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

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...

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Veröffentlicht in:Organic & biomolecular chemistry 2020-09, Vol.18 (37), p.7425-7430
Hauptverfasser: Zhang, Jinli, Chen, Ling, Dong, Yibo, Yang, Jinchen, Wu, Yangjie
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01431a