American Journal of Innovative Research & Applied Sciences
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| ARTICLES | Am. J. innov. res. appl. sci. Volume 5, Issue 4, Pages 246-249 (October 2017)
American Journal of innovative
Research & Applied Sciences
ISSN 2429-5396 (Online)
OCLC Number: 920041286
| OCTOBER | VOLUME 5 | N° 4 | 2017 |
*Correspondant author and authors Copyright © 2017: | El Houssine Mabrouk 1 | and | Boukallaba Khalid 1 |
1. University Sidi Mohamed Ben Abdellah | Faculty of Sciences Dhar El Mehraz | department of Chemistry | Fez | Morocco |
This article is made freely available as part of this journal's Open Access: ID | Abounada-ManuscriptRef.7-ajira240817 |
Background: we reported in this paper another part of our investigations concerning the preparation of diethyl (2-benzoylamino-2-(phenylsulfanyl) methyl) phosphonate and diethyl (2-benzoylamino-2-(4-chloro- phenylsulfanyl) methyl) phosphonate 2-3, with the aim to have access to new active biomolecules with a good yield through S-alkylation reaction. Objectives: α-Amino esters possess a broad range of applications ranging from agrochemistry to medicine. We developed a simple, efficient, and environmentally benign method for the Synthesis of new racemic phosphonic α-amino esters by S-alkylation of diethyl (2-azido-2-benzoylaminomethyl) phosphonate with aromatic thiols (thiophenol and 4-chloro thiophenol). The structures of the newly synthesized compounds were supported by 1H NMR, 13C-NMR and mass spectral data. This method has advantages of mild condition, no environmental pollution, and simple work-up procedures. Most importantly, compounds of α-phosphonic aminoesters are obtained in acceptable to moderate yields by this methodology. Methods: The S-alkylation of diethyl (2-azido-2-benzoylaminomethyl) phosphonate with aromatic thiols (thiophenol and 4-chloro thiophenol) are performed in different solvents (acetone and acetonitrile) for 48 h at room temperature in the presence of various bases (Et3N and DIEPA). Results: The products 2-3 synthesized with a satisfactory yields were characterized by nuclear magnetic resonance and mass spectrometry. Conclusions: we have developed an environmentally friendly, mild condition protocol and convenient procedure for the preparation of new phosphonic α-aminoesters derivatives starting from the appropriate azide derivative 1. The nucleophilic substitution of azide with different thiols (thiophenol and 4-chloro thiophenol) occurred under very mild conditions and led after a reaction time of about 48 hours to the desired products with a satisfactory yields.
Keywords: α-amino ester, S-alkylation, thiophenol, diethyl (2-azido-2-benzoylaminomethyl) phosphonate.
SYNTHESIS OF NEW α-AMINO PHOSPHONATES
| El Houssine Mabrouk 1 | and | Boukallaba Khalid 1 |. Am. J. innov. res. appl. sci. 2017; 5(4):246-249.
| PDF FULL TEXT | |Received | 24 August 2017| |Accepted | 15 September 2017| |Published 24 September 2017 |