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Studies on enaminonitriles: A new synthesis of 1,3-substituted pyrazole-4-carbonitrile

✍ Scribed by Said Ahmed Soliman Ghozlan; Ismail Abdelshafy Abdelhamid; Mohamed Hilmy Elnagdi; Hatem Moustafa Gaber

Book ID
102344896
Publisher
Journal of Heterocyclic Chemistry
Year
2005
Tongue
English
Weight
88 KB
Volume
42
Category
Article
ISSN
0022-152X

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✦ Synopsis

3-Diethylaminoacrylonitrile (1) reacts with hydrazonyl halides (2a-d) to yield 1,3-disubstituted pyrazole-4-carbonitriles 5a-d. The acetyl 1-p-chlorophenylpyrazole-4-carbonitrile (5a) condensed with hydrazine hydrate to yield the bishydrazone 10 and with dimethylformamide dimethylacetal to yield 1-aryl-3-(3dimethylamino)acryloyl pyrazole-4-carbonitrile (11). This enamine reacts with hydrazine hydrate to yield the pyrazolylpyrazole ( 12) and with naphthoquinone to yield the 3-naphthofuranoyl pyrazole 13. The pyrazolyl pyridine derivative 14 was obtained upon treatment of 11 with acetylacetone in the presence of ammonium acetate. Compound 11 was coupled with p-chlorobenzene diazonium chloride to yield the hydrazone 16 that was coupled further with p-chlorobenzenediazonium chloride to yield the formazane 18.

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## Abstract magnified image 3‐Amino‐3‐phenyl‐2‐phenylazoacrylonitrile **6** is obtained in good yield __via__ reaction of **5** with phenyl magnesium bromide. The compound **6** is readily converted into **4a**. The so formed alkanenitrile reacted with phenylmagnesium bromide to yield **8**. Compo