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Synthesis 2009(18): 3089-3093  
DOI: 10.1055/s-0029-1216884
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Studies on the Reaction of Diimines with Thiourea: Synthesis and Solvent-Induced cis/trans-Isomerization of 1,3,5-Triazinane-2-thiones

Babak Kaboudin*a, Tahereh Ghasemia, Tsutomu Yokomatsub
a Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Gava Zang, Zanjan 45195-1159, Iran
Fax: +98(241)4249023; e-Mail: kaboudin@iasbs.ac.ir;
b School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horonouchi, Hachioji, Tokyo 192-0392, Japan
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Publication History

Received 29 April 2009
Publication Date:
01 July 2009 (online)

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Abstract

The reaction of N,N′-bis(arylmethylidene)arylmethane diimines with thiourea under reflux in methanol was studied. The reaction gave a diastereomeric mixture of 4,6-disubstituted 1,3,5-triazinane-2-thiones in good yields. Two diastereoisomers of 4,6-diphenyl-1,3,5-triazinane-2-thione were detected in a solution of CDCl3 by NMR analysis. According to the NMR studies, the cis-dia­stereoisomer undergoes a solvent-induced cis/trans-isomerization process, producing the trans-diastereoisomer in DMSO. The stereochemistry of the trans-diastereoisomer was determined by X-ray crystallographic analysis.

Key words

diimines - thiourea - 1,3,5-triazinanes - configurational isomerism

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