Direct Access to Highly Functionalised Benzimidazoles and Benzoxazoles from a Common Precursor

Amanda Garrido; Pierre-Olivier Delaye; François Quintin; Mohamed Abarbri; Pedro Lameiras; Alain Gueiffier; Jérôme Thibonnet; Julien Petrignet

doi:10.1055/s-0039-1690153

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(21): 4006-4013
DOI: 10.1055/s-0039-1690153

paper

Direct Access to Highly Functionalised Benzimidazoles and Benzoxazoles from a Common Precursor

Amanda Garrido

^aLaboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France eMail: julien.petrignet@univ-tours.fr

,

Pierre-Olivier Delaye

^aLaboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France eMail: julien.petrignet@univ-tours.fr

,

François Quintin

^aLaboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France eMail: julien.petrignet@univ-tours.fr

,

Mohamed Abarbri

^bLaboratoire Physico-Chimie des Matériaux et des Electrolytes pour l’Energie (PCM2E, EA 6299), Université de Tours, Faculté des Sciences, Parc de Grandmont, 32 Avenue Monge, 37200 Tours, France

,

Pedro Lameiras

^cInstitut de Chimie Moléculaire (ICMR CNRS UMR 7312), UFR Sciences Exactes et Naturelles BP 1039, 51687 Reims, France

,

Alain Gueiffier

^aLaboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France eMail: julien.petrignet@univ-tours.fr

,

Jérôme Thibonnet

^aLaboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France eMail: julien.petrignet@univ-tours.fr

,

Julien Petrignet∗

^aLaboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France eMail: julien.petrignet@univ-tours.fr

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Abstract

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Abstract

Benzoxazole and benzimidazole are commonly encountered heterocycles in medicinal chemistry and their functionalisation around 1-, 2-, 5-, and/or 6-positions provides a wide range of molecules of biological interest. In this manuscript, a straightforward preparation of diversely and highly substituted benzimidazoles and benzoxazoles on these positions, from a common starting material, a 3,3-dibromoacrolein, is described. Such acrolein derivatives are almost never described in the literature or used as ‘building-block’ for organic synthesis. The double electrophilicity of this substrate was found to be advantageous for condensation with two equivalents of various 1,2-diaminobenzene or 2-aminophenol derivatives. This one-pot reaction performed under metal-free and mild conditions allows the creation of three new carbon–heteroatom bonds and affords the desired heterocycles.

Key words

aldehydes - nucleophilic addition - heterocycles - cyclisation - benzimidazoles - benzoxazoles

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Referenzen

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