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

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

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 palladiu...

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Bibliographic Details
Published in:Research on chemical intermediates Vol. 45; no. 3; pp. 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: Journal Article
Language:English
Published: Dordrecht Springer Netherlands 15-03-2019
Springer Nature B.V
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
Palladium acetate
Bis
DNA gyrase
Antioxidant activity
aminophosphonates
Molecular docking
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Summary: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.
ISSN:0922-6168
1568-5675
DOI:10.1007/s11164-018-3685-5