Tuning the Annulation Reactivity of Vinyl Azides and Carbazates: A Divergent Synthesis of Aza-pyrimidinones and Imidazoles

Organic Letters
Jiaan ShaoYongping Yu

Abstract

A divergent cascade annulation has been developed using readily available vinyl azides and carbazates with a wide range of substituents. Vinyl azides were successfully applied as bifunctional partners to prepare aza-pyrimidinones via 6-ring closure with carbazates as well as to construct polyfunctionalized imidazoles via 5-ring closure with N-substituted carbazates. The aza-heterocycles were obtained with high levels of chemoselectivity and excellent yields.

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Citations

Nov 26, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Guili ZhuBo Liu
Sep 29, 2015·Chemical Communications : Chem Comm·Jean-François Vincent-RocanAndré M Beauchemin
Sep 15, 2020·Chemical Society Reviews·Irina P BeletskayaMiguel Yus

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