A strategy
for the syntheses of benzofuranoquinolines and its analogues
via the irradiation of o-phenylfuranyl/thienylpyridines/pyrimidines
in DCM with UV light at rt under an argon atmosphere is described.
The mechanism of this reaction through the process of 6π-electrocyclization,
[1,5]-hydrogen shift, and 1,3-eneamine tautomerism leading to H2 evolution was elucidated. Notably, the syntheses of cis-8b-methyl-8b,13a-dihydrobenzo[f]benzofuro[3,2-h]quinolone via the photoinduced rearrangement of 2-(3-methylbenzofuran-2-yl)-3-phenylpyridine
relevant to the mechanism of this reaction highlights the importance
of the developed methodology.
A concise and environmental friendly protocol has been developed for the synthesis of cis-dihydrochromenones and trans-dihydrochromenones in EtOH at room temperature. Irradiation of 4-phenyl-3-arylcoumarins with a 313 nm UV light...
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