Ru(II)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for building ring-fused quinazolines and 1,3-benzodiazepines

Yurong Yang; Kaixin Zhang; Jian Yang; Guoxun Zhu; Weijie Chen; Chao Zhang; Zhi Zhou; Wei Yi

doi:10.1039/D0CC04041J

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Ru(ii)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for building ring-fused quinazolines and 1,3-benzodiazepines†

Yurong Yang,‡^a Kaixin Zhang,‡^a Jian Yang,‡^a Guoxun Zhu,^a Weijie Chen,^a Chao Zhang,*^a Zhi Zhou

*^a and Wei Yi

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, Guangdong 511436, P. R. China
E-mail: chao-zh@163.com, zhouzhi@gzhmu.edu.cn, yiwei@gzhmu.edu.cn

Abstract

The Ru(II)-catalyzed tunable [5+1]/[5+2] annulation of N-benzo[d]imidazole indolines with propargyl carbonates has been realized for the divergent synthesis of ring-fused quinazolines and 1,3-benzodiazepines bearing various functional groups. These transformations represent an efficient and practical strategy in constructing complex heterocycles via diversified C–H functionalization. A distinctive acidity-controlled reaction manner has been clarified to account for the chemoselectivity.

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DOI: https://doi.org/10.1039/D0CC04041J
Article type: Communication
Submitted: 10 Jun 2020
Accepted: 07 Aug 2020
First published: 10 Aug 2020

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Chem. Commun., 2020,56, 11315-11318

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Ru(II)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for building ring-fused quinazolines and 1,3-benzodiazepines

Y. Yang, K. Zhang, J. Yang, G. Zhu, W. Chen, C. Zhang, Z. Zhou and W. Yi, Chem. Commun., 2020, 56, 11315 DOI: 10.1039/D0CC04041J

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Chemical Communications

Ru(ii)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for building ring-fused quinazolines and 1,3-benzodiazepines†

Abstract

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Ru(II)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for building ring-fused quinazolines and 1,3-benzodiazepines

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