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Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents.

ABSTRACT: We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32-98% yield) and pyrimidine derivatives (45-88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et3N).

SUBMITTER: Vitale P

PROVIDER: S-EPMC7418094 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents.

Vitale Paola P Cicco Luciana L Cellamare Ilaria I Perna Filippo M FM Salomone Antonio A Capriati Vito V

Beilstein journal of organic chemistry 20200805

We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32-98% yield) and pyrimidine derivatives (45-88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et<sub>3</sub>N). ...[more]

PMID: 32802208

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