Polycyclic n-heterocyclic compounds, part 68: Reactions of 3-(2-bromoethyl)quinazolin-4(3H)-one and 3-(2-bromoethyl)-5,6,7,8- tetrahydroquinazolin-4(3H)-one with primary alkylamines via a dimroth-type rearrangement

Kensuke Okuda, Hiromi Ohtomo, Tsuyoshi Tagata, Takashi Hirota, Kenji Sasaki

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The reaction of 3-(2-bromoethyl)quinazolin-4(3H)-one with ethyl- and n-propylamine gave abnormal fused 3-alkyl-4-alkyliminoquinazolines via a Dimroth-type rearrangement, as well as normal substituted 3-(2-alkylaminoethyl) derivatives in methanol. The reaction of 3-(2-bromoethyl)-5,6,7,8- tetrahydroquinazolin-4(3H)-one with primary alkylamines was also investigated for the scope of this rearrangement reaction.

Original languageEnglish
Pages (from-to)812-819
Number of pages8
JournalSynthetic Communications
Volume41
Issue number6
DOIs
Publication statusPublished - Jan 1 2011

Keywords

  • 3-Alkyl-4-alkyliminopyrimidines
  • Dimroth rearrangement
  • nucleophilic aromatic substitution
  • primary alkylamines
  • pyrimidin-4(3H)-ones
  • tandem reactions

ASJC Scopus subject areas

  • Organic Chemistry

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