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Short Paper | Regular issue | Vol 91, No. 11, 2015, pp.2180-2189
Published online, 9th October, 2015
DOI: 10.3987/COM-15-13314
A General Synthesis of Novel Quinoline-Based Isoindolin-1-one Derivatives

Hong Zhang and Yang Li*

*Institute of Superfine Chemicals, Bohai University, 19 Keji Road, Jinzhou 121000, China

Abstract

A simple and general one-pot protocol for the synthesis of a series quinoline-based isoindolin-l-ones, namely 7-chloro-2-substituted-2,3-dihydro- 1H-pyrrolo[3,4-b]quinolin-1-ones (5a-p) is described, involving a cascade Williamson-type condensation reaction of ethyl 6-chloro-2-(chloromethyl)- quinoline-3-carboxylate (3) with aromatic amines (4a-i), aliphatic amines (4j-m) and aliphatic diamines (4n-p) and subsequent intramolecular C-N bond cyclization of the resulting intermediates in refluxing EtOH–AcOH (v/v, 10:1) solvent system in a single synthetic operation.