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The synthesis and chemical reactions of certain pyrazolo[1,5‐ a ]‐1,3,5‐triazines
Author(s) -
Kobe Jože,
Robins Roland K.,
O'Brien Darrell E.
Publication year - 1974
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.5570110217
Subject(s) - chemistry , ring (chemistry) , nucleophile , triazine , hypoxanthine , electrophile , stereochemistry , xanthine , nucleophilic substitution , medicinal chemistry , combinatorial chemistry , organic chemistry , enzyme , catalysis
3‐Aminopyrazole was utilized as a starting material for the preparation of certain pyrazolo‐[1,5‐ a ]‐1,3,5‐triazines. 4‐Chloro‐2‐methylthiopyrazolo[1,5‐ a ]‐1,3,5‐triazine was prepared and used for studies of nucleophilic displacement reactions, and it has been found that both the chloro and methylthio groups may be displaced by nucleophiles. By modifications of these procedures we have prepared the adenine, hypoxanthine, and xanthine analogs of the pyrazolo‐[1,5‐ a ]‐1,3,5‐triazine ring system. Electrophilic substitution occurs in the 8‐position of this ring system. The methyl group was introduced into the 4‐position by a novel ring opening and ring closing of the 1,3,5‐triazine ring.