ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Electrochemical Iodine-Mediated Oxidation of Enamino-Esters to 2H-Azirine-2-Carboxylates Supported by Design of Experiments.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 39 citations in OpenAlex.
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- Easy Access to Fused Tricyclic Quinoline Derivatives through Metal-Free Electrocatalytic [4 + 2] Annulation.ACS organic & inorganic Au · 2024Article
- Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates.Beilstein journal of organic chemistry · 2024Article
- Working at the interfaces of data science and synthetic electrochemistry.Tetrahedron chem · 2022Article
- Indium-Catalysed Transfer Hydrogenation for the Reductive Cyclisation of 2-Alkynyl Enones towards Trisubstituted Furans.Angewandte Chemie (International ed. in English) · 2021Article
- Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels-Alder Reactions.Angewandte Chemie (International ed. in English) · 2021Article
- New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry.ACS central science · 2020Review
- Electrochemical Iodine-Mediated Oxidation of Enamino-Esters to 2H-Azirine-2-Carboxylates Supported by Design of Experiments.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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2 authors at 1 institution in 1 country.
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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.
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