An interesting synthesis of thieno[2,3-d][1,2,3]thiadiazole via decomposition/recyclization of 3-methoxycarbonyl-1H-thieno-[2,3-e][1,3,4]thiadiazine 4,4-dioxide

Authors
Stephens, CE Sowell, JW
Citation
Ce. Stephens et Jw. Sowell, An interesting synthesis of thieno[2,3-d][1,2,3]thiadiazole via decomposition/recyclization of 3-methoxycarbonyl-1H-thieno-[2,3-e][1,3,4]thiadiazine 4,4-dioxide, J HETERO CH, 37(1), 2000, pp. 191-192
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
37
Issue
1
Year of publication
2000
Pages
191 - 192
Database
ISI
SICI code
0022-152X(200001/02)37:1<191:AISOTV>2.0.ZU;2-5
Abstract
Attempted hydrolysis of the ester of 3-methoxycarbonyl-1H-thieno[2,3-e][1,3 ,4]thiadiazine 4,4-dioxide (I) under acidic conditions gave the ring-contra cted 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 i s presented.