Synthesis 2017; 49(05): 1053-1064
DOI: 10.1055/s-0036-1588639
paper
© Georg Thieme Verlag Stuttgart · New York

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

Jayaraman Selvakumar
Department of Chemistry, Pondicherry University, Puducherry 605 014, India   Email: crrnath.che@pondiuni.edu.in
,
Selvaraj Mangalaraj
Department of Chemistry, Pondicherry University, Puducherry 605 014, India   Email: crrnath.che@pondiuni.edu.in
,
Kamsali Murali Mohan Achari
Department of Chemistry, Pondicherry University, Puducherry 605 014, India   Email: crrnath.che@pondiuni.edu.in
,
Krishna Mukund
Department of Chemistry, Pondicherry University, Puducherry 605 014, India   Email: crrnath.che@pondiuni.edu.in
,
Chinnasamy Ramaraj Ramanathan*
Department of Chemistry, Pondicherry University, Puducherry 605 014, India   Email: crrnath.che@pondiuni.edu.in
› Author Affiliations
Further Information

Publication History

Received: 30 August 2016

Accepted after revision: 08 October 2016

Publication Date:
24 November 2016 (online)


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.

Supporting Information

 
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