Novel rearrangement of an isoxazole to a pyrrole. X-ray molecular structure of diethyl 5-(ethoxycarbonylmethyl)pyrrole-2,4-dicarboxylate

Gábor Doleschall, Péter Seres, L. Párkányí, Gábor Tóth, Atilla Almásy, Éva Bihátsi-Karsai

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Abstract

A basic and novel example of mononuclear heterocyclic rearrangement, the isoxazole-pyrrole conversion, was realized by the rearrangement of diethyl 2-(4-ethoxycarbonyl-5-methylisoxazol-3-yl)glutaconate to diethyl 5-(1-ethoxycarbonyl-2-oxopropyl)pyrrole-2,4-dicarboxylate. An ethoxy-migration was observed in the condensation reaction of 7-ethoxymethylene-6,7-dihydroxy-3- methylpyrano[4,3-c]isoxazole-4,6(7H)-dione with diethyl malonate.

Original languageEnglish
Pages (from-to)927-932
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1986

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Isoxazoles
Pyrroles
Molecular structure
X rays
Condensation reactions
glutaconic acid
diethyl malonate

ASJC Scopus subject areas

  • Chemistry(all)

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Novel rearrangement of an isoxazole to a pyrrole. X-ray molecular structure of diethyl 5-(ethoxycarbonylmethyl)pyrrole-2,4-dicarboxylate. / Doleschall, Gábor; Seres, Péter; Párkányí, L.; Tóth, Gábor; Almásy, Atilla; Bihátsi-Karsai, Éva.

In: Journal of the Chemical Society, Perkin Transactions 1, 1986, p. 927-932.

Research output: Contribution to journalArticle

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abstract = "A basic and novel example of mononuclear heterocyclic rearrangement, the isoxazole-pyrrole conversion, was realized by the rearrangement of diethyl 2-(4-ethoxycarbonyl-5-methylisoxazol-3-yl)glutaconate to diethyl 5-(1-ethoxycarbonyl-2-oxopropyl)pyrrole-2,4-dicarboxylate. An ethoxy-migration was observed in the condensation reaction of 7-ethoxymethylene-6,7-dihydroxy-3- methylpyrano[4,3-c]isoxazole-4,6(7H)-dione with diethyl malonate.",
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AU - Seres, Péter

AU - Párkányí, L.

AU - Tóth, Gábor

AU - Almásy, Atilla

AU - Bihátsi-Karsai, Éva

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