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Polycyclic N ‐Heterocyclic Compounds. Part 84: Reaction of N ‐(pyrido[3′,2′:4,5]thieno[3,2‐ d ]pyrimidin‐4‐yl)amidines or N ‐(pyrido[2′,3′:4,5]furo[3,2‐ d ]pyrimidin‐4‐yl)amidines with Hydroxylamine Hydrochloride
Author(s) -
Okuda Kensuke,
Ide Ryota,
Uramaru Naoto,
Hirota Takashi
Publication year - 2015
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.2033
Subject(s) - chemistry , hydroxylamine hydrochloride , hydroxylamine , ring (chemistry) , formamide , hydrochloride , pyrimidine , amidine , medicinal chemistry , oxadiazole , stereochemistry , organic chemistry
The reactions of nine N ‐(pyrido[3′,2′:4,5]thieno[3,2‐ d ]pyrimidin‐4‐yl)amidines ( 3 ) with hydroxylamine hydrochloride produced new cyclization products. These were formed via ring cleavage of the pyrimidine component followed by a 1,2,4‐oxadiazole‐forming ring closure to give N ‐[2‐([1,2,4]oxadiazol‐5‐yl)thieno[2,3‐ b ]pyridin‐3‐yl]formamide oximes ( 11 ). Reaction of six N ‐(pyrido[2′,3′:4,5]furo[3,2‐ d ]pyrimidin‐4‐yl)amidines ( 12 ) with hydroxylamine hydrochloride gave similar results. Effects of the newly synthesized compounds on pentosidine formation were also evaluated.