Nitrogen bridgehead compounds. Part 5. Cyclization of 2-(2- pyridylaminomethylene)-succinates and -glutarates

Lelle Vasvári-Debreczy, I. Hermecz, Zoltán Mészáros, Ágnes Horvath, Piroska Simon-Párkányi

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Abstract

A study has been made of the cyclization reactions of some 2-(2-pyridylaminomethylene)-succinates (7) and -glutarates (8) in phosphoryl chloride-polyphosphoric acid. In the cyclization of the succinates (7) we have found that of the possible cyclic products pyrido[1,2-a]pyrimidines (9) and pyridylpyrrolinones (13) are formed, and the latter, subsequently, may form pyridylpyrroles (15) although the reaction conditions favour the formation of pyridopyrimidines (9). The ratio of pyridopyrimidines (9) and pyridylpyrroles [(13):(15)] was independent of the geometry of the starting succinates (7), but was dependent upon the substituent of the pyridine ring, and on its position. Substituents in position 6 hindered the formation of pyridopyrimidines (9) while those in position 3 inhibited the formation of pyridylpyrrolinones (13). From the homologous glutarates (8) only pyrido[1,2-a]pyrimidines (10) are formed.

Original languageEnglish
Pages (from-to)795-799
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number8
Publication statusPublished - 1978

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Succinates
Glutarates
Nitrogen Compounds
Cyclization
Pyrimidines
Geometry

ASJC Scopus subject areas

  • Chemistry(all)

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Nitrogen bridgehead compounds. Part 5. Cyclization of 2-(2- pyridylaminomethylene)-succinates and -glutarates. / Vasvári-Debreczy, Lelle; Hermecz, I.; Mészáros, Zoltán; Horvath, Ágnes; Simon-Párkányi, Piroska.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 8, 1978, p. 795-799.

Research output: Contribution to journalArticle

Vasvári-Debreczy, Lelle ; Hermecz, I. ; Mészáros, Zoltán ; Horvath, Ágnes ; Simon-Párkányi, Piroska. / Nitrogen bridgehead compounds. Part 5. Cyclization of 2-(2- pyridylaminomethylene)-succinates and -glutarates. In: Journal of the Chemical Society, Perkin Transactions 1. 1978 ; No. 8. pp. 795-799.
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AU - Horvath, Ágnes

AU - Simon-Párkányi, Piroska

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