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The synthesis of β‐heteroarylamino‐α,β‐dehydro‐α‐amino acid derivatives via thiazolones
Author(s) -
Smodiŝ Janez,
Stanovnik Branko,
Tiŝler Miha
Publication year - 1994
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.5570310133
Subject(s) - chemistry , sodium borohydride , sodium methoxide , methanol , ammonia , ethanol , derivative (finance) , nucleophile , medicinal chemistry , organic chemistry , sodium , catalysis , financial economics , economics
2‐Alkoxy‐4‐heteroarylaminomethylene‐5(4 H )‐thiazolones 4 were converted with various nucleophiles into β‐heteroarylamino‐α,β‐dehydro‐α‐amino acid derivatives 11, 14, 15, 16, 17, 18 , and 19 . Reduction of 4 with sodium borohydride in ethanol saturated with gaseous ammonia afforded the corresponding β‐heteroaryl‐amino substituted alanyl amides 20 . Thiazoledione derivative 7a was transformed with sodium methoxide in methanol into 1‐(4,6‐dimethylpyrimidinyl‐2)‐4‐mercaptocarbonylimidazol‐2(3 H )‐one ( 8a ).