Palladium acetate-catalysed one-pot green synthesis of bis α-aminophosphonates

• Published in: Research on chemical intermediates 2019-03, Vol.45 (3), p.1401-1420
• Main Authors: Sadik, Shaik Mahammad, Santhisudha, Sarva, Mohan, Gundluru, Reddy, Nadiveedhi Maheshwara, Lakshmi, Poola Sree, Rajasekhar, Allagadda, Rao, Chippada Appa, Reddy, Cirandur Suresh
• Format: Article
• Language: English
• Subjects: Aldehydes; Antioxidants; Aromatic compounds; Ascorbic acid; Catalysis; Chemical analysis; Chemical synthesis; Chemistry; Chemistry and Materials Science; Deoxyribonucleic acid; DNA; Hydrogen peroxide; Infrared analysis; Inorganic Chemistry; Inorganic salts; Mass spectra; Molecular docking; NMR; Nuclear magnetic resonance; Palladium; Physical Chemistry; Scavenging
• ISSN: 0922-6168; 1568-5675
• DOI: 10.1007/s11164-018-3685-5

A simple and effective green method has been developed for the synthesis of a series of novel bis α -aminophosphonate derivatives ( 4a–j) by the reaction of 1,4-diaminonaphthalene, various aryl/heteroaryl aldehydes and dialkyl phosphites under neat and microwave irradiation conditions using palladium acetate as catalyst. The products are characterized by elemental analysis, IR, 1 H, 13 C, 31 P-NMR and mass spectra and their antioxidant activities are evaluated by DPPH, NO and H 2 O 2 methods and molecular docking studies. The compounds 4d and 4h exhibited the highest radical scavenging activity in the DPPH method, while compounds 4a , 4e and 4f showed good NO scavenging activity. The compound 4g showed remarkably higher H 2 O 2 scavenging activity than even the standard ascorbic acid, and compound 4h has stronger inhibiting activity on DNA gyrase enzyme.