Efficient Pd-catalyzed domino synthesis of 1-phenyl-1H-indol-2-amine and 5-amino-indolo[1,2-a]quinazoline derivatives

Min Jiang; Haoyue Xiang; Fangxia Zhu; Xing Xu; Lianfu Deng; Chunhao Yang

doi:10.1039/C5OB01642H

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Efficient Pd-catalyzed domino synthesis of 1-phenyl-1H-indol-2-amine and 5-amino-indolo[1,2-a]quinazoline derivatives†

Min Jiang,^a Haoyue Xiang,^b Fangxia Zhu,^a Xing Xu,^a Lianfu Deng*^a and Chunhao Yang*^b

Author affiliations

* Corresponding authors

^a Shanghai Key Laboratory for Bone and Joint Diseases, Shanghai Institute of Traumatology and Orthopaedics, Shanghai Ruijin Hospital, Shanghai Jiaotong University School of Medicine, Shanghai, P. R. China
E-mail: lf_deng@126.com

^b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, P. R. China
E-mail: chyang@simm.ac.cn
Fax: +86-21-50806770
Tel: +86-21-50806770

Abstract

An efficient and practical one-pot domino synthesis of 1-phenyl-1H-indol-2-amine and 5-amino-indolo[1,2-a]quinazoline derivatives from readily available 2-(2-bromophenyl)acetonitriles was developed. The overall protocol involves a Buchwald–Hartwig type coupling and a base-promoted intramolecular nucleophilic reaction. The reaction scope, advantages and limitations are discussed.

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Article information

DOI: https://doi.org/10.1039/C5OB01642H
Article type: Communication
Submitted: 06 Aug 2015
Accepted: 07 Sep 2015
First published: 07 Sep 2015

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Org. Biomol. Chem., 2015,13, 10122-10126

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Efficient Pd-catalyzed domino synthesis of 1-phenyl-1H-indol-2-amine and 5-amino-indolo[1,2-a]quinazoline derivatives

M. Jiang, H. Xiang, F. Zhu, X. Xu, L. Deng and C. Yang, Org. Biomol. Chem., 2015, 13, 10122 DOI: 10.1039/C5OB01642H

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Organic & Biomolecular Chemistry

Efficient Pd-catalyzed domino synthesis of 1-phenyl-1H-indol-2-amine and 5-amino-indolo[1,2-a]quinazoline derivatives†

Abstract

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Efficient Pd-catalyzed domino synthesis of 1-phenyl-1H-indol-2-amine and 5-amino-indolo[1,2-a]quinazoline derivatives

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