Studies on the Reaction of Diimines with Thiourea: Synthesis and Solvent-Induced cis/trans-Isomerization of 1,3,5-Triazinane-2-thiones
Synthesis
DOI: 10.1055/s-0029-1216884
Abstract
The reaction of ,′-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 CDCl by NMR analysis.
According to the NMR studies, the -diastereoisomer
undergoes a solvent-induced /-isomerization process, producing
the -diastereoisomer in DMSO. The stereochemistry
of the -diastereoisomer was determined
by X-ray crystallographic analysis.
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© Georg Thieme Verlag Stuttgart ˙ New York
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