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

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,...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 24; no. 24; pp. 969 - 9696
Main Authors Qian, Hang, Wang, Cui-Cui, Shen, Zi-Chen, Sun, Ming-Xue, Zhang, Hong-Chao, Fan, Shiming, Feng, Juan, Liu, Shouxin, Zhang, Zhi-Wei
Format Journal Article
Published 12.12.2022
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Summary: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. A [3 + 3] cyclization-aromatization of β,γ-dioxobutanoate with amines for synthesis of p -aminophenols under catalyst- and additive-free conditions was developed. The reaction displays high efficiency in the late-stage modification of drug molecules.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
2209775
https://doi.org/10.1039/d2gc03936b
ISSN:1463-9262
1463-9270
DOI:10.1039/d2gc03936b