Fan Jinming, Zhang Wei, Gao Wangxi, Wang Tao, Duan Wei-Liang, Liang Yong, Zhang Zunting
Key Laboratory of Applied Surface and Colloid Chemistry (Ministry of Education), School of Chemistry and Chemical Engineering , Shaanxi Normal University , Xi'an 710119 , People's Republic of China.
Org Lett. 2019 Nov 15;21(22):9183-9187. doi: 10.1021/acs.orglett.9b03556. Epub 2019 Nov 5.
A strategy for the syntheses of benzofuranoquinolines and its analogues via the irradiation of -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 H evolution was elucidated. Notably, the syntheses of -8b-methyl-8b,13a-dihydrobenzo[]benzofuro[3,2-]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.
描述了一种在氩气气氛下，于室温下用紫外光照射二氯甲烷中的对苯基呋喃基/噻吩基吡啶/嘧啶来合成苯并呋喃喹啉及其类似物的策略。阐明了该反应通过6π-电环化、[1,5]-氢迁移和1,3-烯胺互变异构导致氢气释放的过程的机理。值得注意的是，通过与该反应机理相关的2-(3-甲基苯并呋喃-2-基)-3-苯基吡啶的光诱导重排合成-8b-甲基-8b,13a-二氢苯并[]苯并呋喃[3,2-]喹啉突出了所开发方法的重要性。
