Nano Structured Bi2O3 Catalyzed Synthesis of 3-Phenyl-[1,2,4]Triazolo[3,4-a]Phthalazines and Their Cross-coupling Reaction Under Aqueous Conditions

Chacko, Priya; Shivashankar, Kalegowda

doi:10.1080/10406638.2019.1585375

Cited by 6 publications

(1 citation statement)

References 22 publications

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“…Various synthetic routes have been established for the construction of 1,2,4‐triazolophthalazine motifs. Among them, the use of nano‐Bi 2 O 3 catalyst and (diacetoxyiodo)benzene reagent were considered important routes for the synthesis of 1,2,4‐triazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Cu(II)‐promoted cyclization of hydrazonophthalazine to triazolophthalazine; Synthesis and structure diversity of six novel Cu(II)‐triazolophthalazine complexes

Soliman

Albering

El‐Faham

2019

Applied Organom Chemis

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A novel route for the synthesis of Cu(II)-triazolophthalazine complexes using the Cu(II)-promoted cyclization dehydrogenation reactions of hydrazonophthalazines under reflux was presented. Two hydrazonophthalazines were cyclized to the corresponding triazolophthalazine ligands, 3-pyridin-2-yl-3,10b-dihydro- [1,2,4]triazolo[3,4-a]phthalazine (TPP) and 3-(3,10b-dihydro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-benzoic acid (TP3COOH), followed by in situ complexation with Cu(II) yielding six novel Cu(II)-triazolophthalazine complexes depending on the reaction conditions. The molecular and supramolecular structures of the Cu(II)-triazolophthalazine complexes were discussed. The metal sites have rectangular pyramidal geometry in the [Cu(TPP)Cl 2 ] 2 ; 1 and [Cu(TP3COOEt)Cl 2 (H 2 O)] 2 ; 4 dinuclear complexes, distorted square planar in [Cu(TP3COOMe) 2 Cl 2 ]; 3, [Cu(TP3COOH) 2 Cl 2 ]; 5 and [Cu(TP3COOH) 2 Cl 2 ]·H 2 O; 6 and a distorted octahedral in [Cu(TPP)(H 2 O) 2 (NO 3 ) 2 ]; 2. Hirshfeld analysis showed that the O…H, C…H, Cl…H (except TP3COOH and 2), N…H and π-π stacking interactions are the most important intermolecular contacts. The π-π stacking interactions are the maximum for TP3COOH and complex 6 with net C…C/C…N contacts of 19.4% and 15.4%, respectively. The orbital-orbital interaction energies of the Cu-N/Cu-Cl bonds correlated inversely with the corresponding Cu-N/Cu-Cl distances, respectively. The charge transfer processes between Cu(II) and ligand groups were also discussed. The charge densities of the Cu(II) centers are reduced to 0.663-0.995 e due to the interactions with the ligand groups coordinating it.

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Section: Introductionmentioning

confidence: 99%