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The present study illustrates conventional and microwave reactions of 5‐amino‐1,3‐diaryl‐pyrazole‐4‐carbonitrile derivative with phenacyl bromide under different conditions, hydrazine hydrate, hydroxylamine hydrochloride, tetrahydrofuran, phthalic anhydride, and cyanoacetic acid. The product of the latter reaction condensed with hydrazine and cyclohexanone to give the pyrazolotriazepine acetonitrile and cyclohexylidene derivatives. The new cyclohexylidene is used as key intermediate to synthesize some new spiro compounds. The behavior of the starting compound with benzaldehyde, ethylenediamine, phenylenediamine, sodium azide, 1‐amino‐2‐hydroxynaphthalene‐7‐sulphonic acid, diethylmalonate, terephthalaldehyde, acetyl chloride, and acetic anhydride were also investigated. The new compounds structures were established from spectroscopic data. Some of the new pyrazole derivatives showed antibacterial and anticancer activities.

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in Wiley Online Library (wileyonlinelibrary.com).Enaminonitrile derivatives 1a and 1b were used as a versatile material for the synthesis of different heterocyclic compounds such as pyrazoloacetamide, pyrazolopyrimidinone, pyrazolobenzamide, pyrazolopyrimidines, pyrazolothiazinethione, pyrazolopyrimidinedithione, pyrazolocyanoacetamide, pyrazolopyrazole, tetrazolopyrazole, pyrazolotetrazolopyrimidine, and pyrazolotetrazolodiazepine derivatives, through the reaction with different electrophiles and nucleophiles. The newly synthesized compounds were tested against Gram-positive and Gram-negative bacteria, fungi, and two human tumor cell lines. Scheme 3. Synthetic routes for the preparation of compounds 10-12. Scheme 4. Synthetic routes for the preparation of compounds 13-17.

Under both conventional and microwave methods, 2‐amino‐4H‐pyran‐3‐carbonitrile derivative 1 was synthesized and reacted with different reagents. Thus, 2‐amino‐4H‐pyran‐3‐carbonitrile derivative was treated with chloroacetyl chloride, phenyl isocyanate, cyanoacetic acid, benzoyl chloride, triethyl orthoformate, acetic anhydride/H2SO4, arylidene malononitrile, urea, and/or p‐aminosulphaguanidine producing chloroacetamide, 3‐phenylurea, cyanoacetamide, N‐benzoylpyran, ethylformimidate, pyranopyrimidin‐4‐one, pyranopyridine, pyranopyrimidin‐2‐one, and pyranopyrimidin‐2‐imine derivatives, respectively. Meanwhile, compound 1 was reacted with ethyl bromoacetate, phenacyl bromide, phthalic anhydride, different aromatic amines, and/or acetic acid/H2SO4 to produce 5‐aminopyrano[2,3‐b]pyrrole‐6‐carboxylate, dihydropyrano[2,3‐b]pyrrole‐6‐yl‐(phenyl)methanone, 1,3‐dioxoisoindolinyl pyran, 1,4‐dihydropyridine, and 2‐hydroxy‐1,4‐dihydropyridine derivatives, respectively. On the other hand, when compound 1 was allowed to react with maleic anhydride and/or hydrazine hydrate, pyran‐4‐oxobut‐2‐enoic acid and 3‐aminopyranopyrazole derivatives were obtained, respectively. Reaction of pyran‐4‐oxobut‐2‐enoic acid with malononitrile under different conditions gave 2‐(furan‐2‐yl)‐4H‐pyran and 2‐(4H‐pyran‐2‐yl)‐1H‐pyrrole derivatives, while condensation of 3‐aminopyranopyrazole with benzaldehyde gave 1,4‐dihydropyrano[2,3‐c]pyrazol‐3‐yl‐1‐phenylmethanimine derivative. The newly synthesized compounds were characterized by the spectroscopic tools IR, 1H‐NMR, 13C‐NMR, MS, and elemental analysis. Some of these compounds have been screened in vitro for antimicrobial activity against different strains of bacteria and fungi and also were tested against two cancer cell lines: mammary gland breast cancer (MCF‐7) and colon cancer (HCT‐118).