Download PDF
Synfacts 2007(9): 0916-0916  
DOI: 10.1055/s-2007-968912
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
Further Information

Publication History

Publication Date:
23 August 2007 (online)

    Permissions and Reprints

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 as a directed metallation group. Subsequent aryl or heteroaryl ester quench 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.