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Synthesis of new functionalized imidazo[2,1‐ b ]thiazoles and thiazolo[3,2‐ a ]pyrimidines
Author(s) -
PeterlinMašič Lucija,
Malešič Mateja,
Breznik Matej,
Krbavčič AleŠ
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370115
Subject(s) - chemistry , thiazole , formamide , oxalyl chloride , amide , pyrimidine , chirality (physics) , medicinal chemistry , carboxylic acid , stereochemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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 C5N6′ bond rotation were proved.