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Reactions of Benzoyl Isothiocyanate with Active Methylene Reagents: A Novel Synthesis of Thiophene, Thiazoline and Thieno[2,3‐ d ]Pyrimidine Derivatives
Author(s) -
Mohareb Rafat Milad,
Aziz Suzan Ibrahim,
Saved Nadia Iskander Abdel,
Shams Hoda Zaki
Publication year - 1992
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199200030
Subject(s) - chemistry , phenacyl bromide , methylene , thiazoline , reagent , ethyl chloroacetate , potassium hydroxide , isothiocyanate , thiophene , phenyl isothiocyanate , pyrimidine , medicinal chemistry , bromide , organic chemistry , stereochemistry , hydrate
Various derivatives of thiophene, thiazoline and thienopyrimidine have been synthesized via the reaction of active methylene reagents (la‐j) with benzoyl isothiocyanate in the presence of potassium hydroxide, followed by the subsequent treatment of the potassium salt intermediates 2a‐j with phenacyl bromide or ethyl chloroacetate. The stability of the formed adducts 3 and 12 or their selective cyclization depends on both the nature of the active methylene reagent and the α‐halocarbonyl compounds.