Synfacts 2007(10): 1035-1035  
DOI: 10.1055/s-2007-968978
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Thieno[3,2-b]thiophene 1,1-Dioxide Derivatives

Contributor(s): Victor Snieckus, Wei Gan
C. Fattuoni*, M. Usai, M. G. Cabiddu, E. Cadoni, S. De Montis, S. Cabiddu
UniversitÀ di Cagliari, Monserrato, Italy
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Publikationsverlauf

Publikationsdatum:
07. November 2007 (online)

Significance

A one-pot synthesis of 3-aryl- or heteroaryl-substituted thieno[3,2-b]thiophene di­oxide derivatives is reported. The reaction proceeds via an interesting bimetallation of 3-(methylsulfonyl)thiophene in which the α-sulfonyl anion appears to act, in view of no observed metallation at the comparably acidic C-5 site, as a directed metallation group. Subsequent quench with aryl or heteroaryl esters leads to the products. The starting materials are prepared by treatment of commercially available 3-(methylthio)thiophene with MCPBA. The scope of the reaction was meagerly investigated.