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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.

ABSTRACT: 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.

SUBMITTER: Zheng J

PROVIDER: S-EPMC8239259 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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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.

Zheng Jie J Meng Shuyu S Wang Quanrui Q

Beilstein journal of organic chemistry 20210622

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. ...[more]

PMID: 34239615

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