Iminophosphoranes: Synthesis, evolution of synthesis by ³¹P-NMR, DFT calculations and antioxidant activity

References

• Ali, R. B.; Omrani, R.; Akacha, A. B.; Dziri, C.; El May, M. V. Véronique El May, M. Development and Validation of a Colorimetric Method for the Quantitative Analysis of Thioamide Derivatives. Spectrochim. Acta. A Mol. Biomol. Spectrosc. 2019, 220, 117154. DOI: 10.1016/j.saa.2019.117154.
   PubMed Web of Science ®Google Scholar
• Arar, W.; Khatyr, A.; Knorr, M.; Brieger, L.; Krupp, A.; Strohmann, C.; Efrit, M. L.; Ben Akacha, A. Synthesis, Crystal Structures and Hirshfeld Analyses of Phosphonothioamidates (EtO)2P(=O)C(=S)N(H)R (R = Cy, Bz) and Their Coordination on CuI and HgX2 (X = Br, I). Phosphorus Sulfur Silicon Relat. Elem. 2021, 196, 845–858. DOI: 10.1080/10426507.2021.1927032.
   Web of Science ®Google Scholar
• Mnallah, D. K.; Efrit, M. L.; Ben Akacha, A. Synthese De 1,3,2-Dioxaphosphorinanes Diastereoisomeres: Influence De la Conformation Des 1,3-Diols De Depart Sur Leurs Structures Et Conformations. Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 665–673. DOI: 10.1080/10426507.2017.1308931.
   Web of Science ®Google Scholar
• Staudinger, H.; Meyer, J. Über Neue Organische Phosphorverbindungen III. Phosphinmethylenderivate Und Phosphinimine. HCA 1919, 2, 635–646. DOI: 10.1002/hlca.19190020164.
   Web of Science ®Google Scholar
• Mitsunobu, O. The Use of Diethyl Azodicarboxylate and Triphenylphosphinein Synthesis and Transformation of Natural Products. Synthesis 1981, 1981, 1–28. DOI: 10.1055/s-1981-29317.
   Web of Science ®Google Scholar
• Molina, P.; Fresneda, P. M.; Hurtado, F. Iminophosphorane-Mediated Synthesis of Hetero-Arylmethylene-2-Aryl-2-Oxazolin-5-Ones. Synth. Commun 1987, 17, 485–490. DOI: 10.1080/00397918708063928.
   Web of Science ®Google Scholar
• Cortes, M. A.; Campa, R.; Valenzuela, M. L.; Diaz, C.; Carriedo, G. A.; Soto, A. P. Cylindrical Micelles by the Self-Assembly of Crystalline-b-Coil Polyphosphazene-b-P2VP Block Copolymers. Stabilization of Gold Nanoparticles. Molecules 2019, 24, 1772. DOI: 10.3390/molecules24091772.
   PubMed Web of Science ®Google Scholar
• Fang, J. K.; Xu, Z.; Sun, T.; Fang, Y.; Yin, Z.; Wang, S. Synthesis and Spectral Properties of Novel Iminophosphoranes. Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 1229–1234. DOI: 10.1080/10426507.2016.1165677.
   Web of Science ®Google Scholar
• Rodima, T.; Maements, V.; Koppel, I. Synthesis of N-Aryl-Substituted Iminophosphoranes and NMR Spectroscopic Investigation of Their Acid–Base Properties in Acetonitrile. J. Chem. Soc., Perkin Trans. 2000, 1, 2637–2644. DOI: 10.1039/b003575k.
   Google Scholar
• Kano, N.; Xing, J. H.; Kikuchi, A.; Kawa, S.; Kawashima, T. Synthesis of Four- and Five-Membered Heterocycles Derived from an Iminophosphorane. Phosphorus Sulfur Silicon Relat. Elem. 2002, 177, 1685–1687. DOI: 10.1080/10426500290092875.
   Web of Science ®Google Scholar
• Nunez, N. G.; Farley, A. J. M.; Dixon, D. J. Bifunctional Iminophosphorane Organocatalysts for Enantioselective Synthesis: Application to the Ketimine Nitro-Mannich Reaction. J. Am. Chem. Soc. 2013, 135, 16348–−16351. DOI: 10.1021/ja409121s.
