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Synfacts 2008(8): 0806-0806  
DOI: 10.1055/s-2008-1077939
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Thiophenes and Annulated Thio-phenes via Alkylation of 3-Oxo-Propanedithioates

Contributor(s): Victor Snieckus, Erhad Ascic
R. Samuel, P. Chandran, S. Retnamma, K. A. Sasikala, N. K. Sreedevi, E. R. Anabha*, C. V. Asokan
Mahatma Gandhi University, Kottayam, India
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

Described is the de novo synthesis of polysubstituted thiophenes 5 and 6 by condensation of aryl 3-oxo-propanedithioates 1 and 2 with α-halo ketones which proceed via ketene dithioacetal intermediates 3 and 4 respectively. The cyclizations are limited to 3-oxo-propane­dithioates 1 with no α-substituents. The efficient acid- and base-catalyzed conditions for the conversions of 3 and 4 into the respective thiophenes 5 and 6 may be noted.