Polycyclic N-heterocyclic compounds, part 77: Synthesis of [1]benzothieno[3',2':2,3]oxepino[4,5-d]pyrimidines and evaluation of their antiplatelet aggregation activity

Kensuke Okuda, Takashi Nikaido, Takashi Hirota, Kenji Sasaki

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Reaction of 3-(3-cyanopropoxy)[1]benzothiophene-2-carbonitrile with sodium hydride gave 5-amino-1,2-dihydro[1]benzothieno[3,2-d]furo[2,3-b]pyridine and 5-amino- 2,3-dihydro[1]benzothieno[3,2-b]oxepin-4-carbonitrile. The latter compound served as a convenient scaffold for the synthesis of the new heterocycles [1]benzothieno[30,20:2, 3]oxepino[4,5-d]pyrimidines and the parent 1,2,4,5-tetrahydro[1]benzothieno[20,30:6, 7]oxepino[4,5-e]imidazo[1,2-c] pyrimidine heterocyclic system. The new compounds described in this report were evaluated as inhibitors of platelet aggregation in vitro. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file.

Original languageEnglish
Pages (from-to)1619-1625
Number of pages7
JournalSynthetic Communications
Volume43
Issue number12
DOIs
Publication statusPublished - 2013

Fingerprint

Oxepins
Heterocyclic Compounds
Pyrimidines
Platelet Aggregation Inhibitors
Scaffolds
Agglomeration
sodium hydride
imidazo(1,2-c)pyrimidine
benzothiophene
furo(3,2-b)pyridine

Keywords

  • Antiplatelet aggregation
  • Cyclization
  • Thorpe-Ziegler reaction
  • Truce-Smiles rearrangement
  • Vilsmeier reagent

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Polycyclic N-heterocyclic compounds, part 77 : Synthesis of [1]benzothieno[3',2':2,3]oxepino[4,5-d]pyrimidines and evaluation of their antiplatelet aggregation activity. / Okuda, Kensuke; Nikaido, Takashi; Hirota, Takashi; Sasaki, Kenji.

In: Synthetic Communications, Vol. 43, No. 12, 2013, p. 1619-1625.

Research output: Contribution to journalArticle

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