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Pyrimidine derivatives and related compounds. A novel synthesis of pyrimidines, pyrazolo[4,3‐ d ]pyrimidines and isoxazolo[4,3‐ d ] pyrimidine
Author(s) -
Elnagdi Mohamed Hilmy,
Fahmy Shereif Mahmoud,
Hafez Ebtisam Abdel Aziz,
Elmoghayar Mohamed Riffaat Hamza,
Amer Samir Abdel Rahman
Publication year - 1979
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.5570160606
Subject(s) - chemistry , hydrazine (antidepressant) , yield (engineering) , hydrate , pyrimidine , medicinal chemistry , derivative (finance) , 2 aminopyridine , organic chemistry , stereochemistry , materials science , chromatography , economics , financial economics , metallurgy
Benzoylacetonitrile (II) reacted with trichloroacetonitrile (III) to yield the β‐amino‐β‐trichloromethylacrylonitrile IV. Compound IV reacted with hydrazine hydrate to yield 5‐amino‐4‐cyano‐3‐phenylpyrazole (V) and with 2‐aminopyridine to yield the aminopyridine derivative VIII ( cf ., Chart I). Compound IV reacted with III to yield 2,4‐bis(trichloromethyl)‐5‐cyano‐6‐phenylpyrimidine (I) which could be converted into a variety of pyrazolo[4,3‐ d ]pyrimidine derivatives by treatment with hydrazine hydrate under a variety of different experimental conditions ( cf ., Chart II).