Triflic Acid Mediated Cyclization of Unsymmetrical N-Phenethyl- and N-(3-Indolylethyl)succinimides: Regio- and Diastereoselective Synthesis of Substituted Pyrroloisoquinolinones and Indolizino­indolones

Abstract The regio and diastereoselective synthesis of 1 or 2 alkyl-substituted pyrroloisoquinolinones and indolizinoindolones by triflic acid mediated cyclization via an electrophilic activation of unsymmetrical succinimide carbonyl groups followed by the reduction of fused cyclic N -acyliminium io...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2017-03, Vol.49 (5), p.1053-1064
Main Authors: Selvakumar, Jayaraman, Mangalaraj, Selvaraj, Achari, Kamsali Murali Mohan, Mukund, Krishna, Ramanathan, Chinnasamy Ramaraj
Format: Article
Language:English
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Summary:Abstract The regio and diastereoselective synthesis of 1 or 2 alkyl-substituted pyrroloisoquinolinones and indolizinoindolones by triflic acid mediated cyclization via an electrophilic activation of unsymmetrical succinimide carbonyl groups followed by the reduction of fused cyclic N -acyliminium ion is reported. This strategy successfully furnished the pyrroloisoquinolinone and indolizinoindolone derivatives in regio- and diastereoselective manner. The steric factor dictates the regioselectivity in N -phenethyl unsymmetrical succinimides and electronic factor seems to dictate the regioselectivity in N -(3-indolylethyl) unsymmetrical succinimides.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588639