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Issue 2, 2017
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Synthesis of 4-substituted 3-(2-hydroxyphenyl)-quinolines through an unexpected iron(iii) chloride promoted reaction of cyclic imine dibenzo[b,f][1,4]oxazepines with alkynes

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Abstract

An unexpected FeCl3-promoted reaction of cyclic imine dibenzo[b,f][1,4]oxazepines with alkynes was studied, leading to a series of 4-substituted 3-(2-hydroxyphenyl)-quinolines. A variety of substituted cyclic imines and terminal alkynes (arylacetylenes, conjugated enynes, and 1,3-diynes) were used for this reaction type resulting in the formation of the corresponding products in yields ranging from 34 to 88%. A reasonable reaction mechanism involving a tandem reaction procedure was proposed on the basis of control experiments. The reaction sequence demonstrated herein represents an efficient, yet practical method for the synthesis of novel 4-substituted 3-(2-hydroxyphenyl)-quinoline derivatives.

Graphical abstract: Synthesis of 4-substituted 3-(2-hydroxyphenyl)-quinolines through an unexpected iron(iii) chloride promoted reaction of cyclic imine dibenzo[b,f][1,4]oxazepines with alkynes

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Supplementary files

Article information


Submitted
15 Sep 2016
Accepted
05 Nov 2016
First published
07 Nov 2016

Org. Chem. Front., 2017,4, 196-203
Article type
Research Article

Synthesis of 4-substituted 3-(2-hydroxyphenyl)-quinolines through an unexpected iron(III) chloride promoted reaction of cyclic imine dibenzo[b,f][1,4]oxazepines with alkynes

C. Zhu, Z. Deng, Y. Zhang and Y. Wang, Org. Chem. Front., 2017, 4, 196 DOI: 10.1039/C6QO00545D

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