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An interesting synthesis of thieno[2,3‐ d ][1,2,3]thiadiazole via decomposition/recyclization of 3‐methoxycarbonyl‐1 H ‐thieno‐[2,3‐ e ][1,3,4]thiadiazine 4,4‐dioxide
Author(s) -
Stephens Chad E.,
Sowell J. Walter
Publication year - 2000
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.5570370133
Subject(s) - chemistry , ring (chemistry) , decomposition , hydrolysis , medicinal chemistry , stereochemistry , organic chemistry
Attempted hydrolysis of the ester of 3‐methoxycarbonyl‐1 H ‐thieno[2,3‐ e ][1,3,4]thiadiazine 4,4‐dioxide ( I ) under acidic conditions gave the ring‐contracted thieno[2,3‐ d ][1,2,3]thiadiazole ( V ) instead of the expected carboxylic acid. In addition to a discussion of the reaction, a plausible mechanism is presented.
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