Nitrogen bridgehead compounds. Part 4. 1 → 3N → C-acyl migration. Part 2

István Hermecz, Zoltán Mészáros, Lelle Vasvári-Debreczy, Ágnes Horváth, Gábor Horváth, Mariann Pongor-Csákvári

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Abstract

Ring closure of 2-substituted 3-(2-pyridylamino)acrylates (1) in phosphoryl chloride-polyphosphoric acid gives pyrido[1,2-a]pyrimidines (2), whereas (6-substituted 2-pyridyl) derivatives in Dowtherm A afford pyrido[1,2-a]- pyrimidines (2) and 1,8-naphthyridines (3). The 6-substituted pyrido[1,2-a]pyrimidines (2) can be converted thermally into 1,8-naphthyridines (3) by 1 → 3 N → C-acyl migration. Similar acyl migrations can be observed in other such systems.

Original languageEnglish
Pages (from-to)789-795
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
DOIs
Publication statusPublished - 1977

ASJC Scopus subject areas

  • Chemistry(all)

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    Hermecz, I., Mészáros, Z., Vasvári-Debreczy, L., Horváth, Á., Horváth, G., & Pongor-Csákvári, M. (1977). Nitrogen bridgehead compounds. Part 4. 1 → 3N → C-acyl migration. Part 2. Journal of the Chemical Society, Perkin Transactions 1, (7), 789-795. https://doi.org/10.1039/p19770000789