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

Autor:	Selvaraj Mangalaraj, Kamsali Murali Mohan Achari, Krishna Mukund, Chinnasamy Ramaraj Ramanathan, Jayaraman Selvakumar
Rok vydání:	2016
Předmět:	010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Regioselectivity 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Succinimides chemistry.chemical_compound Succinimide Electrophile Steric factor Triflic acid
Zdroj:	Synthesis. 49:1053-1064
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0036-1588639
Popis:	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.
Databáze:	OpenAIRE
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