Azepine synthesis from alkyl azide and propargylic ester via gold catalysis

The Journal of Organic Chemistry
Heng LiuWen-Xiang Hu

Abstract

An efficient new method was developed to synthesize multisubstituted 4,5-dihydro-1H-azepine derivatives through the gold-catalyzed reaction of two molecules of propargylic esters with one molecule of alkyl azide. It was proposed that vinyl gold carbenoid, in situ generated from propargylic ester through gold-catalyzed 1,2-rearrangement, was trapped by alkyl azide to give vinyl imine intermediate. These, in turn, could undergo a formal [4 + 3] cycloaddition with another molecule of vinyl gold carbenoid to afford the desired azepine product.

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Citations

Sep 9, 2015·The Journal of Organic Chemistry·Mitsuhiro YoshimatsuOsamu Muraoka
Dec 19, 2016·Chemical Communications : Chem Comm·Geoffroy Hervé LoncaFabien Gagosz
May 24, 2018·Chemical Communications : Chem Comm·Augustin PeneauLaurent Chabaud
Oct 23, 2018·Organic & Biomolecular Chemistry·Manickam BakthadossDuddu S Sharada
Jun 10, 2015·Molecular Diversity·Simpal KumariAakanksha Mishra
Jul 27, 2020·Chemistry : a European Journal·Barry M TrostJohnathan E Schultz
Jul 3, 2013·The Journal of Organic Chemistry·Naseem Iqbal, Anne Fiksdahl

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