Regio- and Stereoselective Switchable Synthesis of (E)- and (Z)-N-Carbonylvinylated Pyrazoles

Author:

Zhang Xue1,Zhang Zheyu1,Yu Haifeng1ORCID,Che Guangbo1

Affiliation:

1. College of Chemistry, Baicheng Normal University, Baicheng 137000, China

Abstract

Regio- and stereoselective switchable synthesis of (E)- and (Z)-N-carbonylvinylated pyrazoles is first developed by using the Michael addition reaction of pyrazoles and conjugated carbonyl alkynes. Ag2CO3 plays a key role in the switchable synthesis of (E)- and (Z)-N-carbonylvinylated pyrazoles. Ag2CO3-free reactions lead to thermodynamically stable (E)-N-carbonylvinylated pyrazoles in excellent yields whereas reactions with Ag2CO3 give (Z)-N-carbonylvinylated pyrazoles in good yields. It is noteworthy that (E)- or (Z)-N1-carbonylvinylated pyrazoles are obtained with high regioselectivity when asymmetrically substituted pyrazoles react with conjugated carbonyl alkynes. The method can also extend to the gram scale. A plausible mechanism is proposed on the basis of the detailed studies, wherein Ag+ acts as coordination guidance.

Funder

Natural Science Foundation of Jilin Province, China

the Foundation of Science and Technology Research Projects of Jilin Provincial Department of Education

the Project of Human Resources and Social Security Department of Jilin Province, China

the Science and Technology Innovation Center Project of Jilin Province, China

the Program for Innovative Research Team of Baicheng Normal University

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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