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Synthesis of Novel Disubstituted Pyrazolo[1,5‐ a ]pyrimidines, Imidazo[1,2‐ a ]pyrimidines, and Pyrimido[1,2‐ a ]benzimidazoles Containing Thioether and Aryl Moieties
Author(s) -
Li Gang,
Zhang ZunTing,
Dai LiYan,
Du YinLi,
Xue Dong
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100495
Subject(s) - sulfanyl , chemistry , thioether , amine gas treating , aryl , medicinal chemistry , stereochemistry , mass spectrum , combinatorial chemistry , organic chemistry , ion , alkyl
A series of novel 6‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]‐7‐phenylpyrazolo[1,5‐ a ]pyrimidines, 5‐phenyl‐6‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]imidazo[1,2‐ a ]pyrimidines, and 2‐phenyl‐3‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]pyrimido[1,2‐ a ]benzimidazoles have been synthesized in four steps starting with 2‐hydroxyacetophenone. The intermediate 3‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]‐4 H ‐1‐benzopyran‐4‐ones reacted with pyrazol‐3‐amines, 5‐methylpyrazol‐3‐amine, and 1 H ‐imidazol‐2‐amine, 1 H ‐benzimidazol‐2‐amine via a cyclocondensation to give the title compounds in the presence of MeONa as base, respectively. The approach affords the target compounds in acceptable‐to‐good yields. The new compounds were characterized by their IR, NMR, and HR mass spectra.