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1 article(s) from Zheng, Jie

Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols

Jie Zheng,
Shuyu Meng and
Quanrui Wang

Beilstein J. Org. Chem. 2021, 17, 1481–1489, doi:10.3762/bjoc.17.104

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Figure 1: Parent structure of 2,4-disubstituted tetralins (1) and selected medicinally useful derivatives 2–4....

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Scheme 1: Reported strategies for the synthesis of tetralin-2-ol ring systems.

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Scheme 2: Designed cascade reactions to 4-substituted tetralin-2-ols.

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Scheme 3: The documented synthesis of 2-(2-vinylphenyl)acetaldehyde (13a).

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Scheme 4: Modified synthesis of 2-(2-vinylphenyl)acetaldehydes 13a–g and 1-vinyl-2-naphthaldehyde (13h).

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Scheme 5: Lewis acid-catalyzed Prins/Friedel–Crafts reaction of 13a with veratrole.

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Figure 2: The speculated stereostructures of compound cis-14aa and trans-14aa.

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Scheme 6: Use of different nucleophiles for the cascade reaction with 13a. Reaction conditions: a mixture of ...

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Scheme 7: Reaction of aldehydes 13b–h with veratrole or furan. Reaction conditions: a mixture of 13b–h (1.40 ...

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Scheme 8: Synthesis of 5-aryltetrahydro-5H-benzo[7]annulen-7-ols 20a, b.

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Scheme 9: Conversion of 2-hydroxy-4-(2-furyl)tetralin (14af) into PAT analogue 22.

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Figure 3: Crystal structure of the tosylate 21. The displacement ellipsoids are drawn at the 30% probability ...

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Published 22 Jun 2021

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