Issue 35, 2023
From the journal:

Organic & Biomolecular Chemistry

Rearrangement of 2-(benzofuran-2-yl)-3-phenylpyridines via photoinduced 6π-electrocyclization†

Jin Xi,a   Ding Wang, ORCID logo a   Jinxia Hu,a   Huan Shen,a   Tao Wang ORCID logo a  and  Zunting Zhang ORCID logo *a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China
E-mail: zhangzt@snnu.edu.cn

Abstract

By photoinduced 6π-electrocyclization of 2-(benzofuran-2-yl)-3-phenylpyridine derivatives 1, a method for the synthesis of trans-dihydrobenzo[f]quinolines 2, cis-dihydrobenzo[f]quinolines 3 and 8b-methyl-1,8b-dihydrobenzo[f]quinolines 4 was developed. Irradiation of 2-(benzofuran-2-yl)-3-phenylpyridine 1 in acetone–H2O (5 : 1, v/v) with a 313 nm UV lamp under an argon atmosphere at room temperature successfully yielded 2, which was further converted into 3 at elevated temperature (200 °C) in glycerol. However, irradiating 2-(3-methylbenzofuran-2-yl)-3-phenylpyridines 1 in CH2Cl2 with a 254 nm UV lamp gave 4 in good yields. The syntheses of 2, 3 and 4via the 6π-electrocyclization rearrangement of 1 not only offer high atom efficiency but also do not require transition metal catalysts or additives.

Graphical abstract: Rearrangement of 2-(benzofuran-2-yl)-3-phenylpyridines via photoinduced 6π-electrocyclization

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Article information

DOI
https://doi.org/10.1039/D3OB00883E
Article type
Paper
Submitted
02 Jun 2023
Accepted
14 Jul 2023
First published
18 Aug 2023

Org. Biomol. Chem., 2023,21, 7188-7193

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Rearrangement of 2-(benzofuran-2-yl)-3-phenylpyridines via photoinduced 6π-electrocyclization

J. Xi, D. Wang, J. Hu, H. Shen, T. Wang and Z. Zhang, Org. Biomol. Chem., 2023, 21, 7188 DOI: 10.1039/D3OB00883E

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