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Ring-Opening/Ring-Closing Protocols from Nitrothiophenes: Easy Access toN-Fused Pyrroles through a Tandem 1,6-H Shift/6π-Electrocyclization

Authors :
Massimo Maccagno
Lara Bianchi
Cinzia Tavani
Giovanni Petrillo
Carlo Scapolla
Alessandra Tirocco
Source :
European Journal of Organic Chemistry. 2014:39-43
Publication Year :
2013
Publisher :
Wiley, 2013.

Abstract

The ring opening of 3-nitro-4-(phenylsulfonyl)thiophene with amines and proper modification of the resulting 1,3-diene enables a simple and versatile approach to N-fused pyrroles of both synthetic and biological interest through 1,6-H shift followed by 6π 1,5-electrocyclization. This protocol is effectively driven to the isolated pyrroles by an easy aromatization.

Details

ISSN :
1434193X
Volume :
2014
Database :
OpenAIRE
Journal :
European Journal of Organic Chemistry
Accession number :
edsair.doi...........b9ca641f5634eee1ffc4f16243c29a3d