[3 + 2]-Annulations of N-alkyl-3-substituted indoles with quinone monoketals catalysed by Brønsted acids

Zhuo Chai; Jia-Nan Chen; Zhen Liu; Xue-Fei Li; Pei-Jun Yang; Ji-Ping Hu; Gaosheng Yang

doi:10.1039/C5OB01876E

[3 + 2]-Annulations of N-alkyl-3-substituted indoles with quinone monoketals catalysed by Brønsted acids

Zhuo Chai,*^a^b Jia-Nan Chen,^a Zhen Liu,^a Xue-Fei Li,^a Pei-Jun Yang,^a Ji-Ping Hu^a and Gaosheng Yang^a

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* Corresponding authors

^a Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, China
E-mail: chaizhuo@mail.ahnu.edu.cn, gshyang@mail.ahnu.edu.cn

^b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China

Abstract

An organocatalytic dearomative [3 + 2]-annulation of N-alkyl-3-alkylindoles with quinone monoketals is developed. The reaction provides a mild and straightforward way to various benzofuro[2,3-b]indolines of potential biological and pharmaceutical interest in moderate to good yields. Moreover, when 3-phenylindole, a problematic substrate in previous relevant studies, was used as the substrate under the otherwise same reaction conditions, a novel 1,2-shift of the phenyl group occurred followed by aromatization to provide 2,3-diaryl indoles useful for cancer therapy studies in moderate yields.

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Publication details

The article was received on 09 Sep 2015, accepted on 26 Nov 2015 and first published on 26 Nov 2015

Article type: Paper

DOI: 10.1039/C5OB01876E

Author version available: Download Author version (PDF)

Citation: Org. Biomol. Chem., 2016,14, 1024-1030

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[3 + 2]-Annulations of N-alkyl-3-substituted indoles with quinone monoketals catalysed by Brønsted acids

Z. Chai, J. Chen, Z. Liu, X. Li, P. Yang, J. Hu and G. Yang, Org. Biomol. Chem., 2016, 14, 1024
DOI: 10.1039/C5OB01876E
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Organic & Biomolecular Chemistry

[3 + 2]-Annulations of N-alkyl-3-substituted indoles with quinone monoketals catalysed by Brønsted acids

Abstract

Supplementary files

Publication details

[3 + 2]-Annulations of N-alkyl-3-substituted indoles with quinone monoketals catalysed by Brønsted acids

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