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Reactivity of 7‐(2‐dimethylaminovinyl)pyrazolo[1,5‐ a ]pyrimidines: Synthesis of pyrazolo[1,5‐ a ]pyrido[3,4‐ e ]pyrimidine derivatives as potential benzodiazepine receptor ligands. 1
Author(s) -
Bruni Fabrizio,
Selleri Silvia,
Costanzo Annarella,
Guerrini Gabriella,
Casilli Maria Lucia
Publication year - 1994
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.5570310516
Subject(s) - chemistry , pyrimidine , benzodiazepine , reactivity (psychology) , stereochemistry , combinatorial chemistry , medicinal chemistry , receptor , biochemistry , medicine , alternative medicine , pathology
A series of 7‐methylpyrazolo[1,5‐ a ]pyrimidines were reacted with dimethylformamide dimethylacetal to give the corresponding dimethylaminovinyl derivatives. These were reacted with ammonium acetate affording, through a ring closure, a number of 6‐methylpyrazolo[1,5‐ a ]pyrido[3,4‐ e ]pyrimidines bearing various substituents on the pyrazole ring. The 6‐acetyl‐2‐hydroxy‐7‐methylpyrazolo[1,5‐ a ]pyrimidine was used as starting material for obtaining some O ‐alkyl derivatives. Catalytic transfer hydrogenation of 2‐benzyloxy‐6‐methylpyrazolo[1,5‐ a ]pyrido[3,4‐ e ]pyrimidine led to the 2‐hydroxy derivative.