Issue 80, 2017

A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles

Abstract

A regio- and stereoselective thiocyanate addition to ynones is achieved using KSCN in AcOH at 70 °C. The reaction is extendable to ynals, ynesulfones, ynoic acids and ynoates. Adducts from ynones were readily transformed into thiazine-2-thione derivatives under slightly modified reaction conditions. In contrast, thiocyanated adducts from ynamides underwent an in situ decyanative amido cyclization towards isothiazolones. None of these events needed any transition metal or catalyst, attaining a high synthetic value.

Graphical abstract: A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles

Supplementary files

Article information

Article type
Communication
Submitted
03 Aug 2017
Accepted
19 Sep 2017
First published
19 Sep 2017

Chem. Commun., 2017,53, 11060-11063

A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles

V. Dwivedi, M. Rajesh, R. Kumar, R. Kant and M. Sridhar Reddy, Chem. Commun., 2017, 53, 11060 DOI: 10.1039/C7CC06081E

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