DABCO Catalyzed Synthesis of β‐Hydroxy Ketones Derived from α‐Methyl Ketones and Ninhydrin under Microwave Irradiations

Verma, Pratibha; Mishra, Ankush; Chauhan, Swati; Singh, Sundaram; Srivastava, Vandana

doi:10.1002/slct.201900720

Cited by 8 publications

(5 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The precursors 2‐substituted‐2‐hydroxy‐indane‐1,3‐diones [22] and 1,4‐benzoxazinones [23] were synthesized according to the literature methods. We have chosen 1 and 7 as model substrates for the optimization of reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

Construction of Polyheterocyclic Compounds by Lewis Acid Mediated Intramolecular [3+2] Cycloaddition Reaction

et al. 2023

View full text Add to dashboard Cite

An efficient domino approach has been developed for the synthesis of polyheterocyclic derivatives constituting pyrrole moiety. Lewis acid catalyzed reaction of 2‐substituted‐2‐hydroxy‐indane‐1,3‐diones and 1,4‐benzoxazinone derivatives resulted in the formation of polyheterocyclic compounds under metal‐free and mild conditions in good to excellent yield. The reaction is highly regioselective for C−C and C−N bond construction proceeded via intramolecular [3+2] cycloaddition reaction. The protocol is highly efficient, obviates column chromatography and the products are obtained by simple filtration followed by washing with solvent.

show abstract

Section: Resultsmentioning

confidence: 99%

Construction of Polyheterocyclic Compounds by Lewis Acid Mediated Intramolecular [3+2] Cycloaddition Reaction

et al. 2023

View full text Add to dashboard Cite

show abstract

“…We commenced our work by synthesizing precursors such as 2-substituted-2-hydroxy-indane-1,3-diones, 31 benzylidene succinimides, 32 and ( E )-4-arylidene-5-methyl-2-phenyl-2,4-dihydro-3 H -pyrazol-3-ones 33 using literature procedures.…”

Section: Resultsmentioning

confidence: 99%

Spirocyclization and Michael addition of 3-benzylidene succinimides: route to spirocyclopentapyrrolidine-tetraones and benzylidene N-arylpyrrolidine-diones

Dahiya,

Yadav,

Peddinti

2023

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

“…Alloxan and ninhydrin are privileged compounds because of their inclusive range of applications in biological and organic synthesis fields [ 1 – 5 ]. Alloxan is considered an example of a pyrimidine derivative while ninhydrin possesses an indanone core moiety that is found in many natural products.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Physicochemical Characterization, Biological Assessment, and Molecular Docking Study of Some Metal Complexes of Alloxan and Ninhydrin as Alterdentate Ligands

Masoud

Yacout

Abd-El-Khalek

et al. 2023

J Inorg Organomet Polym

View full text Add to dashboard Cite

A series of transition metal complexes of alloxan monohydrate (H2L1) and ninhydrin (H2L2) have been prepared where metal ions are Fe(III), Co(II), Ni(II), Cu(II), Zr(IV), and Mo(VI). Different microanalytical techniques, spectroscopic methods, and magnetic studies were applied to assign the mode of bonding and elucidate the structure of complexes. All solid complexes are of 1:1 (M:L) stoichiometry and octahedral geometry except nickel (II) complexes exist in a tetrahedral geometry. FTIR spectral interpretation reveals that HL1 coordinates to the central metal ion in a bidentate ON pattern, whereas HL2 behaves as an alterdentate ligand through hydroxyl oxygen and carbonyl oxygen either C(1) = O or C(3) = O. The thermal behavior of some complexes was followed up to 700 °C by different techniques (TGA, DTA, and DSC) where decomposition stages progress in complicated mechanisms and are ended by the formation of metal oxide residue. Besides, biological screening involving antioxidant, antibacterial, and antifungal for ligands and some of their complexes was done. Moreover, four examined metal complexes displayed anticancer activity against hepatocellular carcinoma cells (HepG-2) but to different degrees. According to the IC50 values, Cu-ninhydrin complex, [Cu(HL2)(H2O)4].Cl has a better potency impact in comparison with cisplatin which was used as a reference control. This is in harmony with the molecular docking simulation outcomes that predicted a good binding propensity of the Cu-ninhydrin complex with hepatocellular carcinoma protein (2jrs). Therefore, the Cu-ninhydrin complex should be deemed as a potential chemotherapeutic agent for hepatocellular cancer. Graphical Abstract

show abstract

DABCO Catalyzed Synthesis of β‐Hydroxy Ketones Derived from α‐Methyl Ketones and Ninhydrin under Microwave Irradiations

Cited by 8 publications

References 35 publications

Construction of Polyheterocyclic Compounds by Lewis Acid Mediated Intramolecular [3+2] Cycloaddition Reaction

Construction of Polyheterocyclic Compounds by Lewis Acid Mediated Intramolecular [3+2] Cycloaddition Reaction

Spirocyclization and Michael addition of 3-benzylidene succinimides: route to spirocyclopentapyrrolidine-tetraones and benzylidene N-arylpyrrolidine-diones

Synthesis, Physicochemical Characterization, Biological Assessment, and Molecular Docking Study of Some Metal Complexes of Alloxan and Ninhydrin as Alterdentate Ligands

Contact Info

Product

Resources

About