   PubMed Web of Science ®Google Scholar
• Crisan, M. E.; Vlase, G.; Vlase, T.; Croitor, L.; Ilia, G.; Bourosh, P. N.; Kravtsov, V. C.; Petric, M. F. Thermogravimetric and Kinetic Study of New Bis(Iminophosphorane) Ethane Solvates. J. Therm. Anal. Calorim. 2020, 141, 1009–1016. DOI: 10.1007/s10973-020-09628-5.
   Web of Science ®Google Scholar
• Weinert, M.; Döring, M. N-Phosphorylated Iminophosphoranes Based on 9,10-Dihydro-9-Oxa-10-Phosphaphenanthrene-10-Oxide and Their Flame-Retardant Behavior in Epoxy Resins. J. Appl. Polym. Sci. 2021, 138, 49902. DOI: 10.10002/app.49902.
   Web of Science ®Google Scholar
• Bednarek, C.; Wehl, I.; Jung, N.; Schepers, U.; Bräse, S. The Staudinger Ligation. Chem. Rev 2020, 10, 4301–4354. DOI: 10.1021/acs.chemrev.9b00665.
   Google Scholar
• Ramazani, A.; Souldozi, A. Iminophosphorane-Mediated One-Pot Synthesis of 1,3,4-Oxadiazole Derivatives. Arkivoc 2008, 2008, 235–242. DOI: 10.3998/ark.5550190.0009.g22.
   Google Scholar
• Ramazani, A.; Ahmadi, Y.; Tarasi, R. Efficient One-Pot Synthesis of Disubstituted 1,3,4-Oxadiazole Derivatives from the Reaction of (N-Isocyanimino)Triphenylphosphorane, Acetaldehyde, a Secondary Amine, and an Electron-Poor (E)-Cinnamic Acid. Heteroatom Chem 2011, 22, 79–84. DOI: 10.1002/hc.20660.
   Web of Science ®Google Scholar
• Ramazani, A.; Souldozi, A. The Reaction of (N-Isocyanimino)Triphenylphosphorane with Anthranilic Acid Derivatives: One-Pot Synthesis of 2-Substituted 1,3,4-Oxadiazoles via Intramolecular Aza-Wittig Reaction. Phosphorus Sulfur Silicon Relat. Elem 2009, 184, 2344–2350. DOI: 10.1080/10426500802466684.
   Web of Science ®Google Scholar
• Souldozi, A.; Ślepokura, K.; Lis, T.; Ramazani, A. Synthesis and Single Crystal X-Ray Structure of 2-(1,3,4-Oxadiazol- 2-yl)Aniline. Z Naturforsch B 2007, 62, 835–840. DOI: 10.1515/znb-2007-0613.
   Google Scholar
• Ramazani, A.; Nasrabadi, F. Z.; Ahmadi, Y. One-Pot, Four-Component Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (Isocyanoimino)Triphenylphosphorane, a Primary Amine, an Aromatic Carboxylic Acid, and Chloroacetone. HCA 2011, 94, 1024–1029. DOI: 10.1002/hlca.201000356.
   Web of Science ®Google Scholar
• Nasrabadi, F. Z.; Ramazani, A.; Ahmadi, Y. Synthesis of Sterically Congested 1,3,4-Oxadiazole Derivatives from Aromatic Carboxylic Acids, N,N-Dicyclohexylcarbodiimide and (N-Isocyanimino)Triphenylphosphorane. Mol Divers 2011, 15, 791–798. DOI: 10.1007/s11030-011-9310-9.
   PubMed Web of Science ®Google Scholar
• Ramazani, A.; Nasrabadi, F. Z.; Karimi, Z.; Rouhan, M. Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines. Bull. Korean Chem. Soc 2011, 32, 2700–2704. DOI: 10.5012/bkcs.2011.32.8.2700.
   Web of Science ®Google Scholar
• Boubekeur, L.; Ricard, L.; Mézailles, N.; Le Floch, P. Synthesis of New Mixed Phosphine ∼ Iminophosphorane Bidentate Ligands and Their Coordination to Group 10 Metal Centers. Organometallics 2005, 24, 1065–1074. DOI: 10.1021/om0490684.
