Issue 24, 2022

Catalyst- and additive-free [3 + 3] cyclization–aromatization of β,γ-dioxobutanoate with amines for synthesis of p-aminophenols

Abstract

Cyclization–aromatization of enamines is a powerful method for the establishment of aza-aromatic cycles. We report herein the development of a simple and practical [3 + 3] aldol cyclization–aromatization of β,γ-dioxobutanoate with amines for the synthesis of p-aminophenols. Reactions with primary, secondary, benzyl and aryl amines all proceeded smoothly under mild reaction conditions, without catalysts and additives. Sensitive functionalities and heterocycles such as alcohol, ether, halogen, carboxylic acid, alkyne, pyridine, imidazole and free (N–H) indole, which could interfere with metal-, or acid-mediated processes, were well tolerated. The high degree of compatibility and practicability of this method is demonstrated by the late-stage cyclization–aromatization of structurally complex drug molecules.

Graphical abstract: Catalyst- and additive-free [3 + 3] cyclization–aromatization of β,γ-dioxobutanoate with amines for synthesis of p-aminophenols

Supplementary files

Article information

Article type
Paper
Submitted
21 Oct 2022
Accepted
23 Nov 2022
First published
24 Nov 2022

Green Chem., 2022,24, 9690-9696

Catalyst- and additive-free [3 + 3] cyclization–aromatization of β,γ-dioxobutanoate with amines for synthesis of p-aminophenols

H. Qian, C. Wang, Z. Shen, M. Sun, H. Zhang, S. Fan, J. Feng, S. Liu and Z. Zhang, Green Chem., 2022, 24, 9690 DOI: 10.1039/D2GC03936B

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