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Issue 37, 2019
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Intramolecular azavinyl carbene-triggered rearrangement of furans

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Abstract

An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads to valuable 2-formyl- and 2-acetylpyridine building blocks, which could be obtained in one-pot starting from easily accessible (furan-2-ylmethyl)propargyl amines. An original method for the synthesis of highly functionalized indolizines from the obtained pyridines has been proposed.

Graphical abstract: Intramolecular azavinyl carbene-triggered rearrangement of furans

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Supplementary files

Article information


Submitted
11 May 2019
Accepted
16 Jul 2019
First published
26 Jul 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 8583-8588
Article type
Edge Article

Intramolecular azavinyl carbene-triggered rearrangement of furans

A. S. Makarov, M. G. Uchuskin and A. S. K. Hashmi, Chem. Sci., 2019, 10, 8583
DOI: 10.1039/C9SC02299F

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