Polycyclic N-heterocyclic compounds. Part 601): Reactions of 3-(2-cyanophenyl)quinazolin-4(3H)-ones with primary amines

Kensuke Okuda, Tsuyoshi Tagata, Setsuo Kashino, Takashi Hirota, Kenji Sasaki

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The reaction of 3-(2-cyanophenyl)quinazolin-4(3H)-one with various primary alkylamines gave 3-alkylquinazolin-4(3H)-ones via an addition of the nucleophile, ring opening, and ring closure (ANRORC) mechanism. This type of reaction required hydroxy group functionality in either the solvent or reagent. When hydroxylamine was used as nitrogen nucleophile, the intermediate of this reaction was isolated and found to be an amide oxime. When ethylenediamine was used as the nucleophile, the amidine moiety of the intermediate decomposed to give a benzanilide.

Original languageEnglish
Pages (from-to)1296-1299
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume57
Issue number11
DOIs
Publication statusPublished - Nov 2009

Fingerprint

ethylenediamine
Amidines
Heterocyclic Compounds
Nucleophiles
Hydroxylamine
Oximes
Amides
Amines
Nitrogen
4-hydroxyquinazoline
benzanilide

Keywords

  • 3-alkylquinazolin-4(3H)-one
  • Heterocycle
  • Nucleophile addition
  • Primary amine
  • Ring closure
  • Ring opening

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

Polycyclic N-heterocyclic compounds. Part 601) : Reactions of 3-(2-cyanophenyl)quinazolin-4(3H)-ones with primary amines. / Okuda, Kensuke; Tagata, Tsuyoshi; Kashino, Setsuo; Hirota, Takashi; Sasaki, Kenji.

In: Chemical and Pharmaceutical Bulletin, Vol. 57, No. 11, 11.2009, p. 1296-1299.

Research output: Contribution to journalArticle

Okuda, Kensuke ; Tagata, Tsuyoshi ; Kashino, Setsuo ; Hirota, Takashi ; Sasaki, Kenji. / Polycyclic N-heterocyclic compounds. Part 601) : Reactions of 3-(2-cyanophenyl)quinazolin-4(3H)-ones with primary amines. In: Chemical and Pharmaceutical Bulletin. 2009 ; Vol. 57, No. 11. pp. 1296-1299.
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