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Ultrasound assisted synthesis of Diethyl (2-(1-(morpholinomethyl)-2-oxoindolin-3-ylidene)hydrazinyl) (substituted phenyl/heteryl) methylphosphonate Derivatives.
1 , 2 , 2 , * 3
1  Department of Pharmaceutical Chemistry, Durgamata Institute of Pharmacy, Parbhani, Maharashtra, India
2  Departamento de Química Orgánica, Facultad de Ciencias, Universidad of Santiago De Compostela, Alfonso X el Sabio, Lugo 27002, Spain
3  Wilson college, Girgaon Chawpatty,Mumbai 400007 , Maharashtra, India


The work reports Ultrasound assisted diethyl (2-(1-(morpholinomethyl)-2-oxoindolin-3-ylidene)hydrazinyl) (substituted phenyl/heteryl) methylphosphonate 9(a-j) derivatives. The derivatives are synthesized using green protocol. In the first step 3-hydrazonoindolin-2-one is synthesized using ultrasound. In the second step diethyl (substituted phenyl/heteryl)(2-(2-oxoindolin-3-ylidene)hydrazinyl) methylphosphonate 6(a-j) derivatives using cerric ammonium nitrate as catalyst. In the third step diethyl (2-(1-(morpholinomethyl)-2-oxoindolin-3-ylidene)hydrazinyl) (substituted phenyl/heteryl) methylphosphonate 9(a-j) derivatives are synthesized using ultrasound. Isatin, chemically known as H-indole-2,3-dione, and its derivatives possess a broad range of biological and pharmacological properties. Isatin is widely used as starting material for the synthesis of a broad range of heterocyclic compounds and as substrates for drug synthesis. The α-amino phosphonate derivatives constitute an important class of organophosphorus compounds on account of their versatile biological activity. morpholine moiety has been found to be of an eminent pharmacophore in medicinal chemistry. A number of molecules possessing morpholine moiety are clinically approved drugs. The importance of this ring is well understood by medicinal chemists, since they play a major role in molecular properties such as an electronic distribution, three dimensionality, scaffold flexibility/rigidity, lipophilicity or polarity and metabolic stability. Considering the importance of the three pharmacophores, promoted us to club these pharmacophores together in a single molecule using green synthetic protocol. The structures of the ultrasound synthesized compounds were confirmed by spectral analysis like IR, 1H NMR, 13C NMR, 31P NMR and MS.

Keywords: Ultrasound assisted; Cerric Ammonium Nitrate; Isatin; α-amino phosphonate.