Combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement to construct homoallyl sulfur-containing pyrazolones

The first sequentially combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement reaction of α-alkylidene pyrazolinones and propargyl sulfonium salts has been reported to construct homoallyl sulfur-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2019-10, Vol.9 (6), p.34912-34925
Main Authors: Shen, Shou-Jie, Du, Xiao-Li, Xu, Xiao-Li, Wu, Yue-Hua, Zhao, Ming-gang, Liang, Jin-Yan
Format: Article
Language:English
Subjects:
Alkylidene
Chemical reactions
Chemistry
Crystallography
NMR
Nuclear magnetic resonance
Pyrazolones
Reagents
Regioselectivity
Substrates
Sulfonium salts
Sulfur
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:The first sequentially combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement reaction of α-alkylidene pyrazolinones and propargyl sulfonium salts has been reported to construct homoallyl sulfur-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones function as N-nucleophilic agents distinguished from the reported C-addition reactions. Propargyl sulfonium salts were first involved in the [2,3]-sigmatropic rearrangement protocol differentiated from the well-established annulation reactions. The excellent regioselectivity, the broad scope of substrates, gram-scale synthesis and convenient transformation embody the synthetic superiority of this cascade process. The combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement of α-alkylidene pyrazolinones and propargyl sulfonium salts has been reported to construct homoallyl sulfur-containing pyrazolones with moderate to excellent yields.
ISSN:2046-2069
2046-2069
DOI:10.1039/c9ra07610g