1,1′-Diarylethylene\nas a Key Additive for the\nVisible Light Synthesis of Bioactive Dihydrobenzo[<i>a</i>]phenanthridine Compounds

This\nstudy introduces a straightforward synthetic approach for\ngenerating 7,8-dihydrobenzo[<i>a</i>]phenanthridine analogs\nthrough visible-light-induced cyclization, showing promise as antitumor\nagents. Unexpectedly, the incorporation of 1,1′-diarylethylene\nas an additive significantly boosts yield. Through mechanistic investigations,\nwe uncover its crucial role as a trap for the methyl radical formed\nafter the N–O bond cleavage of <i>O-</i>acetyl oxime,\npromoting intramolecular cyclization of a nitrogen-centered imine\nradical. These insights into the mechanism pave the way for transformative\nadvancements in this synthesis strategy.

Publication Details

Journal
Figshare
Published
2024-10-01
DOI
https://doi.org/10.1021/acs.joc.4c01891.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

1,1′-Diarylethylene\nas a Key Additive for the\nVisible Light Synthesis of Bioactive Dihydrobenzo[a]phenanthridine Compounds

Figshare
Radical Photochemical Reactions
article

1,1′-Diarylethylene\nas a Key Additive for the\nVisible Light Synthesis of Bioactive Dihydrobenzo[a]phenanthridine Compounds

article en

Abstract

This\nstudy introduces a straightforward synthetic approach for\ngenerating 7,8-dihydrobenzo[<i>a</i>]phenanthridine analogs\nthrough visible-light-induced cyclization, showing promise as antitumor\nagents. Unexpectedly, the incorporation of 1,1′-diarylethylene\nas an additive significantly boosts yield. Through mechanistic investigations,\nwe uncover its crucial role as a trap for the methyl radical formed\nafter the N–O bond cleavage of <i>O-</i>acetyl oxime,\npromoting intramolecular cyclization of a nitrogen-centered imine\nradical. These insights into the mechanism pave the way for transformative\nadvancements in this synthesis strategy.

Figshare
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Radical Photochemical Reactions
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1,1′-Diarylethylene\nas a Key Additive for the\nVisible Light Synthesis of Bioactive Dihydrobenzo[<i>a</i>]phenanthridine Compounds · Figshare (2024) | TGRS Research Map | TGRS