Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. IV

Jiroh Horiuchi, Yasuo Takeuchi, Masatoshi Yamato

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The reaction of 2-substituted 1-methyl-1,2,3,4-tetrahydroquinazolin-4-ones (THQ) with acetic anhydride afforded two types of products depending on the number of C2-substituents. The reaction of 2-monosubstituted 1-methyl-THQ (6) gave the corresponding N3-acetyl-THQ derivatives (7), while the reaction of 2,2-disubstituted 1-methyl-THQ (8) afforded rearranged products, 2,3-disubstituted 1-methyl-1,4-dihydroquinolin-4-ones (9). A mechanism is proposed for the reaction of 8 to give 9.

Original languageEnglish
Pages (from-to)3130-3133
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume29
Issue number11
DOIs
Publication statusPublished - Jan 1 1981

Keywords

  • 1,2,3,4-tetrahydroquinazolin-4-ones
  • 1,4-dihydroquinolin-4-ones
  • acetic anhydride
  • acetylation
  • rearrangement

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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