Nitrogen bridgehead compounds. Part 6. Ring transformation. Part 3. Thermal cyclization of diethyl 2-(2-pyridylaminomethylene)-succinates and -glutarates

Lelle Vasvári-Debreczy, I. Hermecz, Zoltán Mészáros, Péter Dvortsák, Gábor Tóth

Research output: Contribution to journalArticle

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Abstract

The pyridylsuccinates (1) and pyridylglutarates (2), with various substituents on the pyridine ring, were cyclized in Dowtherm A at 250 °C. The succinates cyclized in two competing reaction routes, giving rise to pyrido[1,2-a]-pyrimidines (route A) and N-pyridylpyrrolinones (route B). The ratio of the two products varied with the nature of the substituent and its position. The N-pyridylpyrrolinones proved to be mixtures of the desmotropes (5) and (6) which were separated. The pyridylglutarates (2) gave only the pyrido[1,2-a]pyrimidines (4). The 6-substituted pyrido[1,2-a]pyrimidines underwent a ring-transformation reaction at or above 250 °C, forming the corresponding 1,8-naphthyridines (8) and (9).

Original languageEnglish
Pages (from-to)227-232
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1980

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Succinates
Glutarates
Nitrogen Compounds
Pyrimidines
Cyclization
Naphthyridines
Hot Temperature

ASJC Scopus subject areas

  • Chemistry(all)

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Nitrogen bridgehead compounds. Part 6. Ring transformation. Part 3. Thermal cyclization of diethyl 2-(2-pyridylaminomethylene)-succinates and -glutarates. / Vasvári-Debreczy, Lelle; Hermecz, I.; Mészáros, Zoltán; Dvortsák, Péter; Tóth, Gábor.

In: Journal of the Chemical Society, Perkin Transactions 1, 1980, p. 227-232.

Research output: Contribution to journalArticle

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AU - Vasvári-Debreczy, Lelle

AU - Hermecz, I.

AU - Mészáros, Zoltán

AU - Dvortsák, Péter

AU - Tóth, Gábor

PY - 1980

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N2 - The pyridylsuccinates (1) and pyridylglutarates (2), with various substituents on the pyridine ring, were cyclized in Dowtherm A at 250 °C. The succinates cyclized in two competing reaction routes, giving rise to pyrido[1,2-a]-pyrimidines (route A) and N-pyridylpyrrolinones (route B). The ratio of the two products varied with the nature of the substituent and its position. The N-pyridylpyrrolinones proved to be mixtures of the desmotropes (5) and (6) which were separated. The pyridylglutarates (2) gave only the pyrido[1,2-a]pyrimidines (4). The 6-substituted pyrido[1,2-a]pyrimidines underwent a ring-transformation reaction at or above 250 °C, forming the corresponding 1,8-naphthyridines (8) and (9).

AB - The pyridylsuccinates (1) and pyridylglutarates (2), with various substituents on the pyridine ring, were cyclized in Dowtherm A at 250 °C. The succinates cyclized in two competing reaction routes, giving rise to pyrido[1,2-a]-pyrimidines (route A) and N-pyridylpyrrolinones (route B). The ratio of the two products varied with the nature of the substituent and its position. The N-pyridylpyrrolinones proved to be mixtures of the desmotropes (5) and (6) which were separated. The pyridylglutarates (2) gave only the pyrido[1,2-a]pyrimidines (4). The 6-substituted pyrido[1,2-a]pyrimidines underwent a ring-transformation reaction at or above 250 °C, forming the corresponding 1,8-naphthyridines (8) and (9).

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