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Thermolysis of N,N ″‐1,ω‐alkanediyl‐bis[n′‐organylthiourea] derivatives
Author(s) -
Hassan Alaa A.,
Döupp Dietrich
Publication year - 2006
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.5570430311
Subject(s) - chemistry , thermal decomposition , intramolecular force , medicinal chemistry , decomposition , stereochemistry , organic chemistry
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.