DABCO-Catalyzed Mono-/Diallylation of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates-Reference-Cited by-全球学者库

DABCO-Catalyzed Mono-/Diallylation of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates

Published:2023-03-28 Issue:7 Volume:28 Page:3002
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Wang Qiumi¹,Li Sicheng²,Yang Guosheng¹,Zou Xinyu¹,Yin Xi¹,Feng Juhua¹,Chen Huabao³^ORCID,Yang Chunping³^ORCID,Zhang Li¹,Lu Cuifen⁴,Yue Guizhou¹^ORCID

Affiliation:

1. College of Science, Sichuan Agricultural University, Ya’an 625014, China

2. The Yingjing County Emergency Management Agency, Ya’an 625200, China

3. College of Agronomy, Sichuan Agricultural University, Chengdu 611130, China

4. Hubei Collaborative Innovation Center for Advanced Organochemical Materials, Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062, China

Abstract

Allylation of N-unsubstituted isatin N,N′-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1–10 mol% DABCO in DCM at room temperature, rapidly gave N-allylated and N, β-diallylated isatin N,N′-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts.

Funder

Sichuan Science and Technology Program

the National Key R&D Program of China

the Program Sichuan Veterinary Medicine and Drug Innovation Group of China Agricultural Research System

Publisher

MDPI AG

Subject

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

Link

https://www.mdpi.com/1420-3049/28/7/3002/pdf

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