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An efficient synthesis of enaminones 1a-c is reported. Compounds 1a-c reacted with diethyl-3-amino-2cyanopenten-1,5-dicarboxylate (3) to yield the benzonitriles 6. On the other hand, the reaction of 1a-c with 3-amino-2-cyano-2-pentene dinitrile (7) afforded a mixture of benzonitriles 10 and pyridines 9. The reaction of 1a-c with 3-aminocrotononitrile 11 has afforded the 4-substituted-3-cyano-2-methylpyridines 15a-c. The reaction of ethylene diamine with 1a-c afforded 5-substituted-2,3-dihydro-1H-[1,4]diazepines 18a-c. On the other hand, 1a-c reacted with o-phenylenediamine to yield the 4-(2-aminopheynlamino)-substituted enaminones 21. Compounds 21 could be converted into the benzotriazolylenones 22 on treatment with sodium nitrite in acetic acid solution.

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.