Literature DB >> 28111956

Isatin N,N'-Cyclic Azomethine Imine 1,3-Dipole and Abnormal [3 + 2]-Cycloaddition with Maleimide in the Presence of 1,4-Diazabicyclo[2.2.2]octane.

Xiao Wang1,2, Peng Yang1,2, Yong Zhang1,2, Chao-Zhe Tang1,2, Fang Tian1, Lin Peng1, Li-Xin Wang1.   

Abstract

A new isatin N,N'-cyclic azomethine imine synthon was devised, and an unexpected abnormal [3 + 2]-cycloaddition with maleimide catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been disclosed. A variety of tricyclic spiropyrrolidine oxindoles bearing a dinitrogen heterocycle and succinimide scaffold were obtained in excellent yields (up to 96%) and diastereoselectivities (up to 97:3) under mild conditions.

Entities:  

Year:  2017        PMID: 28111956     DOI: 10.1021/acs.orglett.6b03815

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  1,3-Dipolar cycloaddition of isatin N,N'-cyclic azomethine imines with α,β-unsaturated aldehydes catalyzed by DBU in water.

Authors:  Zhan-Yong Wang; Ting Yang; Rongxiang Chen; Xueji Ma; Huan Liu; Kai-Kai Wang
Journal:  RSC Adv       Date:  2020-06-25       Impact factor: 4.036

2.  A [3 + 2] cycloaddition/C-arylation of isatin N,N'-cyclic azomethine imine 1,3-dipole with arynes.

Authors:  Qiaomei Jin; Dongjian Zhang; Jian Zhang
Journal:  RSC Adv       Date:  2020-08-19       Impact factor: 4.036

  2 in total

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