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Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2021-06-22 , DOI: 10.3762/bjoc.17.104
Jie Zheng 1 , Shuyu Meng 1 , Quanrui Wang 1
Affiliation  

The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF3·Et2O results in an intramolecular Prins reaction affording intermediary benzyl carbenium ions, which are then trapped by a variety of electron-rich aromatics via Friedel–Crafts alkylation. This cascade Prins/Friedel–Crafts cyclization protocol paves an expedient path to medicinally useful 4-aryltetralin-2-ol and 5-aryltetrahydro-5H-benzo[7]annulen-7-ol derivatives.

中文翻译:

用于合成 4-aryltetralin-2-ols 和 5-aryltetrahydro-5H-benzo[7] annulen-7-ols 的级联分子内 Prins/Friedel-Crafts 环化

用 BF 3 ·Et 2 O处理 2-(2-乙烯基苯基) 乙醛或 3-(2-乙烯基苯基) 丙醛导致分子内 Prins 反应,提供中间的苄基碳正离子,然后被各种富电子捕获芳烃通过 Friedel-Crafts 烷基化。这种级联 Prins/Friedel-Crafts 环化方案为获得具有药用价值的 4-aryltetralin-2-ol 和 5-aryltetrahydro-5 H - benzo[7]annulen-7-ol 衍生物铺平了道路。
更新日期:2021-06-22
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