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We report an unprecedented multicomponent reaction of acetoacetanilide with malononitrile leading to a structurally novel bicyclic product (9) in a high yield. The structure has been confirmed by X-ray crystallography and comparative Hirshfeld surface analysis of 5-cyano-2-hydroxy-2-methyl-N-phenyl-4-(yridine-4-yl)-6-(thiophen-2-yl)-3,4-dihydro-2H-pyran-3-carboxamide 2, 5-cyano-2-hydroxy-2-methyl-6-oxo-N-phenyl-4-(thiophen-2-yl)piperidine-3-carboxamide 4 and 2-(8-amino-7,8a-dicyano-1-imino-4a-methyl-3-oxo-2-phenyl-1,3,4,4a,5,8a-hexahydroisoquinolin-6(2H)-ylidene)-N-phenylacetamide 9.

In the molecular structure of the title compound, C16H13Cl2N5, the 1,4-dihydropyridine ring of the 1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine ring system adopts a screw-boat conformation, while the 1,3-diazinane ring is puckered. In the crystal, intermolecular N—H...N and C—H...N hydrogen bonds form molecular sheets parallel to the (110) and (\overline{1}10) planes, crossing each other. Adjacent molecules are further linked by C—H...π interactions, which form zigzag chains propagating parallel to [100]. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from N...H/H...N (28.4%), H...H (24.5%), C...H/H...C (21.4%) and Cl...H/H...Cl (16.1%) contacts.

SHORT COMMUNICATIONSWhile continuing our studies in the fields of synthesis and transformations of 1,2-chlorohydrins [1] obtained by reaction of arenes with 3-chloro-1,2-epoxypropane in the presence of aluminum chloride, we performed oxidation of 3-chloro-1-(2,4,6-trimethylphenyl)propan-2-ol (I) with chromium(VI) oxide and isolated 3-chloro-1-(2,4,6-trimethylphenyl)propan-2one (II). α-Chloro ketone II was brought into reaction with various primary amines in aqueous potassium hydroxide at room temperature. The reaction time was 20-45 min. Regardless of the amine nature, in all cases the products were the corresponding N-substituted 3-(2,4,6-trimethylphenyl)propionamides III-IX which were isolated in 50-97% yield as colorless crystalline substances and were recrystallized from ethanol.

In the title compound, C25H20O2, the central cyclohexenone ring adopts an envelope conformation. The mean plane of the cyclohexenone ring makes dihedral angles of 87.66 (11) and 23.76 (12)°, respectively, with the two attached phenyl rings, while it is inclined by 69.55 (11)° to the phenyl ring of the benzoyl group. In the crystal, the molecules are linked by C—H...O and C—H...π interactions, forming a three-dimensional network.

In this study, it was shown that pyrimidine and imidazopyridine derivatives were obtained from the multicomponent reaction of isatylidene malononitriles with malononitrile and diamines at room temperature. Also, the interaction of 2-(5-bromo-2oxoindoline-3-ylidene)with malononitrile and benzoyl acetone (or ethyl-4-chlorine-acetoacetate) was carried out and the formation of the corresponding pyran derivatives was observed.The structure of the synthesized compounds was confirmed by 1 H, 13 CNMR spectroscopy and X-ray analysis. The acetylcholinesterase (AChE) inhibitor compounds recorded as important therapeutic drugs for the therapy of Alzheimer's disease. Also, novel complexes effectively inhibited AChE enzyme, with Ki values in the range of 4.56 to 8.21 μM. For this enzyme, it was obtained with IC50 values in the range of 4.04 to 9.85 μM. For α-glycosidase enzyme the most effective Ki values were for 4 a and 10 compounds with Ki values of 31.48 and 32.63 μM, respectively. The molecular docking study was employedto investigate of chemical activities and interaction of synthesized compounds with low Ki in the presence of AChE, butyrylcholinesterase, and α-Glycosidase. The results revealed that some of the compounds, like compound 9 have a good binding affinity to AChE with a docking score of À 6.243 (kcal/mol). This compound can affect the enzyme activity by attachment to essential residues of the catalytic domain of the enzyme. The ADME/T analysis was also performed and revealed that compounds have the potential to be utilized as medicine.

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