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Studies with 3-functionally substituted 2-arylhydrazononitriles: A new route to 3-substituted-2-arylhydrazononitriles, 4-amino-pyrazole-5-carbonitriles, azadienes and cinnolines

✍ Scribed by Ramadan M. Abdel-Motaleb; Abdel-Moneim A. Makhloof; Hamada M. Ibrahim; Mohamed H. Elnagdi

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
138 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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. Compound 8 could be also obtained from reaction of 9 with phenylmagnesium bromide. The arylhydrazononitriles 8 and 4a reacted with chloroacetonitrile to yield the 4‐aminopyrazoles 12a,b. Compound 12a reacted with acetic anhydride to yield the 15a and with benzoyl chloride to yield the pyrazole 16 which was converted into 15b. Refluxing 10 in acetic acid gave a mixture of the azadiene 21 and the cinnoline 22 is obtained. The azadiene 21 is converted into 22 either thermally or photochemically.

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Studies with 3-Functionally Substituted
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Studies with 2-arylhydrazononitriles: A
Studies with 2-arylhydrazononitriles: A novel simple, efficient route to 5-acyl-2-substituted-1,2,3-triazol-4-amines
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