Polycyclic N-heterocyclic compounds 76: Synthesis and antiplatelet evaluation of 2,4-disubstituted 5,6-Dihydro[1]benzofuro[3′,2′:2,3] oxepino[4,5-d]pyrimidines

Kensuke Okuda, Jun Ichi Takano, Takashi Hirota, Kenji Sasaki, Yuta Nishina, Hiroyuki Ishida

Research output: Contribution to journalArticle

Abstract

Reaction of several Vilsmeier reagents with 5-amino-2,3-dihydro[1] benzofuro[3,2-b]oxepin-4-carbonitrile gave tetracyclic 2-substituted 4-chloro-5,6-dihydro[1]benzofuro[3′,2′:2,3]oxepino[4,5-d] pyrimidines. The structure of one of these, the 4-chloro-2-phenyl derivative, was confirmed by X-ray crystallography. Treatment of the 4-chloro derivatives with simple amines as nucleophile afforded 2-substituted 4-amino derivatives. A pentacyclic compound was also obtained by dehydrative ring closure. These products were evaluated for antiplatelet activity, and some showed potency comparable with that of aspirin.

Original languageEnglish
Pages (from-to)661-668
Number of pages8
JournalJournal of Heterocyclic Chemistry
Volume51
Issue number3
DOIs
Publication statusPublished - May 2014

ASJC Scopus subject areas

  • Organic Chemistry

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