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Ultrasound Assisted Synthesis of Diethyl (2-(1-(morpholinomethyl)-2-Oxoindolin-3-ylidene)hydrazinyl) (Substituted Phenyl/heteryl) MethylphosphonateDerivatives

1
Department of Pharmaceutical Chemistry, Durgamata Institute of Pharmacy, Dharmapuri, Parbhani 431401, Maharashtra, India
2
Departamento de QuímicaOrgánica, Facultad de Ciencias, Universidad of Santiago De Compostela, Alfonso X el Sabio, Lugo 27002, Spain
3
Wilson College, Girgaon Chawpatty, Mumbai 400007, Maharashtra, India
*
Author to whom correspondence should be addressed.
Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22.
Proceedings 2019, 9(1), 3; https://doi.org/10.3390/ecsoc-22-05790
Published: 14 November 2018
PDF [367 KB, uploaded 14 March 2019]

Abstract

This work reports ultrasound assisted synthesis diethyl (2-(1-(morpholinomethyl)-2-oxoindolin-3-ylidene)hydrazinyl) (substituted phenyl/heteryl) methylphosphonate 9(a–j) derivatives. The derivatives are synthesized using a 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 are synthesized 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 a 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 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, this promoted us to club these pharmacophores together in a single molecule using a 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 ultrasound assisted; cerric ammonium nitrate; isatin; α-amino phosphonate
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Tiwari, S.V.; Seijas, J.A.; Vazquez-Tato, M.P.; Nikalje, A.P.G. Ultrasound Assisted Synthesis of Diethyl (2-(1-(morpholinomethyl)-2-Oxoindolin-3-ylidene)hydrazinyl) (Substituted Phenyl/heteryl) MethylphosphonateDerivatives. Proceedings 2019, 9, 3.

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