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Polycyclic N ‐Heterocyclic Compounds. Part 81: Synthesis and Evaluation of Pentacyclic 1,2,4,5‐Tetrahydro[1]benzothieno[2′,3′:6,7]thiepino[4,5‐ e ]imidazo[1,2‐ c ]pyrimidine and Related Compounds as Potential Antiplatelet Aggregators
Author(s) -
Okuda Kensuke,
Itzuji Yutaka,
Hirota Takashi
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.1754
Subject(s) - chemistry , derivative (finance) , pyrimidine , ring (chemistry) , stereochemistry , chloride , closure (psychology) , medicinal chemistry , phosphoryl chloride , organic chemistry , financial economics , economics , market economy
Dehydrative ring closure reactions were carried out on fused 4‐(2‐hydroxyethylamino) (or 2‐hydroxyethoxy or 2‐hydroxyethylthio)pyrimidines ( 2a , 2b , 2c ) to give fused 2,3‐dihydroimidazo[1,2‐ c ] (or 2,3‐dihydrooxazolo[3,2‐ c ] or 2,3‐dihydrothiazolo[3,2‐ c ])pyrimidines. This reaction produced the pentacyclic 1,2,4,5‐tetrahydro[1]benzothieno[2′,3′:6,7]thiepino[4,5‐ e ]imidazo[1,2‐ c ]pyrimidine ( 3a ) and 1,2,4,5‐tetrahydro[1]benzothieno[2′,3′:6,7]thiepino[4,5‐ e ]thiazolo[3,2‐ c ]pyrimidinium chloride ( 3c ) from the 2‐hydroxyethylamino‐derivative and 2‐hydroxyethylthio‐derivative, respectively. In contrast, 2‐hydroxyethoxy‐derivative ( 2b ) gave the rearrangement product, 3‐(2‐chloroethyl)‐5,6‐dihydro[1]benzothieno[3′,2′:2,3]thiepino[4,5‐ d ]pyrimidin‐4(3 H )‐one ( 4 ). Effects of the synthesized compounds on collagen‐induced platelet aggregation were also evaluated.