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Synthesis 2003(3): 0340-0342
DOI: 10.1055/s-2003-37340
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Annulation of the Thiete Ring on Imidazole Nucleus and LiI-Catalysed Expansion of the Thiete Ring with Carbon Disulfide

Lal Dhar S. Yadav*, Sarvesh Singh
Department of Chemistry, University of Allahabad, Allahabad 211 002, India
Fax: +91(532)545021; e-Mail: lds-yadav@hclinfinet.com;
Further Information

Publication History

Received 21 November 2002
Publication Date:
19 February 2003 (online)

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Abstract

One-pot annulation of 5-arylidene-2-thiohydantoins (3a-f) with O,O-diethyl hydrogen dithiophosphate (4) yields 3,5-dihydrothieto[2,3-d]imidazole-2(1H)-thiones (6a-f) which undergo LiI-catalysed facile expansion of their thiete ring with carbon disulfide to afford the corresponding dihydro[1,3]dithiino[4,5-d]imidazole-2,5(1H)-dithiones (7a-f).

Key words

conjugate addition - thieto-imidazoles - LiI-catalysed - ring expansion - [1,3]-dithiino-imidazoles