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

Chad E. Stephens, J. Walter Sowell

Research output: Contribution to journalArticle

5 Citations (Scopus)

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- 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.

Original languageEnglish (US)
Pages (from-to)191-192
Number of pages2
JournalJournal of Heterocyclic Chemistry
Volume37
Issue number1
DOIs
StatePublished - Jan 1 2000

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Thiadiazines
Thiadiazoles
Carboxylic Acids
Hydrolysis
Esters
Decomposition

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "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",
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- 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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T1 - 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

AU - Stephens, Chad E.

AU - Sowell, J. Walter

PY - 2000/1/1

Y1 - 2000/1/1

N2 - 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- 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.

AB - 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- 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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U2 - 10.1002/jhet.5570370133

DO - 10.1002/jhet.5570370133

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JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

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