通过光诱导的α-苯基呋喃基吡啶的无受体脱氢环化反应合成苯并呋喃并喹啉及其类似物。
Syntheses of Benzofuranoquinolines and Analogues via Photoinduced Acceptorless Dehydrogenative Annulation of -Phenylfuranylpyridines.
作者信息
Fan Jinming, Zhang Wei, Gao Wangxi, Wang Tao, Duan Wei-Liang, Liang Yong, Zhang Zunting
机构信息
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.
出版信息
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。
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