Dearomative\nTransformation of Pyridin-3-ols into 2,3,6,7-Tetrahydro‑1<i>H</i>‑2,6-methanobenzo[<i>d</i>]azonin-12-ones\nvia Oxidopyridinium/<i>o</i>‑Quinodimethane (5 +\n4) Cycloaddition

We report the dearomative transformation of pyridin-3-ols\nvia oxidopyridinium\n(5 + 4) cycloaddition with <i>o</i>-quinodimethanes, leading\nto 2,3,6,7-tetrahydro-1<i>H</i>-2,6-methanobenzo[<i>d</i>]azonin-12-ones. The chemoselective derivatization of the\nobtained cycloadduct was also investigated to demonstrate the synthetic\npotential of the obtained cycloadduct.

Publication Details

Journal
Figshare
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.orglett.4c03878.s001
Primary Topic
Synthesis of Organic Compounds
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article
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Dearomative\nTransformation of Pyridin-3-ols into 2,3,6,7-Tetrahydro‑1H‑2,6-methanobenzo[d]azonin-12-ones\nvia Oxidopyridinium/o‑Quinodimethane (5 +\n4) Cycloaddition

Figshare
Synthesis of Organic Compounds
article

Dearomative\nTransformation of Pyridin-3-ols into 2,3,6,7-Tetrahydro‑1H‑2,6-methanobenzo[d]azonin-12-ones\nvia Oxidopyridinium/o‑Quinodimethane (5 +\n4) Cycloaddition

article en

Abstract

We report the dearomative transformation of pyridin-3-ols\nvia oxidopyridinium\n(5 + 4) cycloaddition with <i>o</i>-quinodimethanes, leading\nto 2,3,6,7-tetrahydro-1<i>H</i>-2,6-methanobenzo[<i>d</i>]azonin-12-ones. The chemoselective derivatization of the\nobtained cycloadduct was also investigated to demonstrate the synthetic\npotential of the obtained cycloadduct.

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Synthesis of Organic Compounds
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Dearomative\nTransformation of Pyridin-3-ols into 2,3,6,7-Tetrahydro‑1<i>H</i>‑2,6-methanobenzo[<i>d</i>]azonin-12-ones\nvia Oxidopyridinium/<i>o</i>‑Quinodimethane (5 +\n4) Cycloaddition · Figshare (2024) | TGRS Research Map | TGRS