Issue 39, 2019
From the journal:

Organic & Biomolecular Chemistry

Preparation of spiro[imidazolidine-4,3′-indolin]-2′-imines via copper(i)-catalyzed formal [2 + 2 + 1] cycloaddition of 3-diazoindolin-2-imines and triazines†

Yuxuan Zhou,a   Fanghui Ma,a   Ping Lu ORCID logo *a  and  Yanguang Wang ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
E-mail: pinglu@zju.edu.cn, orgwyg@zju.edu.cn

Abstract

We report a facile and efficient synthesis of spiro[imidazolidine-4,3′-indolin]-2′-imines via a copper(I)-catalyzed cascade reaction of 3-diazoindolin-2-imines with 1,3,5-triazines. The reaction proceeds under very mild conditions and tolerates a variety of functional groups. The cascade process involves the formation of a copper–carbene intermediate and a formal [2 + 2 + 1] cycloaddition.

Graphical abstract: Preparation of spiro[imidazolidine-4,3′-indolin]-2′-imines via copper(i)-catalyzed formal [2 + 2 + 1] cycloaddition of 3-diazoindolin-2-imines and triazines

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Article information

DOI
https://doi.org/10.1039/C9OB01767D
Article type
Paper
Submitted
12 Aug 2019
Accepted
21 Sep 2019
First published
23 Sep 2019

Org. Biomol. Chem., 2019,17, 8849-8852

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Preparation of spiro[imidazolidine-4,3′-indolin]-2′-imines via copper(I)-catalyzed formal [2 + 2 + 1] cycloaddition of 3-diazoindolin-2-imines and triazines

Y. Zhou, F. Ma, P. Lu and Y. Wang, Org. Biomol. Chem., 2019, 17, 8849 DOI: 10.1039/C9OB01767D

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