Transition-Metal-Free [3 + 2] Cycloaddition of Nitroolefins and Diazoacetonitrile: A Facile Access to Multisubstituted Cyanopyrazoles

Zhen Chen; Yue Zhang; Jing Nie; Jun-An Ma

doi:10.1021/acs.orglett.8b00729

Transition-Metal-Free [3 + 2] Cycloaddition of Nitroolefins and Diazoacetonitrile: A Facile Access to Multisubstituted Cyanopyrazoles

Org Lett. 2018 Apr 6;20(7):2120-2124. doi: 10.1021/acs.orglett.8b00729. Epub 2018 Mar 26.

Authors

Zhen Chen¹, Yue Zhang¹, Jing Nie¹, Jun-An Ma¹

Affiliation

¹ Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Center of Chemical Science & Engineering , Tianjin University , Tianjin 300072 , P. R. of China.

PMID: 29578724
DOI: 10.1021/acs.orglett.8b00729

Abstract

A transition-metal-free [3 + 2] cycloaddition reaction between nitroolefins and diazoacetonitrile (N₂CHCN) is described. This protocol exhibits several merits including simple starting materials, mild reaction conditions, broad substrate scope, good yields, and regioselectivities. The one-pot three-component reaction of nitroolefins with diazoacetonitrile (N₂CHCN) and alkyl halides is also developed, thus delivering a series of multisubstituted cyanopyrazoles in good to high yields.

Publication types

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