Reaction of Spiro[piperidine-4,2′-(1′,2′,3′,4′-tetrahydroquinazolin)]-4′-ones with Acid Anhydrides

Masatoshi Yamato, Jiroh Horiuchi, Yasuo Takeuchi

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Acylation of spiro[piperidine-4, 2′-(1′, 2′, 3′, 4′-tetrahydroquinazolin)]-4′-ones (1d, 4, 6, and 7) was attempted. In all cases, the resulting products were not the corresponding acyl derivatives but two types of products (2 or 3 and 5). Heating 1d, the derivative having hydrogen atoms on the N(1) and N(3)-positions of spiro[piperidine-4, 2′-(1′, 2′, 3′, 4′-tetrahydroquinazolin)]-4′-ones with acetic anhydride or benzoic anhydride gave 1-(1-benzyl-1, 2, 5, 6-tetrahydro-4-pyridyl)-2-methyl-1, 4-dihydroquinazolin-4-one (2) or 1-(1-benzyl-1, 2, 5, 6-tetrahydro-4-pyridyl)-2-phenyl-1, 4-dihydroquinazolin-4-one (3), respectively. On the other hand, heating 4, the N(1)-substituted derivative of 1d, with acetic anhydride gave 2-benzyl-5-methyl-1, 2, 3, 4, 5, 10-hexahydro-benzo[b]-1, 6-naphthyridin-10-one (5). The N(3)-substituted derivatives (6 and 7) of 1d did not react with acetic anhydride.

Original languageEnglish
Pages (from-to)2623-2628
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume28
Issue number9
DOIs
Publication statusPublished - Jan 1 1980

Keywords

  • 1,6-naphthyridine
  • C-NMR
  • quinazoline
  • reaction mechanism
  • reaction with acid anhydride
  • rearrangement

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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