Assembly of iodinated indolo[1,2-c]quinazoline amines via I2/CHP-promoted cascade annulation of isocyanides and diarylalkynes

Min Zhang; Meng Li; Huanfeng Jiang; Biao Nie; Wanqing Wu

doi:10.1039/D3QO00799E

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Assembly of iodinated indolo[1,2-c]quinazoline amines via I₂/CHP-promoted cascade annulation of isocyanides and diarylalkynes†

Min Zhang,^a Meng Li,^a Huanfeng Jiang,

^a Biao Nie*^b and Wanqing Wu

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China
E-mail: cewuwq@scut.edu.cn
Fax: (+86) 20-87112906

^b State Key Laboratory of Anti-Infective Drug Development, Sunshine Lake Pharma Company, Ltd, Dongguan 523871, China
E-mail: niebiao@hec.cn

Abstract

Herein, a straightforward and efficient approach to iodinated indolo[1,2-c]quinazoline amines via I₂/cumene hydroperoxide (CHP)-promoted cascade annulation of diarylalkynes and isocyanides has been described. This method features excellent regio- and chemoselectivities, good functional group compatibility, and mild reaction conditions. Mechanistic studies suggest that CHP is essential to the catalytic cycle of the reaction. The newly formed indolo[1,2-c]quinazoline scaffolds can be further modified, showing potential applications in medicinal chemistry and materials science.

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Article information

DOI: https://doi.org/10.1039/D3QO00799E
Article type: Research Article
Submitted: 29 May 2023
Accepted: 11 Jul 2023
First published: 20 Jul 2023

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Org. Chem. Front., 2023,10, 4305-4310

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Assembly of iodinated indolo[1,2-c]quinazoline amines via I₂/CHP-promoted cascade annulation of isocyanides and diarylalkynes

M. Zhang, M. Li, H. Jiang, B. Nie and W. Wu, Org. Chem. Front., 2023, 10, 4305 DOI: 10.1039/D3QO00799E

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