Literature DB >> 28004875

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

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

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.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Year:  2016        PMID: 28004875     DOI: 10.1002/anie.201609726

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

1.  Influence of Endo- and Exocyclic Heteroatoms on Stabilities and 1,3-Dipolar Cycloaddition Reactivities of Mesoionic Azomethine Ylides and Imines.

Authors:  Pier Alexandre Champagne; K N Houk
Journal:  J Org Chem       Date:  2017-10-06       Impact factor: 4.354

2.  Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans.

Authors:  Huseyin Erguven; Cuihan Zhou; Bruce A Arndtsen
Journal:  Chem Sci       Date:  2021-10-27       Impact factor: 9.825

3.  The synthesis of imidazo[1,5-a]quinolines via a decarboxylative cyclization under metal-free conditions.

Authors:  Zicong Yan; Changfeng Wan; Yu Yang; Zhenggen Zha; Zhiyong Wang
Journal:  RSC Adv       Date:  2018-06-25       Impact factor: 3.361

4.  Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes.

Authors:  Sébastien A Roy; José Zgheib; Cuihan Zhou; Bruce A Arndtsen
Journal:  Chem Sci       Date:  2020-12-22       Impact factor: 9.825

  4 in total

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