Synthesis of new functionalized imidazo[2,1-b]thiazoles and thiazolo[3,2-a]pyrimidines

✍ Scribed by Lucija Peterlin-Mašič; Mateja Malešič; Matej Breznik; AleŠ Krbavčič

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2000
• Tongue: English
• Weight: 523 KB
• Volume: 37
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570370115

✦ Synopsis

Abstract

5‐Oxo‐5__H__‐[1,3]thiazolo[3,2‐a]pyrimidine‐6‐carboxylic acid (4), and 6‐methylimidazo[2,1‐b]thiazole‐5‐carboxylic acid (17) were reacted with amines 6a‐i by the reaction with oxalyl chloride and N, N‐di methyl‐formamide as a catalyst into primary and secondary amide derivatives 7‐14 and 19‐22. From compound 24 N,N'‐disubstituted ureas 26, 27 and perhydroimidazo[1,5‐c]thiazole 29 derivatives of imidazo[2,1‐b]thiazole were prepared. By nmr analysis of compound 29, the existence of two stereoisomers resulting from both optical, due to centre of chirality at C7′a, and conformational isomerism, due to restricted C5N6′ bond rotation were proved.