3,5-Dihydro-2H-thieno[2,3-c]pyrrole 1,1-Dioxide - A New Simple Pyrrole Unit Preliminary Communication

作者：B****a Srinivas^*; Wurst Klaus; Kraeutler Bernhard

来源：Helvetica Chimica Acta, 2010, 93(6): 1192-1198.

DOI：10.1002/hlca.200900362

2,3-Dihydrothiophene 1,1-dioxide ('2-sulfolene') reacted with tosylmethyl isocyanide (TsMIC) in the presence of a base to give the hitherto unknown 3,5-dihydro-2H-thieno[2,3-c]pyrrole 1,1-dioxide ('beta'-sulfolenopyrrole') from the expected cyclocondensation. A serendipitous formation of this beta'-sulfolenopyrrole was found earlier, when we investigated synthetic routes to a 3,5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxide (a 'beta"-sulfolenopyrrole') from TsMIC and 2,5-dihydrothiophene-1,1-dioxide ('3-sulfolene'). Here, we present the synthesis and characterization of beta'-sulfolenopyrrole. The X-ray crystal-structure analyses of beta'-sulfolenopyrrole and the isomeric beta"-sulfolenopyrrole are also reported here. This beta'-sulfolenopyrrole is a new type of a functionalized pyrrole, which is likely to be of interest for pharmaceutical purposes.

• 出版日期2010