ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
One Step Synthesis of 4,6,8-Trimethoxyazulenes - as Building Block for 2-Functionalized Azulenes.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Lewis Acid-Catalyzed Alkylation of Azulene Derivatives with Epoxides and Oxetanes: A Regioselective Approach to Functionalized Azulene Alcohols.Organic letters · 2025Article
- Rhodium-Catalyzed Intermolecular Arylative [2 + 2 + 1] Annulation-Oxidation to Produce Electron-Deficient Azulene-Embedded Polycyclic Aromatic Hydrocarbons.Angewandte Chemie (International ed. in English) · 2025Article
- One Step Synthesis of 4,6,8-Trimethoxyazulenes - as Building Block for 2-Functionalized Azulenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
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Abstract
Here we present a simple gold-catalyzed one-pot reaction of easily available diarylbutadiynes, with trimethoxybenzene as solvent and reactant to synthesize 4,6,8-trimethoxyazulenes. The methoxy substituents, which render the azulene very electron-rich, enable a change of azulenes typical regioselectivity for electrophilic substitutions, which enables facile electrophilic 2-substitution with iodine, bromine, chlorine, selenium or sulfur. Especially the 2-haloazulenes which can usually only be obtained through lengthy multistep syntheses are valuable building blocks for the synthesis of 2-substituted azulene derivatives.
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