Journal ArticleDOI
Reactions of N‐Acylated Indoles with Singlet Oxygen.
Reads0
Chats0
TLDR
In this paper, the reaction of seven N-acyl indole derivatives with singlet oxygen was investigated and the results showed that 1-acetyl-(2a) and 1-(chloroacetyl)-2-hydroperoxy-3-methyleneindoline (2b) gave high yields via ene reaction on irradiation with oxygen in the presence of TPP sensitizer.Abstract:
Reactions of seven N-acyl indole derivatives with singlet oxygen have been investigated. 1-Acetyl-(1a) and 1-(chloroacetyl)-2,3-dimethylindole (1b) gave exclusively 1-acetyl-(2a) and 1-(chloroacetyl)-2-hydroperoxy-3-methyleneindoline (2b), respectively, in high yields via ene reaction on irradiation with oxygen in the presence of TPP sensitizer. 1-Acetyl-3-methylindole (1c) gave only 1-acetyl-2-hydroperoxy-3-methyleneindoline (2c) in low yield under the same conditionsread more
Citations
More filters
Journal ArticleDOI
Tryptophan oxidation by singlet molecular oxygen [O2(1Deltag)]: mechanistic studies using 18O-labeled hydroperoxides, mass spectrometry, and light emission measurements.
Graziella E. Ronsein,Mauricio César Bof de Oliveira,Sayuri Miyamoto,Marisa Helena Gennari de Medeiros,Paolo Di Mascio +4 more
TL;DR: In this study, two cis- and trans-tryptophan hydroperoxide (WOOH) isomers were completely characterized by HPLC/mass spectrometry and NMR analyses as the major W-oxidation photoproducts and underwent thermal decay into the corresponding alcohols, indicating a dioxetane cleavage pathway.
Journal ArticleDOI
Mechanism of dioxindolylalanine formation by singlet molecular oxygen-mediated oxidation of tryptophan residues
Graziella E. Ronsein,Mauricio César Bof de Oliveira,Marisa Helena Gennari de Medeiros,Paolo Di Mascio +3 more
TL;DR: Mechanistic investigations based on isotopic labeling and MS/MS analyses support diOia formation through a dioxetane intermediate.
Journal ArticleDOI
Photochemical oxidation of N,N-bis- (tert-butoxycarbonyl)-1,4-dihydropyrazine derivatives
TL;DR: In this article, the photochemical oxidation of N,N-Bis-(tert-butoxycarbonyl)-1,4-dihydropyrazines was investigated by irradiation using a medium-pressure mercury lamp.
References
More filters
Journal ArticleDOI
Reactions of N-acylated indoles with singlet oxygen
TL;DR: In this paper, the reaction of seven N-acyl indole derivatives with singlet oxygen was investigated and the results showed that 1-acetyl-(2a) and 1-(chloroacetyl)-2-hydroperoxy-3-methyleneindoline (2b) gave high yields via ene reaction on irradiation with oxygen in the presence of TPP sensitizer.