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Synthesis of 1,3‐dialkylpyrazolo [1,5‐ a ]‐1,3,5‐triazine‐2,4‐diones isomers of 1,3‐dialkylxanthines
Author(s) -
Senga Keitaro,
Kobe Joze,
Robins Roland K.,
O'Brien Darrell E.
Publication year - 1975
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.5570120516
Subject(s) - chemistry , triazine , isothiocyanate , nitrogen atom , halogenation , methyl iodide , iodide , medicinal chemistry , alkyl , 1,3,5 triazine , organic chemistry
The synthesis of a new series of alkylxanthine analogs containing a bridgehead nitrogen atom is reported. 1,3‐Dialkylpyrazolo[1,5‐ a ]‐1,3,5‐triazine‐2,4‐diones, were prepared by the treatment of 3‐methylpyrazolo[1,5‐ a ]‐1,3,5‐triazine‐2,4‐dione (3) with the corresponding alkyl iodide. Similarly, the reaction of 3‐methyl‐7‐phenylpyrazolo[1,5‐ a ]‐1,3,5‐dialkyl‐7‐phenylpyrazolo[1,5‐ a ]‐1,3,5‐triazine‐2,4‐diones. The starting materials, 3 and 17 , were prepared via the reaction of an appropriate 3‐aminopyrazole with ethoxycarbonyl isothiocyanate. Several 8‐bromo derivatives were prepared by direct bromination of the 1,3‐dialkylpyrazolo[1,5‐ a ]‐1,3,5‐triazine‐2,4‐diones.