A Cu2O/TBAB-promoted approach to synthesize heteroaromatic 2-amines via one-pot cyclization of aryl isothiocyanates with ortho-substituted amines in water

Jinli Zhang; Ling Chen; Yibo Dong; Jinchen Yang; Yangjie Wu

doi:10.1039/D0OB01431A

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A Cu₂O/TBAB-promoted approach to synthesize heteroaromatic 2-amines via one-pot cyclization of aryl isothiocyanates with ortho-substituted amines in water†

Jinli Zhang,

*^ab Ling Chen,^a Yibo Dong,^a Jinchen Yang^b and Yangjie Wu

^ab

Author affiliations

* Corresponding authors

^a Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou, P.R. China
E-mail: jinli@zzu.edu.cn

^b College of Chemistry, Green Catalytic Center, Zhengzhou University, Zhengzhou 450001, P. R. China

Abstract

An efficient approach to synthesize heteroaromatic 2-amines from one-pot desulfurization/dehydrogenative cyclization of aryl isothiocyanates with ortho-substituted amines in water was developed. This approach tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to synthesize heteroaromatic 2-amines in moderate to excellent yields. A plausible mechanism was proposed and the role of TBAB and Cu₂O in the present strategy was suggested with the help of ESI mass spectrometry.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB01431A
Article type: Paper
Submitted: 11 Jul 2020
Accepted: 06 Sep 2020
First published: 08 Sep 2020

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Org. Biomol. Chem., 2020,18, 7425-7430

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A Cu₂O/TBAB-promoted approach to synthesize heteroaromatic 2-amines via one-pot cyclization of aryl isothiocyanates with ortho-substituted amines in water

J. Zhang, L. Chen, Y. Dong, J. Yang and Y. Wu, Org. Biomol. Chem., 2020, 18, 7425 DOI: 10.1039/D0OB01431A

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Organic & Biomolecular Chemistry