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Original Articles

New class of diethyl substituted phosphoramidimidates and phosphonimidates: synthesis, spectral characterization and antimicrobial activity

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Pages 853-857 | Received 13 Mar 2018, Accepted 15 Aug 2018, Published online: 10 Oct 2018

References

  • Greenwood, N.; Earnshaw, A. Chemistry of the Elements. Oxford: Pergamon, 1984.
  • Rueping, M.; Nachtsheim, B. J.; Ieawsuwan, W.; Atodiresei, I. Modulating the Acidity: Highly Acidic Bronsted Acids in Asymmetric Catalysis. Angew. Chem. Int. Ed. 2011, 50, 6706–6720. DOI: 10.1002/anie.201100169.
  • Szulc, I.; Kołodziuk, R.; Kryczka, B.; Zawisza, A. New Phosphine-Imine Ligands Derived from d-Gluco- and d-Galactose in Pd-Catalysed Asymmetric Allylic Alkylation. Tetrahedron Lett. 2015, 56, 4740–4743. DOI: 10.1016/j.tetlet.2015.06.031.
  • (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. Catalytic Asymmetric Hydrogenation. Chem. Commun. 1972, 0, 10–11. DOI: 10.1039/C39720000010. (b) Lega, M.; Margalef, J.; Ruffo, F.; Pamies, O.; Dieguez, M. Application of pyranoside phosphite-pyridine ligands to enantioselective metal-catalyzed allylic substitutions and conjugate 1,4-additions. Tetrahedron: Asymmetry. 2013, 24, 995–1000. DOI: 10.1016/j.tetasy.1013.06.011.
  • Boiteau, J. G.; Imbos, R.; Minnard, A. J.; Feringa, B. L. Rhodium-Catalyzed Asymmetric Conjugate Additions of Boronic Acids Using Monodentate Phosphoramidite Ligands. Org. Lett. 2003, 5, 681–684. DOI: 10.1021/ol027465.
  • Mucha, A.; Kunert, A.; Grembecka, J.; Pawełczak, M.; Kafarski, P. A Phosphonamidate Containing Aromatic N-Terminal Amino Group as Inhibitor of Leucine Aminopeptidase-Design, Synthesis and Stability. Eur. J. Med. Chem. 2006, 41, 768–772. DOI: 10.1016/j.ejmech.2006.03.023.
  • Madhurima, H.; Kyalo, S. K.; Takanori, S. Enantioselective Synthesis of Planar-Chiral 1,11-Dioxa[11]Paracyclophane-Derived Phosphoramidities and Their Use as Chiral Ligands. Tetrahedron: Asymmetry. 2016, 27, 1081–1087. DOI: 10.1016/j.tetasy.2016.08.015.
  • Fang, J.-K.; Xu, Z.; Sun, T.; Fang, Y.; Yin, Z.; Wang, S. Synthesis and Spectral Properties of Novel Iminophosphoranes. Phosphorus Sulfur Silicon. 2016, 191, 1229–1234. DOI: 10.1080/10426507.2016.1165677.
  • Baumgartner, T.; Reau, R. Organophosphorus π-Conjugated Materials. Chem. Rev. 2006, 106, 4681–4727. DOI: 10.1021/cr040179m.
  • Blackstone, V.; Lough, A. J.; Murray, M.; Manners, I. Probing the Mechanism of the PCl5−Initiated Living Cationic Polymerization of the Phosphoranimine Cl3P=NSiMe3 Using Model Compound Chemistry. J. Am. Chem. Soc. 2009, 131, 3658–3667. DOI: 10.1021/ja808517d.
  • Foster, R. S.; Jakobi, H.; Harrity, J. P. A General and Regioselective Synthesis of 5-Trifluoromethyl-Pyrazoles. Org. Lett. 2012, 14, 4858–4861. DOI: 10.1021/ol3021918.
  • Monnereau, L.; Sémeril, D.; Matt, D. Calixarene-Derived Mono-Iminophosphoranes: Highly Efficient Ligands for Palladium- and Nickel-Catalysed Cross-Coupling. Adv. Synth. Catal. 2013, 355, 1351–1360. DOI: 10.1002/adsc.201300091.
  • Kanazawa, C.; Terada, M. Dichotomous Control of E/Z‐Geometry in Intramolecular Cyclization of o‐Alkynylbenzamide Derivatives Catalyzed by Organic Superbase P4‐tBu in the Presence/Absence of Water. Chem. Asian J. 2009, 4, 1668–1672. DOI: 10.1002/asia.200900342.
  • Goldys, A. M.; Nunez, M. G.; Dixon, D. J. Creation through Immobilization: A New Family of High Performance Heterogeneous Bifunctional Iminophosphorane (BIMP) Superbase Organocatalysts. Org. Lett. 2014, 16, 6294–6297. DOI: 10.1021/ol5029942.
  • Molina, P.; Murcia, F.; Fresneda, P. M. A Straight Forward and Practical Formal Synthesis of Lavendamycin Ethyl Ester. Tetrahedron Lett 1994, 35, 1453–1456. DOI: 10.1016/S0040-4039(00)76244-7.
  • Molina, P.; Almendros, P.; Fresneda, P. M. Iminophosphorane-Mediated Imidazole Ring Formation: A New and General Entry to Aplysinopsin-Type Akaloids of Marine Origin. Tetrahedron. 1994, 50, 2241–2254. DOI: 10.1016/S0040-4039(00)78515-7.
  • Molina, P.; Almendros, P.; Fresneda, P. M. An Iminophosphorane-Mediated Efficient Synthesis of the Alkaloid Leucettamine B of Marine Origin. Tetrahedron Lett. 1994, 35, 2235–2236. DOI: 10.1016/S0040-4039(00)76806-7.
  • Molina, P.; Fresneda, P. M.; García-Zafra, S.; Almendros, P. Iminophosphorane-Mediated Syntheses of the Fascaplysin Alkaloid of Marine Origin and Nitramarine. Tetrahedron Lett. 1994, 35, 8851–8854. DOI: 10.1016/S0040-4039(00)78515-7.
  • Staudinger, H.; Meyer, J. Uberneue Organische Phosphorverbindungen III. Phosphinmethylenderivate and Phosphinimine. Hca. 1919, 2, 635–646. DOI: 10.1002/hlca.19190020164.
  • Varalakshmi, M.; Naga Raju, C. Nucleoside Substituted Perhydro-1λ5-[1,3,2]Diazaphospholo[1,5-a]Pyridine-1-Thione Analogues: Synthesis and Evaluation of Antiviral and Antimicrobial Activities. Orgcommun. 2018, 11, 35–45. DOI: 10.25135/.acg.oc.35.17.12.055.
  • Varalakshmi, M.; Srinivasulu, D.; Venkata Kotakadi, S. Nano-BF3.SiO2 Catalyst-Promoted Michaelis-Arbuzov Reaction: Solvent-Free Synthesis and Antimicrobial Evaluation. Phosphorus, Sulfur, Silicon Relat. Elem. 2015, 190, 1518–1524. DOI: 10.1080/10426507.2014.996643.

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