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Benzothiazinones by addition of o ‐Mercaptobenzamides to acetylene esters
Author(s) -
Heindel Ned D.,
Ko C. C. Ho
Publication year - 1970
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.5570070502
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , acetylene , yield (engineering) , alkyne , sulfide , ring (chemistry) , medicinal chemistry , adduct , condensation , organic chemistry , catalysis , cycloaddition , materials science , physics , metallurgy , thermodynamics
The condensation of o ‐mercaptobenzamides with methyl acetylenedicarboxylate or methyl propiolate occurs with trans addition of the SH to the alkyne linkage. The resulting vinyl sulfide adducts can be ring closed to 1,3‐benzothiazin‐4‐ones in excellent yield.