Development and Cycloaddition Reactivity of a New Class of Pyridine‐Based Mesoionic 1, 3‐Dipole. Issue 22 (22nd December 2016)

• Record Type: Journal Article
• Authors: Erguven, Huseyin; Leitch, David C.; Keyzer, Evan N.; Arndtsen, Bruce A.
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 22(2017)
• Page Start: 6078
• Page End: 6082
• Publication Date: 2016-12-22
• Subjects: 1, 3 dipolar cycloaddition -- heterocycles -- indolizines -- mesoionic dipoles -- multicomponent reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201609726
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : 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.