Copper-catalyzed [2+3]-annulation of N–H imines with vinyl azides: access to polyaryl 2H-imidazoles
- 7 April 2020
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 56 (42), 5621-5624
- https://doi.org/10.1039/c9cc10042c
Abstract
A practical method for the synthesis of 2H-imidazoles via a [2+3] annulation of N–H imines with vinyl azides using a copper catalyst is developed. In this conversion, environmentally friendly oxygen is used as the sole oxidant and N2 and H2O are the only by-products. The catalytic transformation, operating under mild conditions, is operationally simple and is considered as a readily available catalytic system having good substrate and functional compatibility with high atom-efficiency without the need for additional ligands or additives.Keywords
Funding Information
- Department of Education of Guangdong Province (2018KZDXM070, 2017KZDXM085, 2019KZDXM052)
- Wuyi University (2019td06)
- National College Students Innovation and Entrepreneurship Training Program (201911349030, S201911349104)
This publication has 49 references indexed in Scilit:
- Design and synthesis of new ruthenium polypyridyl complexes with potent antitumor activity in vitroSpectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019
- Palladium‐Catalyzed Primary Amine‐Directed Decarboxylative Annulation of α‐Oxocarboxylic Acids: Access to Indolo[1,2‐a]quinazolinesAdvanced Synthesis & Catalysis, 2019
- Recent Advances in Pd‐Catalyzed Cross‐Coupling Reaction in Ionic LiquidsEuropean Journal of Organic Chemistry, 2018
- Copper‐Mediated Late‐Stage Functionalization of Heterocycle‐Containing MoleculesAngewandte Chemie, 2017
- O-Acyl oximes: versatile building blocks for N-heterocycle formation in recent transition metal catalysisOrganic & Biomolecular Chemistry, 2015
- A review on anticancer potential of bioactive heterocycle quinolineEuropean Journal of Medicinal Chemistry, 2015
- Complex N-Heterocycle Synthesis via Iron-Catalyzed, Direct C–H Bond AminationScience, 2013
- Tandem reactions initiated by copper-catalyzed cross-coupling: A new strategy towards heterocycle synthesisOrganic & Biomolecular Chemistry, 2011
- Heterocycle synthesis by copper facilitated addition of heteroatoms to alkenes, alkynes and arenesChemical Society Reviews, 2007
- Potent, Orally Active Heterocycle-Based Combretastatin A-4 Analogues: Synthesis, Structure−Activity Relationship, Pharmacokinetics, and In Vivo Antitumor Activity EvaluationJournal of Medicinal Chemistry, 2002