Y. Chem. Pharm. Bull. 1991; 39: 3215
• 12e Polivka Z, Holubek J, Svatek E, Metys J, Protiva M. Collect. Czech. Chem. Commun. 1984; 49: 621
• 13a Miyazawa S, Okano K, Kawahara T, Machida Y, Yamatsu I. Chem. Pharm. Bull. 1992; 40: 762
• 13b Cava MP, Levinson MI. Tetrahedron 1985; 41: 5061
• 14 Xie J, Zhu X, Huang M, Meng F, Wang M, Wan Y. Synth. Commun. 2010; 40: 3259
• 15a Dhakshinamoorthy A, Alvaro M, Garcia H. Chem. Commun. 2010; 46: 6476
• 15b Fajkusova D, Pazdera P. Synthesis 2008; 1297
• 15c Bartolozzi A, Foudoulakis HM, Cole BM. Synthesis 2008; 2023
• 15d Chauhan SM. S, Kumar A, Srinivas KA. Chem. Commun. 2003; 2348
• 15e Sanz R, Aguado R, Pedrosa MR, Arnaiz FJ. Synthesis 2002; 856
• 16 Structural and other crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 989476 for compound 5a. A copy of the data can be obtained, free of charge, by applying to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: [phone] or e-mail: [e-mail]].