Ruthenium-Catalyzed C(3)-H Alkylation of the Furan (Thiophene) Ring of 2-Furoyl- and Thiophene-2-carbonyl-1-methylimidazoles with Acrylic Acid Derivatives

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Resumo

A method for the synthesis of 3-alkyl-2-furoyl- and thiophene-2-carbonyl-1-methylimidazoles by ruthenium-catalyzed selective C(3)-H alkylation of the furan (thiophene) ring 2-furoyl(thiophene-2-carbonyl)-1-methylimidazoles with esters, amides or nitrile of acrylic acid has been developed. The resulting compounds may be of interest as polyfunctional reagents or for the preparation of 3-(2-carboxyethyl)furan(thiophene)2-carboxylic acid derivatives.

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Sobre autores

K. Shepelenko

Platov South-Russian State Polytechnic University (NPI)

Autor responsável pela correspondência
Email: kon1990@bk.ru
ORCID ID: 0000-0002-7281-5095
Rússia, Prosveschenya, 132, Novocherkassk, 346428

I. Gnatiuk

Platov South-Russian State Polytechnic University (NPI)

Email: kon1990@bk.ru
ORCID ID: 0009-0003-8772-6372
Rússia, Prosveschenya, 132, Novocherkassk, 346428

V. Chernyshev

Platov South-Russian State Polytechnic University (NPI)

Email: chern13@yandex.ru
ORCID ID: 0000-0001-9182-8564
Rússia, Prosveschenya, 132, Novocherkassk, 346428

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2. Fig. Diagram of key correlations in the 1H–1H NOESY spectra of compounds 3b.

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3. Scheme 1 Reagents and conditions: compound 1a (0.1 mmol), butyl acrylate (0.2–0.5 mmol), [RuCl2(p-cymene)]2 (0.005–0.015 mmol), base (0.2 mmol), solvent 1 ml, 20 h.

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4. Scheme 2 Reagents and conditions: i: compound 1a,b (0.25 mmol), alkene (1 mmol), [RuCl2(p-cymene)]2 (0.025mmol), KOAc (0.5 mmol), 1,4-dioxane 2 ml, 110C, 16 h.

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5. Scheme 3 Reagents and conditions: i: compound 3a (0.1 mmol), MeI (1 mmol), 1,4-dioxane (1 ml), 110c, 2 hours ii: 4 (0.1 mmol), 1 n.o. NaOH solution (1 ml), 2 hours, 25c, then 1 n. HCl solution, 2 hours, 25s.

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6. Ruthenium-catalyzed C(3)–H alkylation of the furan (thiophene) core 2-furoyl- and thiophene-2-carbonyl-1-methylimidazole derivatives of acrylic acid

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