   Web of Science ®Google Scholar
• Cheisson, T.; Auffrant, A. Versatile Coordination Chemistry of a Bis(Methyliminophosphoranyl)Pyridine Ligand on Copper Centres. Dalton Trans. 2014, 43, 13399–13409. DOI: 10.1039/c4dt01794c.
   PubMed Web of Science ®Google Scholar
• 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. DOI: 10.1002/adsc.201300091.
   Web of Science ®Google Scholar
• Cheisson, T.; Ricard, L.; Heinemann, F. W.; Meyer, K.; Auffrant, A.; Nocton, G. Synthesis and Reactivity of Low-Valent f-Element Iodide Complexes with Neutral Iminophosphorane Ligands. Inorg. Chem. 2018, 57, 9230–−9240. DOI: 10.1021/acs.inorgchem.8b01259.
   PubMed Web of Science ®Google Scholar
• Qin, J.; Zhou, Z.; Cui, T.; Hemming, M.; Meggers, E. Enantioselective Intramolecular C-H Amination of Aliphatic Azides by Dual Ruthenium and Phosphine Catalysis. Chem. Sci. 2019, 10, 3202–3207. DOI: 10.1039/C9SC00054B.
   PubMed Web of Science ®Google Scholar
• Golec, J. C.; Carter, E. M.; Ward, J. W.; Whittingham, W. G.; Simon, L.; Paton, R. S.; Dixon, D. J. BIMP-Catalyzed 1,3-Prototropic Shift for the Highly Enantioselective Synthesis of Conjugated Cyclohexenones. Angew. Chem. 2020, 132, 17570–17577. DOI: 10.1002/anie.202006202.
   Google Scholar
• Formica, M.; Rozsar, D.; Su, G.; Farley, A. J. M.; Dixon, D. J. Bifunctional Iminophosphorane Superbase Catalysis: Applications in Organic Synthesis. Acc. Chem. Res. 2020, 53, 2235–2247. DOI: 10.1021/acs.accounts.0c00369.
   PubMed Web of Science ®Google Scholar
• Frik, M.; Jiménez, J.; Vasilevski, V.; Carreira, M.; De Almeida, A.; Gascón, E.; Benoit, F.; Sanaú, M.; Casini, A.; Contel, M. Luminescent Iminophosphorane Gold, Palladium and Platinum Complexes as Potential Anticancer Agents. Inorg. Chem. Front. 2014, 1, 231–241. DOI: 10.1039/c4qi00003j.
   PubMed Web of Science ®Google Scholar
• Lease, N.; Vasilevski, V.; Carreira, M.; De Almeida, A.; Sanaú, M.; Hirva, P.; Casini, A.; Contel, M. Potential Anticancer Heterometallic Fe-Au and Fe-Pd Agents: Initial Mechanistic Insights. J. Med. Chem. 2013, 56, 5806–5818. DOI: 10.1021/jm4007615.
   PubMed Web of Science ®Google Scholar
• Frik, M.; Gallardo, J. F.; Gonzalo, O.; Sanjuan, V. M.; Alvarez, M. G.; Del Valle, A. S.; Hu, C.; Alvarez, I. G.; Bermejo, M.; Marzo, I.; Conte, M. Cyclometalated Iminophosphorane Gold(III) and Platinum(II) Complexes. A Highly Permeable Cationic Platinum(II) Compound with Promising Anticancer Properties. J. Med. Chem. 2015, 58, 5825–5841. DOI: 10.1021/acs.jmedchem.5b00427.
   PubMed Web of Science ®Google Scholar
• Carreira, M.; Sanjuan, R. C.; Sanau, M.; Marzo, I.; Contel, M. Organometallic Palladium Complexes with a Water-Soluble Iminophosphorane Ligand as Potential Anticancer Agents. Organometallics 2012, 31, 5772–5781. DOI: 10.1021/om3006239.
   PubMed Web of Science ®Google Scholar
• Frik, M.; Martínez, A.; Elie, B. T.; Gonzalo, O.; De Mingo, D. R.; Sanau, M.; Delgado, R. S.; Sadhukha, T.; Prabha, S.; Ramos, J.; et al. In Vitro and in Vivo Evaluation of Water-Soluble Iminophosphorane Ruthenium (II) Compounds. A Potential Chemotherapeutic Agent for Triple Negative Breast Cancer. J. Med. Chem. 2014, 23, 9995–10012. DOI: 10.1021/jm5012337.
