Synthesis of Trans‐4a,12b/3,4‐Dihydrodibenzoquinolin‐2(1H)‐Ones and Dibenzoquinolin‐2(1H)‐Ones via Irradiation of 6‐Biphenylpyridine‐2(1H)‐Ones

The synthesis of trans‐4a,12b‐dihydrodibenzo[f,h]quinolin‐2(1H)‐ones (2), dibenzo[f,h]quinolin‐2(1H)‐ones (3) and 3,4‐dihydrodibenzo[f,h]quinolin‐2(1H)‐ones (4) via photo‐induced annulation of 6‐([1,1′‐biphenyl]‐2‐yl)pyridine‐2(1H)‐ones (1) under irradiation of a 313 nm UV light was described. Compo...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-07, Vol.363 (14), p.3554-3559
Main Authors: Sui, Jingzhi, He, Yun, Wang, Tao, Liang, Yong, Zhang, Zunting
Format: Article
Language:English
Subjects:
Chemical reactions
Iodine
Irradiation
Synthesis
Ultraviolet radiation
Online Access:Get full text
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Summary:The synthesis of trans‐4a,12b‐dihydrodibenzo[f,h]quinolin‐2(1H)‐ones (2), dibenzo[f,h]quinolin‐2(1H)‐ones (3) and 3,4‐dihydrodibenzo[f,h]quinolin‐2(1H)‐ones (4) via photo‐induced annulation of 6‐([1,1′‐biphenyl]‐2‐yl)pyridine‐2(1H)‐ones (1) under irradiation of a 313 nm UV light was described. Compounds 2 were obtained in 82–95% yields when the irradiation time was 3 h. Products 3 were obtained by irradiating 1 for 12 h in the presence of iodine. Heating the solutions of 2 in DMF at 130 °C for 24 h gave compounds 4 via a double 1,3‐H shift. The demonstrated protocols showed the diversity of photo‐induced cyclization of compounds 1.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100509