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Utilization of cleavage of the [1]benzofuro[2,3‐ e ][1,2,4]triazine ring for the synthesis of oxygen, nitrogen and sulfur derivatives of [1,2,4]triazine
Author(s) -
Stýskala Jakub,
Slouka Jan,
Wiedermannová Iveta,
Bednář Petr
Publication year - 2003
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.5570400509
Subject(s) - chemistry , triazine , selenide , nucleophile , ring (chemistry) , medicinal chemistry , cleavage (geology) , furan , sulfur , hydrogen sulfide , nitrogen , derivative (finance) , 1,3,5 triazine , stereochemistry , organic chemistry , selenium , catalysis , geotechnical engineering , fracture (geology) , financial economics , engineering , economics
Abstract A series of 6‐azacytosines 4a‐4k and 5a‐5c were prepared by nucleophilic cleavage of furan ring of [1]benzofuro[2,3‐ e ][1,2,4]triazine derivative 1 . Some of them were used for the preparation of derivatives of [1,2,4]triazolo[4,3‐ d ][1,2,4]triazine ( 6a‐6d ) and tetrazolo[1,5‐ d ][1,2,4]triazine (7). The reaction of 1 with hydrogen sulfide afforded the corresponding 6‐(2‐hydroxyphenyl)‐2‐phenyl‐5‐thioxo‐4,5‐dihydro‐1,2,4‐tri‐azin‐3(2 H )‐one ( 8 ), while with hydrogen selenide 6‐(2‐hydroxyphenyl)‐2‐phenyl‐4,5‐dihydro‐1,2,4‐triazin‐3(2 H )‐one ( 9 ) was formed. The prepared compounds were tested for biological activity.