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Issue 91, 2015
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Diversity-oriented heterocyclic synthesis using divergent reactivity of N-substituted iso(thio)cyanates

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Abstract

Carbon-substituted isocyanates and isothiocyanates are common building blocks in organic synthesis. In contrast, synthetic uses of N-substituted isocyanates and isothiocyanates are severely underdeveloped: few have been reported and their reactivity had not been compared. Herein, we compare the reactivity of blocked (masked) N-isocyanate and N-isothiocyanate precursors in cascade reactions. Divergent reactivity is observed with secondary propargylic and allylic systems, leading to new syntheses of imidazolones, thiazolidines, and a tool to form complex azomethine imines.

Graphical abstract: Diversity-oriented heterocyclic synthesis using divergent reactivity of N-substituted iso(thio)cyanates

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Supplementary files

Article information


Submitted
27 Aug 2015
Accepted
18 Sep 2015
First published
21 Sep 2015

Chem. Commun., 2015,51, 16405-16408
Article type
Communication
Author version available

Diversity-oriented heterocyclic synthesis using divergent reactivity of N-substituted iso(thio)cyanates

J. Vincent-Rocan, J. S. Derasp and A. M. Beauchemin, Chem. Commun., 2015, 51, 16405
DOI: 10.1039/C5CC07212C

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