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Aromaticity in heterocyclic systems V. Bromination studies of certain purines, pyrrolo[3,2‐ d ]pyrimidines and pyrazolo[4,3‐ d ]pyrimidines
Author(s) -
Cassidy Frederick,
Olsen Richard K.,
Robins Roland K.
Publication year - 1968
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.5570050404
Subject(s) - chemistry , halogenation , bromine , purine metabolism , reactivity (psychology) , xanthine , bicyclic molecule , stereochemistry , aromaticity , medicinal chemistry , organic chemistry , molecule , pathology , medicine , alternative medicine , enzyme
The bromination of certain selected purines, pyrrolo[3,2‐d]pyrimidines and pyrazolo[4,3‐ d ]‐pyrimidines has been studied and the reactivity of these systems compared. Displacement of a carboxyl group by bromine was noted in the case of 6‐carboxypyrrolo[3,2‐ d ]‐2,4‐pyrimidinedione. In contrast to xanthine, 2,6‐diethoxypurine readily brominated at position 8. Pyrazolo‐[4,3‐ d ]‐7‐pyrimidone was readily brominated at position 3.