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

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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 2011

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Propylamines
Heterocyclic Compounds
Methanol
Derivatives

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "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",
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.",
keywords = "3-Alkyl-4-alkyliminopyrimidines, Dimroth rearrangement, nucleophilic aromatic substitution, primary alkylamines, pyrimidin-4(3H)-ones, tandem reactions",
author = "Kensuke Okuda and Hiromi Ohtomo and Tsuyoshi Tagata and Takashi Hirota and Kenji Sasaki",
year = "2011",
month = "1",
doi = "10.1080/00397911003668570",
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pages = "812--819",
journal = "Synthetic Communications",
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T1 - Polycyclic n-heterocyclic compounds, part 68

T2 - 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

AU - Okuda, Kensuke

AU - Ohtomo, Hiromi

AU - Tagata, Tsuyoshi

AU - Hirota, Takashi

AU - Sasaki, Kenji

PY - 2011/1

Y1 - 2011/1

N2 - 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.

AB - 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.

KW - 3-Alkyl-4-alkyliminopyrimidines

KW - Dimroth rearrangement

KW - nucleophilic aromatic substitution

KW - primary alkylamines

KW - pyrimidin-4(3H)-ones

KW - tandem reactions

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