Synthesis of 1,3,5-trisubstituted pyrazoles via 1,3-dipolar cycloaddition of nitrile imines with ninhydrin-derived Morita–Baylis–Hillman carbonates

An effective synthetic method for 1,3,5-trisubstituted pyrazoles via 1,3-dipolar cycloaddition reaction has been developed. This reaction could smoothly proceed between ninhydrin-derived Morita–Baylis–Hillman carbonates and nitrilimines to provide a wide scope of differently substituted pyrazoles in...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-08, Vol.20 (34), p.6923-6930
Main Authors: Wang, Kai-Kai, Li, Yan-Li, Jing, Jun, Chen, Rongxiang, Zhao, Na-Na, Li, Zhi-Hui, Wang, Ming-Yue, Ji, Shuo-Ke
Format: Article
Language:English
Subjects:
Carbonates
Cycloaddition
Imines
Ninhydrin
Pyrazoles
Reaction mechanisms
Regioselectivity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An effective synthetic method for 1,3,5-trisubstituted pyrazoles via 1,3-dipolar cycloaddition reaction has been developed. This reaction could smoothly proceed between ninhydrin-derived Morita–Baylis–Hillman carbonates and nitrilimines to provide a wide scope of differently substituted pyrazoles in high yields (up to 95%). In addition, the reaction mechanism was also proposed to explain its regioselectivity.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01253g