Fe-Catalyzed Hydrocyclizationof Inactivated Alkenesto Synthesize Ring-Fused 2,3-Dihydroquinazolinone

A Fe-catalyzed hydrocyclization reaction of unactivated alkenes was developed, utilizing PhSiH<sub>3</sub> as the hydrogen source, yielding 2,3-dihydroquinazolinone (DHQZ) derivatives in moderate to good yields. Notably, when the substrate was switched to <i>N</i>-cyano-<i>N</i>-(2-(prop-1-en-2-yl)phenyl)benzamides, the reaction yielded only the unreduced products. Mechanistic studies revealed that the intramolecular addition of the in situ formed radical to the unactivated alkene results in the formation of the fused ring.

Publication Details

Journal
Figshare
Published
2025-01-22
DOI
https://doi.org/10.1021/acs.joc.4c02410.s001
Primary Topic
Pediatric Pain Management Techniques
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article
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Fe-Catalyzed Hydrocyclizationof Inactivated Alkenesto Synthesize Ring-Fused 2,3-Dihydroquinazolinone

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Pediatric Pain Management Techniques
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Fe-Catalyzed Hydrocyclizationof Inactivated Alkenesto Synthesize Ring-Fused 2,3-Dihydroquinazolinone

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Abstract

A Fe-catalyzed hydrocyclization reaction of unactivated alkenes was developed, utilizing PhSiH<sub>3</sub> as the hydrogen source, yielding 2,3-dihydroquinazolinone (DHQZ) derivatives in moderate to good yields. Notably, when the substrate was switched to <i>N</i>-cyano-<i>N</i>-(2-(prop-1-en-2-yl)phenyl)benzamides, the reaction yielded only the unreduced products. Mechanistic studies revealed that the intramolecular addition of the in situ formed radical to the unactivated alkene results in the formation of the fused ring.

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Fe-Catalyzed Hydrocyclizationof Inactivated Alkenesto Synthesize Ring-Fused 2,3-Dihydroquinazolinone · Figshare (2025) | TGRS Research Map | TGRS