Visible-light-mediated reaction: synthesis of quinazolinones from 1,2-dihydroquinazoline 3-oxides

1-Methyl-2-phenylquinazolin-4(1 H )-ones were synthesized in good yield by exposing 1,4-dimethyl-2-phenyl-1,2-dihydroquinazoline 3-oxides or 1-methyl-2-phenyl-1,2-dihydroquinazoline 3-oxides to visible light in acetonitrile in the absence of any external photosensitizers. The key intermediate for th...

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Bibliographic Details
Published in:RSC advances 2016-01, Vol.6 (7), p.65988-65994
Main Authors: Wu, Chun-Ku, Yang, Ding-Yah
Format: Article
Language:English
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Summary:1-Methyl-2-phenylquinazolin-4(1 H )-ones were synthesized in good yield by exposing 1,4-dimethyl-2-phenyl-1,2-dihydroquinazoline 3-oxides or 1-methyl-2-phenyl-1,2-dihydroquinazoline 3-oxides to visible light in acetonitrile in the absence of any external photosensitizers. The key intermediate for this photochemical reaction was isolated and identified as 1-methyl-2-phenyl-1,4-dihydroquinazolin-4-ol. The mechanism of this photosensitizer-free, visible-light-mediated reaction was proposed. The first example of methane evolution involving cleavage of a C(sp 3 )-CH 3 bond of quinazoline 3-oxide via visible light irradiation is reported.
ISSN:2046-2069
2046-2069
DOI:10.1039/c6ra13972h