Issue 4, 2021

Synthesis of substituted anilines via a gold-catalyzed three-component reaction

Abstract

A three-component reaction for the synthesis of substituted anilines by a gold(I)-catalyzed domino reaction was developed. Cationic gold catalysts selectively and sequentially activated two different alkynes, which were involved in pyrrole synthesis and subsequent Diels–Alder reaction. The sequential formal (3 + 2) annulation/Diels–Alder reaction of three components provided a variety of substituted anilines in a modular fashion. Moreover, utility of the aniline products was demonstrated by derivatization to substituted benzoxazines, which are pharmaceutically important heterocycles.

Graphical abstract: Synthesis of substituted anilines via a gold-catalyzed three-component reaction

Supplementary files

Article information

Article type
Communication
Submitted
02 oct. 2020
Accepted
31 oct. 2020
First published
02 nov. 2020

Org. Biomol. Chem., 2021,19, 765-769

Synthesis of substituted anilines via a gold-catalyzed three-component reaction

H. Ueda, R. Yamamoto, M. Yamaguchi and H. Tokuyama, Org. Biomol. Chem., 2021, 19, 765 DOI: 10.1039/D0OB02018D

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