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

The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF(3)·Et(2)O 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/F...

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Autores principales: Zheng, Jie, Meng, Shuyu, Wang, Quanrui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8239259/
https://www.ncbi.nlm.nih.gov/pubmed/34239615
http://dx.doi.org/10.3762/bjoc.17.104
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author Zheng, Jie
Meng, Shuyu
Wang, Quanrui
author_facet Zheng, Jie
Meng, Shuyu
Wang, Quanrui
author_sort Zheng, Jie
collection PubMed
description The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF(3)·Et(2)O 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.
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spelling pubmed-82392592021-07-07 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 Meng, Shuyu Wang, Quanrui Beilstein J Org Chem Full Research Paper The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF(3)·Et(2)O 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. Beilstein-Institut 2021-06-22 /pmc/articles/PMC8239259/ /pubmed/34239615 http://dx.doi.org/10.3762/bjoc.17.104 Text en Copyright © 2021, Zheng et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Zheng, Jie
Meng, Shuyu
Wang, Quanrui
Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols
title Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols
title_full Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols
title_fullStr Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols
title_full_unstemmed Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols
title_short Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols
title_sort cascade intramolecular prins/friedel–crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5h-benzo[7]annulen-7-ols
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8239259/
https://www.ncbi.nlm.nih.gov/pubmed/34239615
http://dx.doi.org/10.3762/bjoc.17.104
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AT wangquanrui cascadeintramolecularprinsfriedelcraftscyclizationforthesynthesisof4aryltetralin2olsand5aryltetrahydro5hbenzo7annulen7ols

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