GENERAL AND EFFICIENT ONE-POT SYNTHESIS OF <i>N</i>-SUBSTITUTED 7-BROMO-2,3-DIHYDRO-1<i>H</i>-PYRROLO[3,4-<i>b</i>]QUINOLIN-1-ONES

Authors

  • Yang Li Institute of Superfine Chemicals, Bohai University, Jinzhou, 121000
  • Kai Li Institute of Superfine Chemicals, Bohai University, Jinzhou, 121000
  • Wentao Gao Institute of Superfine Chemicals, Bohai University, Jinzhou, 121000

DOI:

https://doi.org/10.1007/3016

Keywords:

amine, isoindolin-l-one, quinoline, intramolecular cyclization, Williamson-type reaction

Abstract

A simple and general synthesis of a series of quinoline-based isoindolin-1-ones, namely N-substituted 7-bromo-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-ones through a one-pot reaction of ethyl 6-bromo-2-(chloromethyl)quinoline-3-carboxylate with various amines in refluxing EtOH–AcOH (v/v, 10:1) solvent system was described. A mechanism involving consecutive Williamson-type reaction of the 2-chloromethyl group with amine followed by intramolecular C–N bond cyclization process is proposed.

How to Cite
Li, Y.; Li, K.; Gao, W. Chem. Heterocycl. Compd. 2016, 52, 200. [Khim. Geterotsikl. Soedin. 2016, 52, 200.]

For this article in the English edition see DOI 10.1007/s10593-016-1856-0

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Published

2016-04-11

Issue

Vol. 52 No. 3 (2016)

Section

Original Papers