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 journalArticlepeer-review

    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 - Apr 22 2013

    Keywords

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

    ASJC Scopus subject areas

    • Organic Chemistry

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