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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
Author(s) -
Okuda Kensuke,
Takano Junichi,
Hirota Takashi,
Sasaki Kenji,
Nishina Yuta,
Ishida Hiroyuki
Publication year - 2014
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1539
Subject(s) - chemistry , ring (chemistry) , nucleophile , reagent , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , financial economics , economics
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.