Development and Cycloaddition Reactivity of a New Class of Pyridine-Based Mesoionic 1,3-Dipole

Huseyin Erguven; David C Leitch; Evan N Keyzer; Bruce A Arndtsen

doi:10.1002/anie.201609726

Development and Cycloaddition Reactivity of a New Class of Pyridine-Based Mesoionic 1,3-Dipole

Angew Chem Int Ed Engl. 2017 May 22;56(22):6078-6082. doi: 10.1002/anie.201609726. Epub 2016 Dec 22.

Authors

Huseyin Erguven¹, David C Leitch¹, Evan N Keyzer¹, Bruce A Arndtsen¹

Affiliation

¹ Department of Chemistry, McGill University, 801 Sherbrooke St. W, Montreal, Quebec, H3A 0B8, Canada.

PMID: 28004875
DOI: 10.1002/anie.201609726

Abstract

We describe here the development and structural characterization of a new type of mesoionic 1,3-dipole, which can be generated in the one-step reaction of imines with pyridine- or quinoline-based acid chlorides. Coupling the formation of these dipoles with alkyne cycloaddition can open a general and modular route to synthesize indolizines from combinations of available and diversifiable building blocks.

Keywords: 1,3 dipolar cycloaddition; heterocycles; indolizines; mesoionic dipoles; multicomponent reactions.

Publication types

Research Support, Non-U.S. Gov't