Photoredox/HAT-Catalyzed\nIntramolecular Hydrocyclization\nof Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones

New photochemical approaches to 2,3-fused quinazolinones\nand dihydroquinazolinones\nare disclosed. The intramolecular hydrocyclization proceeds in moderate\nto excellent yields across diverse alkenes with high regioselectivity\nand diastereocontrol. Mechanistic studies indicated that the radical\ncascade processes involve thiophenol acting as single-electron transfer\nand hydrogen atom transfer reagents. The success of the gram-scale\nsynthesis proves the strategy can be used for practical applications.

Publication Details

Journal
Figshare
Published
2024-10-02
DOI
https://doi.org/10.1021/acs.orglett.4c02974.s001
Primary Topic
Genetic Mapping and Diversity in Plants and Animals
Type
article
Field-Weighted Citation Impact
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Photoredox/HAT-Catalyzed\nIntramolecular Hydrocyclization\nof Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones

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Genetic Mapping and Diversity in Plants and Animals
article

Photoredox/HAT-Catalyzed\nIntramolecular Hydrocyclization\nof Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones

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Abstract

New photochemical approaches to 2,3-fused quinazolinones\nand dihydroquinazolinones\nare disclosed. The intramolecular hydrocyclization proceeds in moderate\nto excellent yields across diverse alkenes with high regioselectivity\nand diastereocontrol. Mechanistic studies indicated that the radical\ncascade processes involve thiophenol acting as single-electron transfer\nand hydrogen atom transfer reagents. The success of the gram-scale\nsynthesis proves the strategy can be used for practical applications.

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Openalex Percentile: Top 49%
Genetic Mapping and Diversity in Plants and Animals
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Photoredox/HAT-Catalyzed\nIntramolecular Hydrocyclization\nof Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones · Figshare (2024) | TGRS Research Map | TGRS