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

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

Org Biomol Chem. 2015 Oct 28;13(40):10122-6. doi: 10.1039/c5ob01642h. Epub 2015 Sep 17.

Authors

Min Jiang¹, Haoyue Xiang, Fangxia Zhu, Xing Xu, Lianfu Deng, Chunhao Yang

Affiliation

¹ Shanghai Key Laboratory for Bone and Joint Diseases, Shanghai Institute of Traumatology and Orthopaedics, Shanghai Ruijin Hospital, Shanghai Jiaotong University School of Medicine, Shanghai, 200025, P. R. China. [email protected].

PMID: 26377704
DOI: 10.1039/c5ob01642h

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Organometallic Compounds / chemistry*
Palladium / chemistry*
Quinazolines / chemical synthesis*
Quinazolines / chemistry

Substances

1-phenyl-1H-indol-2-amine
5-amino-indolo(1,2-a)quinazoline
Indoles
Organometallic Compounds
Quinazolines
Palladium