The Application of Benziodazole-Type O₂NO-I(III) Compound as a Nitrating Reagent for Nitration of Phenols and Anilines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(6), P. 2328 - 2340

Published: Jan. 31, 2025

A benziodazole-type O2NO-I(III) compound was used as a nitrating reagent to react with series of electron-rich arenes including substituted phenols and anilines, affording the corresponding nitration products under mild conditions. Mechanistically, generates reactive nitrogen dioxide (NO2) species, which enables anilines.

Language: Английский

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Dearomatization of Aromatic Compounds: A Decade Review

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 28, 2025

Abstract Dearomatization offers an efficient strategy for directly converting arenes into cyclic molecules. In this review, we discuss representative examples of dearomatization reactions through five modes: (1) radical dearomatization, (2) halofunctionalization‐dearomatization, in which three‐membered intermediates were frequently involved, (3) nucleophilic mainly about electron‐rich arenes, (4) oxidative and (5) reductive dearomatization. Compared to heteroarenes, simple benzene are more challenging participate reactions. recent years, fewer reports have focused on benzene. Heteroarenes, inherently or easily activated, tend undergo readily. This review highlights a decade progress including indoles, benzofurans, benzothiophenes, thiophenes, furans, naphthols, naphthalenes, quinolines, pyridines, nitrobenzenes, benzenes. It also analyzes their mechanisms strategies. We hope will aid future research field.

Language: Английский

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Preparation of a benziodazole-type iodine(III) compound and its application as a nitrating reagent for synthesis of furazans via a copper-catalyzed cascade process

Communications Chemistry, Journal Year: 2024, Volume and Issue: 7(1)

Published: July 9, 2024

Abstract The existing hypervalent I(III) reagents bearing ONO 2 group are limited in types and their applications primarily focused on the nitrooxylation reactions featuring a fully- exo fashion. Herein, benziodazole-type O NO-I(III) compound was prepared its reaction with β-monosubstituted enamines presence of CuI could trigger radical nitration/cyclization/dehydration cascade to provide series less explored but biologically interesting furazan heterocycles. Mechanistically, acts as nitrating reagent incorporates NO moiety into final product endo model, process which proposed involve nitration, cyclization dehydration.

Language: Английский

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Atom-Efficient Chlorinative Dearomatization of Naphthol, Quinolinol, and Isoquinolinol Derivatives using Trichloroisocyanuric Acid (TCCA)

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 30, 2024

A variety of dearomatized compounds have been prepared in moderate to excellent yields from planar scaffolds using trichloroisocyanuric acid (TCCA) as an atom-economical chlorinating agent. The method tolerates a broad range functionalities and can take place several green and/or sustainable solvents. Twenty-one examples 1,1-dichlorinated products 2-naphthols analogous heteroarenes (quinolinols, isoquinolinols, quinazolinol) are reported along with five monochlorinated products. utility the 1,1-dichloronaphthalenone product reactive intermediate species is demonstrated two-step, one-pot reaction carried out solvent. In mechanistic investigation, coordination agent hydroxy substituent scaffold prior chlorine transfer implicated.

Language: Английский

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