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Electrochemical Iodine-Mediated Oxidation of Enamino-Esters to 2H-Azirine-2-Carboxylates Supported by Design of Experiments.

ABSTRACT: An electrochemical iodine-mediated transformation of enamino-esters for the synthesis of 2H-azirine-2-carboxylates is presented. In addition, a thermic conversion of azirines to 4-carboxy-oxazoles in quantitative yield without purification was described. Both classes 2H-azirines-2-carboxylates and the 4-carboxy-oxazoles are substructures in natural products and therefore are of considerable interest for synthetic and pharmaceutical chemists. The optimization was not performed in a conventional manner with a one-factor-at-a-time process but with a Design of Experiments (DoE) approach. Beside a broad substrate scope the reaction was also employed to a robustness screen, a sensitivity assessment, and complemented with mechanistic considerations from cyclic voltammetry experiments.

SUBMITTER: Babaoglu E

PROVIDER: S-EPMC7497194 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Electrochemical Iodine-Mediated Oxidation of Enamino-Esters to 2H-Azirine-2-Carboxylates Supported by Design of Experiments.

Babaoglu Emre E Hilt Gerhard G

Chemistry (Weinheim an der Bergstrasse, Germany) 20200714 41

An electrochemical iodine-mediated transformation of enamino-esters for the synthesis of 2H-azirine-2-carboxylates is presented. In addition, a thermic conversion of azirines to 4-carboxy-oxazoles in quantitative yield without purification was described. Both classes 2H-azirines-2-carboxylates and the 4-carboxy-oxazoles are substructures in natural products and therefore are of considerable interest for synthetic and pharmaceutical chemists. The optimization was not performed in a conventional m ...[more]

PMID: 32220135

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