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Synthesis of Trans ‐4 a ,12 b /3,4‐Dihydrodibenzo[ f , h ]quinolin‐2(1 H )‐Ones and Dibenzo[ f , h ]quinolin‐2(1 H )‐Ones via Irradiation of 6‐Biphenylpyridine‐2(1 H )‐Ones
Author(s) -
Sui Jingzhi,
He Yun,
Wang Tao,
Liang Yong,
Zhang Zunting
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100509
Subject(s) - chemistry , annulation , pyridine , biphenyl , stereochemistry , irradiation , medicinal chemistry , organic chemistry , catalysis , physics , nuclear physics
Abstract The synthesis of trans ‐4 a ,12 b ‐dihydrodibenzo[ f , h ]quinolin‐2(1 H )‐ones ( 2) , dibenzo[ f , h ]quinolin‐2(1 H )‐ones (3) and 3,4‐dihydrodibenzo[ f , h ]quinolin‐2(1 H )‐ones ( 4) via photo‐induced annulation of 6‐([1,1′‐biphenyl]‐2‐yl)pyridine‐2(1 H )‐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 .