Issue 17, 2015

Facile synthesis of benzoindoles and naphthofurans through carbonaceous material-catalyzed cyclization of naphthylamines/naphthols with nitroolefins in water

Abstract

A facile and efficient approach has been established for the synthesis of benzoindole and naphthofuran derivatives via the metal-free cyclization reaction of nitroolefins with naphthylamines/naphthols. Various substituted benzoindoles and naphthofurans are obtained in good to excellent yields. Moreover, the ability to recycle the carbonaceous material makes this method quite cost-effective and environmentally benign compared to traditional acid-catalyzed methods. Theoretical studies indicated that the reaction between naphthylamine and nitroolefin catalyzed by this solid acid was thermodynamically controlled at 60 °C, resulting in the formation of the benzoindoles.

Graphical abstract: Facile synthesis of benzoindoles and naphthofurans through carbonaceous material-catalyzed cyclization of naphthylamines/naphthols with nitroolefins in water

Supplementary files

Article information

Article type
Paper
Submitted
22 Jan 2015
Accepted
19 Mar 2015
First published
19 Mar 2015

Org. Biomol. Chem., 2015,13, 5022-5029

Facile synthesis of benzoindoles and naphthofurans through carbonaceous material-catalyzed cyclization of naphthylamines/naphthols with nitroolefins in water

F. Zhang, C. Li, C. Wang and C. Qi, Org. Biomol. Chem., 2015, 13, 5022 DOI: 10.1039/C5OB00129C

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