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

✍ Scribed by Srinivas Banala; Klaus Wurst; Bernhard Kräutler

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: German
• Weight: 182 KB
• Volume: 93
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200900362

✦ Synopsis

Abstract

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‐2__H__‐thieno[2,3‐c]pyrrole 1,1‐dioxide (‘β′‐sulfolenopyrrole’) from the expected cyclocondensation. A serendipitous formation of this β′‐sulfolenopyrrole was found earlier, when we investigated synthetic routes to a 3,5‐dihydro‐1__H__‐thieno[3,4‐c]pyrrole 2,2‐dioxide (a ‘β″‐sulfolenopyrrole’) from TsMIC and 2,5‐dihydrothiophene 1,1‐dioxide (‘3‐sulfolene’). Here, we present the synthesis and characterization of β′‐sulfolenopyrrole. The X‐ray crystal‐structure analyses of β′‐sulfolenopyrrole and the isomeric β″‐sulfolenopyrrole are also reported here. This β′‐sulfolenopyrrole is a new type of a functionalized pyrrole, which is likely to be of interest for pharmaceutical purposes.