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Synthesis of thiocarbonyl and heterocyclic compounds from 2‐methylene‐1,3‐dithietanes
Author(s) -
Okajima Nobuyuki,
Okada Yoshiyuki
Publication year - 1990
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.5570270317
Subject(s) - chemistry , methylene , reagent , yield (engineering) , ring (chemistry) , carbon atom , medicinal chemistry , thiadiazoles , organic chemistry , materials science , metallurgy
2‐Methyl‐1,3‐dithietanes bearing electron withdrawing groups on the methylene carbon atom were synthesized and their reactivities were studied. These compounds readily underwent a ring‐opening reaction with a variety of nucleophic reagents such as amines, alcoholate and thiolate anions to yield thioamides, thionoesters and dithioesters, respectively. The products were applied for synthesis of heterocycles such as thiadiazoles, isothiazolones and pyrazoles.