Issue 18, 2020
From the journal:

Organic Chemistry Frontiers

Synthesis of 2,3-disubstituted indoles via a tandem reaction†

Shiqiang Ma,a   Dan Long,a   Peiqi Chen,a   Hongliang Shi,a   Huilin Li,a   Ran Fang, ORCID logo a   Xiaolei Wang,a   Xingang Xie ORCID logo a  and  Xuegong She ORCID logo *a  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China
E-mail: shexg@lzu.edu.cn

Abstract

A strategy for the synthesis of 2,3-disubstituted indoles from 2-allyl-2-(2-nitrophenyl)cyclohexane-1,3-dione has been developed. A wide array of 2,3-disubstituted indoles were accessed in modest to good yields via a tandem reduction/condensation/fragmentation/cyclization sequence. The utility of this strategy was exemplified in the formal syntheses of leucomidine A and goniomitine. The mechanism was confirmed by experiments and density functional theory (DFT) calculations. Differential fragmentation made the reaction more complicated.

Graphical abstract: Synthesis of 2,3-disubstituted indoles via a tandem reaction

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Article information

DOI
https://doi.org/10.1039/D0QO00765J
Article type
Research Article
Submitted
29 Jun 2020
Accepted
08 Aug 2020
First published
11 Aug 2020

Org. Chem. Front., 2020,7, 2689-2695

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Synthesis of 2,3-disubstituted indoles via a tandem reaction

S. Ma, D. Long, P. Chen, H. Shi, H. Li, R. Fang, X. Wang, X. Xie and X. She, Org. Chem. Front., 2020, 7, 2689 DOI: 10.1039/D0QO00765J

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