Premium
Studies with functionally substituted N ‐alkylazoles: The reactivity of 1‐(3,5‐dimethylpyrazol‐1‐yl)‐acetone towards electrophilic reagents
Author(s) -
Mohamed Mona Hassan,
Elnagdi Mohamed Hilmy,
AbdelKhalik Mervat Mohammed
Publication year - 2001
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.5570380324
Subject(s) - chemistry , phenylhydrazine , dimethylformamide , acetone , methylene , reagent , yield (engineering) , organic chemistry , electrophile , hydrochloric acid , reactivity (psychology) , condensation , nitrous acid , medicinal chemistry , catalysis , solvent , medicine , materials science , alternative medicine , physics , pathology , metallurgy , thermodynamics
The reaction of 1‐(3,5‐dimethylpyrazol‐1‐yl)acetone 4 with aromatic diazonium salts afforded the corresponding arylhydrazones 5a,b that were converted into pyridazines 6a,b and 8 via condensation with active methylene nitriles and dimethylformamide dimethylacetal, respectively. Condensation of 4 with phenylhydrazine afforded the phenylhydrazone 10 , which could be converted into the indolylpyrazole 11 on treatment with ethanolic hydrochloric acid. Compound 4 also reacted with nitrous acid, benzyl‐idenemalononitrile to yield a variety of substituted new pyrazoles.