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Issue 35, 2014
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Scandium-catalyzed tandem selective oxirane ring-opening/Friedel–Crafts alkylation: a facile access to [1,4]oxazino[4,3-a]indoles and 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines

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Abstract

A facile technique involving a novel Lewis-acid-catalyzed tandem selective ring-opening of oxirane and Friedel–Crafts alkylation of 1H-indol-1-yl derived oxiranes was developed. The developed protocol affords functionalized [1,4]oxazino[4,3-a]indoles and 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines in up to 95% yield.

Graphical abstract: Scandium-catalyzed tandem selective oxirane ring-opening/Friedel–Crafts alkylation: a facile access to [1,4]oxazino[4,3-a]indoles and 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines

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Article information


Submitted
22 May 2014
Accepted
04 Jul 2014
First published
08 Jul 2014

Org. Biomol. Chem., 2014,12, 6869-6877
Article type
Paper

Scandium-catalyzed tandem selective oxirane ring-opening/Friedel–Crafts alkylation: a facile access to [1,4]oxazino[4,3-a]indoles and 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines

L. Wei, L. Liu and J. Zhang, Org. Biomol. Chem., 2014, 12, 6869
DOI: 10.1039/C4OB01057D

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