Ajaya Kumar Behera

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

Nitrogen‐, and/or Sulfur-Containing Heterocyclic Rings Poulomi Majumdar,†,‡ Anita Pati,†,§ Manabendra Patra, Rajani Kanta Behera,† and Ajaya Kumar Behera*,† †Organic Synthesis Laboratory, School of Chemistry, Sambalpur University, Jyoti Vihar, Burla 768019, Orissa, India ‡State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, 116024, P.R. China School of Applied Sciences (Chemistry), KIIT University, Bhubaneswar 751024, India National Institute of Science & Technology, Palur Hill, Berhampur 761068, Orissa, India

Chemistry of Dimedone for Synthesis of Oxygen-, Nitrogen-, and Sulfur- Containing Heterocycles from 2-(3-Hydroxy-5,5-dimethylcyclohex-2-enylidene)malononitrile

Abstract A series of new oxygen-, nitrogen- and sulfur- containing spiro heterocycles was synthesized by reactions of 2-(3-hydroxy-5,5-dimethylcyclohex-2-enylidene)malononitrile with some active methylene and bidentate compounds. GRAPHICAL ABSTRACT

Synthesis of 3-Substituted Pyrazole Derivatives by Mixed Anhydride Method and Study of Their Antibacterial Activities

Abstract A convenient synthesis of 3-substituted pyrazole derivatives by a mixed anhydride method using i-butylchloroformate and N-methylmorpholine at −20 °C in tetrahydrofuran and study of in vitro antibacterial activities of the prepared compounds against Staphylococcus epidermidis, Bacillus subtilis, Pseudomonas aeruginosa, and Proteus valguris by agar-diffusion method were carried out. The results suggested that the products 4a, 4b, and 4c exhibited moderate to feeble inhibition against all test bacteria at greater concentration but 4d was best against Staphylococcus epidermidis (22 mm) and worst against Pseudomonas aeruginosa (16 mm) at the greatest concentration (2.5 mg/ml), and the activities decreased with decrease in concentration. [Supplementary materials are available for this article. Go to the publishers online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] GRAPHICAL ABSTRACT

Design, Synthesis, and Cytotoxicity of Novel 3‐Arylidenones Derived from Alicyclic Ketones

Forty‐four novel chalcone‐inspired analogs having a 3‐aryl‐2‐propenoyl moiety derived from alicyclic ketones were designed, synthesized, and investigated for cytotoxicity against murine B16 and L1210 cancer cell lines. The analogs belong to four structurally divergent series, three of which (series g, h, and i) contain differently substituted cyclopentanone units and the fourth (series j) contains a 3,3‐dimethyl‐4‐piperidinone moiety. Of these, the analogs in series j showed potential cytotoxic activity against murine B16 (melanoma) and L1210 (lymphoma) cells. The most active compounds 5j, 11j, 15j, and 12h produced IC50 values from 4.4 to 15 μm against both cell lines. A single‐crystal X‐ray structure analysis and molecular modeling studies confirmed that these chalcones have an E‐geometry about the alkene bond and possess a slightly ‘twisted’ conformation similar to that of combretastatin A‐4. At a concentration of 30 μm, compounds 5j, 11j, and 15j did not cause microtubule depolymerization in cells, suggesting that they have a different mechanism of action.

5-Benzyl-idene-3-phenyl-2-phenyl-imino-1,3-thia-zolidin-4-one.

The title compound, C22H16N2OS, is a chalcone analog with a thiazolidinone core that was synthesized as a potential cytotoxic and anticancer agent. The structure is commensurately modulated by unit-cell doubling along the direction of the a axis of the cell. The two crystallographically independent molecules are differerentiated by the dihedral angle between the mean planes of the benzylidene phenyl group against the thiazolidin-4-one moiety, which is 5.01 (7)° in one molecule, and 17.41 (6)° in the other. The two molecules are otherwise close to being indistinguishable and are related by crystallographic pseudo-translation. The two molecules are not planar but are slightly bent with the benzylidene and phenylimino substituents being bent upwards with respect to the center planes of the two molecules. The degree of bending of the two halves of the thiazolidin-4-one moieties (defined as the planes that intersect at the S atom) are 11.08 (7) and 15.88 (7)°. Packing of the molecules is facilitated by C—H⋯π interactions and slipped π–π stacking between one of the phenyl rings and a neighboring ethylene π system [distance between the centroid of the ethylene group and the closest phenyl C atom = 3.267 (2) Å, Cg(phenyl)⋯Cg(ethylene) = 3.926 Å].

Studies on the synthesis of spiroheterocycles and their derivatives using dimedone as synthetic precursor

Abstract Diarylidene ketones 1a–c, formed by the condensation of acetone with diverse appropriate aryl aldehydes undergo Micheal reaction with dimedone to afford the desired spiro compounds 2a–c. The spirodiarylidene derivatives 3a–l on cyclisation with hydrazine, phenyl hydrazine, hydroxyl amine, urea, thiourea and guanidine carbonate furnish the respective insitu oxidized pyrazole 4a–l, phenylpyrazole 5a–l, isoxazole 6a–l, pyrimidine 7a–l, aminopyrimidine 8a–l. The antibacterial activities of the synthesized compounds have been investigated against the gram negative Escherichia coli and gram positive bacteria Staphylococcus aureus. Graphical Abstract Diarylidene ketone undergo Micheal rection with dimedone to afford the spiro compounds followed by cyclisation with some bidentate ligands to furnish the respective insitu oxidized pyrazole, phenylpyrazole, isoxazole, pyrimidine, aminopyrimidine derivatives and the synthesized compounds were screened for their antibacterial activities.