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Thermolysis of N,N″-1,ω-alkanediyl-bis[n′-organylthiourea] derivatives

✍ Scribed by Alaa A. Hassan; Dietrich Döupp

Book ID: 102345903
Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 400 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430311

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✦ Synopsis

Abstract

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The course of microwave assisted or conventional thermal intramolecular heterocyclization of the title compounds has been found to be dependent on the length of the alkanediyl chain. While 1,3‐propanediyl‐bisthioureas 5a‐c gave both 2‐thioxoperhydropyrimidine‐1‐carbothioamides 8a‐c and 8‐amino‐3,4,5,6‐tetrahydro‐1,3,7‐thiadiazocine‐2‐thiones 10a‐c, thermolysis of 1,4‐butanediyl‐bisthioureas 6a‐c and 1,6‐hexanediyl‐bisthioureas 7a‐c under the same conditions gave solely 9‐amino‐4,5,6,7‐tetrahydro‐1,3,8‐thiadiazonine‐2‐thiones 11a‐c and 11‐amino‐1‐thia‐3,10‐diazacycloundec‐10‐ene‐2‐thiones 12a‐c, respectively. Symmetric N,N′‐diorganylthioureas 4a‐c were formed in all cases as minor byproducts.

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