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Journal Articles Synthesis: Journal of Synthetic Organic Chemistry Year : 2019

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

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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.
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Dates and versions

hal-03533721 , version 1 (18-01-2022)

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Amanda Garrido, Pierre-Olivier Delaye, François Quintin, Mohamed Abarbri, Pedro Lameiras, et al.. Direct Access to Highly Functionalised Benzimidazoles and Benzoxazoles from a Common Precursor. Synthesis: Journal of Synthetic Organic Chemistry, 2019, 51 (21), pp.4006-4013. ⟨10.1055/s-0039-1690153⟩. ⟨hal-03533721⟩
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