Synthesis of a Novel 1,4-Dicarbonyl Scaffold – Ethyl 3-Formyl-4,5-dihydrofuran-2-carboxylate – and Its Application to the Synthesis of Pyridazines

Mário A. Marangoni; Paulo A. Moraes; Adriano F. Camargo; Helio G. Bonacorso; Marcos A. P. Martins; Nilo Zanatta

doi:10.1055/s-0039-1690886

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(17): 2528-2534
DOI: 10.1055/s-0039-1690886

paper

Synthesis of a Novel 1,4-Dicarbonyl Scaffold – Ethyl 3-Formyl-4,5-dihydrofuran-2-carboxylate – and Its Application to the Synthesis of Pyridazines

Mário A. Marangoni

,

Paulo A. Moraes

,

Adriano F. Camargo

,

Helio G. Bonacorso

,

Marcos A. P. Martins

,

Nilo Zanatta ∗

Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil eMail: nilo.zanatta@ufsm.br

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Abstract

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Abstract

The 1,4-dicarbonyl scaffold ethyl 3-formyl-4,5-dihydrofuran-2-carboxylate was obtained through the rearrangement of the parent ethyl 2-(4,5-dihydrofuran-3-yl)-2-oxoacetate and applied to the synthesis of a series of 7-alkoxy-2,3-dihydrofuro[2,3-d]pyridazines. Twelve pyridazines were obtained in yields of up to 70%.

Key words

pyridazines - enones - oxoacetates - dihydrofuran - 1,4-dicarbonyl compounds - formyl esters

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