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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.

A novel series of cyclic 2-oxindole derivatives incorporating 2-amino-tetrahydroquinolin-5-one were prepared. The structures of the prepared compounds were elucidated using different spectral tools. The regio-orientation of the reaction products was elucidated through NOE difference experiments and through using substituents on the ortho position to affect further cyclization. Antitumor and antimicrobial evaluations were performed on the prepared compounds. Most of these compounds exhibited high to moderate antimicrobial activity. With respect to the antitumor activity, the compounds showed more potent cytotoxic effect only toward the human breast cancer cell line MCF-7. Also, we found that derivatives containing an ester group (8c, 11b, 14b, and 15b) are more active than those containing a cyanide group (8a, 11a, 14a, and 15a). Moreover, compounds 15b and 8b are the most active derivatives in this group. These two compounds showed apoptotic inhibition of the proliferation of human breast adenocarcinoma MCF-7 cells through DNA fragmentation, induction of the tumor suppressor protein p53, induction of caspase-9, and finally the inhibition of angiogenesis by decreasing vascular endothelial growth factor expression and secretion.

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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Novel bis‐chromeno[2,3‐b]pyridine derivatives were synthesized with good yields by a clean and efficient methodologies involving one‐pot three‐component synthesis of bis‐aldehydes, malononitrile dimer, and dimedone in the presence of piperidine as a catalyst in EtOH. Depending on the length and position of the spacer in the bis‐aldehyde derivatives 1, the reactions proceeded to give either the bis(2,4‐diamino‐tetrahydro‐5H‐chromeno[2,3‐b]pyridine‐3‐carbonitriles) 4 or bis(4‐amino‐2,6‐dioxo‐hexahydro‐2H‐chromeno[2,3‐b]pyridine‐3‐carbonitriles) 5. All of the new compounds have been characterized by spectral data.