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Issue 97, 2017
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Catalytic substitution/cyclization sequences of O-substituted Isocyanates: synthesis of 1-alkoxybenzimidazolones and 1-alkoxy-3,4-dihydroquinazolin-2(1H)-ones

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Abstract

O-Substituted isocyanates (O-isocyanates) have rarely been used in organic synthesis, given their tendency to undergo side reactions (e.g., trimerization). Herein, we show that masked (blocked) O-isocyanate precursors allow one-pot or cascade reaction sequences featuring base-catalyzed substitution with 2-iodoanilines and 2-iodobenzylamines followed by copper-catalyzed cyclization, to form benzimidazolones and 3,4-dihydroquinazolin-2(1H)-ones. This work shows that O-isocyanates can serve as efficient building blocks for the synthesis of hydroxylamine-containing heterocycles.

Graphical abstract: Catalytic substitution/cyclization sequences of O-substituted Isocyanates: synthesis of 1-alkoxybenzimidazolones and 1-alkoxy-3,4-dihydroquinazolin-2(1H)-ones

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Article information


Submitted
13 Oct 2017
Accepted
14 Nov 2017
First published
22 Nov 2017

Chem. Commun., 2017,53, 13055-13058
Article type
Communication

Catalytic substitution/cyclization sequences of O-substituted Isocyanates: synthesis of 1-alkoxybenzimidazolones and 1-alkoxy-3,4-dihydroquinazolin-2(1H)-ones

Q. Wang, J. An, H. Alper, W. Xiao and A. M. Beauchemin, Chem. Commun., 2017, 53, 13055
DOI: 10.1039/C7CC07926E

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