5 years ago

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

Development and Cycloaddition Reactivity of a New Class of Pyridine-Based Mesoionic 1,3-Dipole
Evan N. Keyzer, Huseyin Erguven, David C. Leitch, Bruce A. Arndtsen
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. Modular approach: A new class of mesoionic 1,3-dipole has been formed by reaction of pyridinyl-acid chlorides and imines. The modularity of this synthesis can be employed to build-up families of dipoles where every substituent can be modified in one step. Reactivity studies show these dipoles undergo facile 1,3-dipolar cycloaddition with alkynes to form indolizines.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201609726

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