Intramolecular Cyclization of 1-Benzyl-2-(nitromethylene)pyrrolidines in Triflic Acid

Abstract

1-Benzyl-2-(nitromethylene)pyrrolidines in triflic acid undergo intramolecular cyclization to afford the corresponding 2,3-dihydro-1H-pyrrolo[1,2-b]isoquinolinium triflates and/or 10-amino-2,3-dihydro-1H-pyrrolo[1,2-b]isoquinolinium triflates, depending on the nature of the aromatic substituent. Structures of products and reaction mechanisms are discussed.

GRAPHICAL ABSTRACT

Keywords:

• Intramolecular cyclization
• isoquinolinium triflates
• 2-(nitromethylene)pyrrolidines
• protonation
• triflic acid

Acknowledgments

This publication is dedicated in memory of Professor Jean-Marie Coustard, who supervised this work but passed away at the end of August 2013.