   Google Scholar
• Staudinger, H.; Hauser, E. Uber Neue, Organkche Phosphorverbindungen IV. Phosphinimine. HCA 1921, 4, 861–886. DOI: 10.1002/hlca.19210040192.
   Google Scholar
• Leffler, J. E.; Temple, R. D. The Staudinger Reaction between Triarylphosphines and Azides. A Study of the Mechanism. J. Am. Chem. Soc 1967, 20, 5235–5246. DOI: 10.1021/ja00996a027.
   Google Scholar
• Lin, F. L.; Hoyt, H. M.; Halbeek, H. V.; Bergman, R. G.; Bertozzi, C. R. Mechanistic Investigation of the Staudinger Ligation. J. Am. Chem. Soc. 2005, 127, 2686–2695. DOI: 10.1021/ja044461m.
   PubMed Web of Science ®Google Scholar
• Tian, W. Q.; Wang, Y. A. Mechanisms of Staudinger Reactions within Density Functional Theory. J. Org. Chem. 2004, 69, 4299–4308. DOI: 10.1021/jo049702n.
   PubMed Web of Science ®Google Scholar
• Rao, A. J.; Rao, V. K.; Rao, P. V.; Krishna, B. S.; Raju, C. N.; Ghosh, S. K. Synthesis and Biological Activity of DiazaphospholoIminophosphorane Derivatives of Zidovudine (Azt) through Staudinger Reaction. Int. J. Pharm. Bio. Sci. 2010, V1.
   Google Scholar
• Reddy, M. V. N.; Reddy, G. C. S.; Kumar, K. S.; Reddy, C. S.; Raju, C. N. Synthesis, Antioxidant and Antimicrobial Activity of Novel Benzene-1,4-Diamine-Bis-Dioxaphosphepine-6λ5 Iminophosphoranes. J. Heterocycl. Chem 2010, 47, 538–542. DOI: 10.1002/jhet.358.
   Web of Science ®Google Scholar
• Alvarez, S. G.; Alvarez, M. T. A Practical Procedure for the Synthesis of Alkyl Azides at Ambient Temperature in Dimethyl Sulfoxide in High Purity and Yield. Synthesis 1997, 1997, 413–414. DOI: 10.1055/s-1997-1206.
   Google Scholar
• Molina, P.; López-Leonardo, C.; Llamas-Botía, J.; Foces-Foces, C.; Fernández-Castaño, C. Unexpected Staudinger Reaction of α-Azidoacetonitriles α-Phenyl Substituted with Triphenylphosphine. Preparation, X-Ray Crystal and Molecular Structures of a Phosphazine, an Aminophosphonium Carbanion Salt and a Phosphazide, with (Z)-Configuration. Tetrahedron 1996, 52, 9629–9642. DOI: 10.1016/0040-4020(96)00499-1.
   Web of Science ®Google Scholar
• Yamaguchi, T.; Takamura, H.; Matoba, T.; Terao, J. HPLC Method for Evaluation of the Free Radical-Scavenging Activity of Foods by Using 1,1-Diphenyl-2-Picrylhydrazyl. Biosci. Biotechnol. Biochem. 1998, 62, 1201–1204. DOI: 10.1271/bbb.62.1201.
   PubMed Web of Science ®Google Scholar
• Frisch, M. J. Gaussian 09. Revision D.01; Gaussian Inc: Wallingford, CT, 2013.
   Google Scholar
• Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys 1993, 98, 5648–5652. DOI: 10.1063/1.464913.
   Web of Science ®Google Scholar
• Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B. Condens. Matter. 1988, 37, 785–789. DOI: 10.1103/physrevb.37.785.
   PubMed Web of Science ®Google Scholar
• Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements. Theor. Chem. Account. 2008, 120, 215–−241. DOI: 10.1007/s00214-007-0310x.
   Web of Science ®Google Scholar
• Padmaja, A.; Rajasekhar, C.; Muralikrishna, A.; Padmavath, V. Synthesis and Antioxidant Activity of Oxazolyl/Thiazolylsulfonylmethyl Pyrazoles and Isoxazoles. Eur. J. Med. Chem. 2011, 46, 5034–5038. DOI: 10.1016/j.ejmech.2011.08.010.
   PubMed Web of Science ®Google Scholar