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Versatile 2‐aminothiazoles, building blocks for highly functionalised heterocycles
Author(s) -
Kaupp Gerd,
Amer Fathy A.,
Metwally Mohamed Abbas,
AbdelLatif Ehab
Publication year - 2003
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.5570400603
Subject(s) - chemistry , thiazole , chloroacetyl chloride , knoevenagel condensation , tautomer , methylene , acetic anhydride , ring (chemistry) , ethyl cyanoacetate , organic chemistry , medicinal chemistry , chloride , catalysis , malononitrile
The reactions of quantitatively available 4‐phenyl‐ and 4‐(4‐antipyrinyl)‐2‐aminothiazole [“4‐antipyrinyl‐” is used as a short‐term for “4‐(1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1‐H‐pyrazol‐4yl)‐”] with chloroacetyl chloride, acetic anhydride, ethyl cyanoacetate and carbon disulphide are reported. The products are transformed further by Knoevenagel condensations and coupling reactions with aromatic diazonium salts. The latter occur both at the thiazole ring and at the active methylene sites. The tautomerism of these products is studied on the basis of density functional theory calculations at the B3LYP/6‐31G* level.