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Addition of 4-(cyclohex-1-en-1-yl)morpholine on 3-nitroindole: An unprecedented dearomatizing process

Abstract : Nucleophilic enamines add spontaneously on heteroarenes 3-nitroindole and benzofuran to form a new C–C bond. With nitroindole (1) and enamine (2a), an unprecedented dearomatizing formal ene reaction occurs in a totally regio- and diastereo-selective manner. With 3-nitrobenzofuran (10) and enamine (2d), the reaction course is different and leads to the generation of a dienylphenol.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046184
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:36:10 PM
Last modification on : Thursday, July 2, 2020 - 3:28:37 AM

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Manuel Andreini, Fabien Chapellas, Sonia Diab, Karine Pasturaud, Serge Piettre, et al.. Addition of 4-(cyclohex-1-en-1-yl)morpholine on 3-nitroindole: An unprecedented dearomatizing process. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2016, 14 (10), pp.2833-2839. ⟨10.1039/c5ob02595h⟩. ⟨hal-02046184⟩

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