The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

Erika Bálint, Ádám Tajti, Anna Ádám, István Csontos, Konstantin Karaghiosoff, Mátyás Czugler, Péter Ábrányi-Balogh and György Keglevich
Beilstein J. Org. Chem. 2017, 13, 76–86. https://doi.org/10.3762/bjoc.13.10

Supporting Information

Supporting Information File 1: Experimental, X-ray crystallographic data, and NMR spectra.
Format: PDF Size: 7.0 MB Download

Cite the Following Article

The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction
Erika Bálint, Ádám Tajti, Anna Ádám, István Csontos, Konstantin Karaghiosoff, Mátyás Czugler, Péter Ábrányi-Balogh and György Keglevich
Beilstein J. Org. Chem. 2017, 13, 76–86. https://doi.org/10.3762/bjoc.13.10

How to Cite

Bálint, E.; Tajti, Á.; Ádám, A.; Csontos, I.; Karaghiosoff, K.; Czugler, M.; Ábrányi-Balogh, P.; Keglevich, G. Beilstein J. Org. Chem. 2017, 13, 76–86. doi:10.3762/bjoc.13.10

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 146.4 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Veeranna, G.; Chittireddy, V. R. R.; Ravinder, V. Synthesis and characterization of Ru(II) complexes with polyfunctional amides and their application in catalytic oxidative coupling of amines. Results in Chemistry 2024, 9, 101618. doi:10.1016/j.rechem.2024.101618
  • Ravula, M.; Bandalla, S.; Dosarapu, V.; Kurra, M.; Mavurapu, S.; Vasam, C. S. Selective Synthesis of Imines via Oxidative Coupling of Primary Amines and Oxidation of Secondary Amines by Peroxides and other Competent Oxidants: A Short Review. Oriental Journal Of Chemistry 2024, 40, 611–629. doi:10.13005/ojc/400301
  • Ramani, A.; Bhavyesh, D.; Kanta Koppolu, M.; Chinna Ashalu, K.; Begari, E.; Naveen, T. An Efficient Synthesis of α‐Sulfonamide Phosphonates through Metal‐Free Three‐Component Reaction. Asian Journal of Organic Chemistry 2024, 13. doi:10.1002/ajoc.202400100
  • Soliya, S.; Kuperkar, K.; Ashalu, K. C.; Naveen, T. Catalyst‐Free Three‐Component Synthesis of α‐Amino Phosphonates. Asian Journal of Organic Chemistry 2024, 13. doi:10.1002/ajoc.202300572
  • Mandal, S.; Narvariya, R.; Sunar, S. L.; Paul, I.; Jain, A.; Panda, T. K. Synthesis of α-aminophosphorous derivatives using a deep eutectic solvent (DES) in a dual role. Green Chemistry 2023, 25, 8266–8272. doi:10.1039/d3gc02721j
  • Moiseev, D. V. Phospha-Mannich reactions of phosphinous acids R 2 P–OH and their derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements 2023, 198, 867–923. doi:10.1080/10426507.2023.2235054
  • Gábor, D.; Pollák, P.; Volk, B.; Dancsó, A.; Simig, G.; Milen, M. Catalyst‐ and Solvent‐Free Room Temperature Synthesis of α‐Aminophosphonates: Green Accomplishment of the Kabachnik–Fields Reaction. ChemistrySelect 2023, 8. doi:10.1002/slct.202301460
  • Kocsis, D.; Varga, P. R.; Keshwan, R.; Nader, M.; Lengyel, M.; Szabó, P.; Antal, I.; Kánai, K.; Keglevich, G.; Erdő, F. Transdermal Delivery of α-Aminophosphonates as Semisolid Formulations-An In Vitro-Ex Vivo Study. Pharmaceutics 2023, 15, 1464. doi:10.3390/pharmaceutics15051464
  • Tóth, S.; Keglevich, G.; Varga, P. R.; Dinnyési, E.; Szakács, G. Optimized Synthesis and Cytotoxic Activity of α-Aminophosphonates Against a Multidrug Resistant Uterine Sarcoma Cell Line. Letters in Drug Design & Discovery 2023, 20, 365–371. doi:10.2174/1570180819666220609104427
  • Arbuzova, S. N.; Verkhoturova, S. I.; Zinchenko, S. V.; Kolyvanov, N. A.; Chernysheva, N. A.; Bishimbaeva, G. K.; Trofimov, B. A. Catalyst‐ and Solvent‐Free Hydrophosphorylation of Aldimines with Secondary Phosphine Chalcogenides: Synthesis of Tertiary α‐Aminophosphine Oxides, Sulfides and Selenides. ChemistrySelect 2022, 7. doi:10.1002/slct.202202757
  • Kaboudin, B.; Faghih, S.; Alavi, S.; Naimi-Jamal, M. R.; Fattahi, A. An Efficient One-Pot Synthesis of 1-Aminophosphonates. Synthesis 2022, 55, 121–130. doi:10.1055/a-1941-1242
  • Lamberink, J.-W.; Boyle, P. D.; Gilroy, J. B.; Noël, J. J.; Blacquiere, J. M.; Ragogna, P. J. Reactivity of Primary Phosphines and Primary Phosphine Sulfides towards Imines. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 28, e202201565. doi:10.1002/chem.202201565
  • Cheng, X.-W.; Jin, W.-J.; Zhang, C.; Wu, Y.-X.; Guan, J.-P. Novel and durable flame-retardant modification based on the Schiff base and Pudovik reaction for wool fabric. Textile Research Journal 2021, 92, 3252–3260. doi:10.1177/00405175211063907
  • Chen, Z.-D.; Xu, W.-K.; Guo, J.-M.; Chen, L.; Wei, B.-G.; Si, C.-M.; Lin, G.-Q. A One-Pot Approach to 2-Substituted-2-(Dimethoxyphosphoryl)-Pyrrolidines from Substituted tert-Butyl 4-Oxobutylcarbamates and Trimethyl Phosphite. The Journal of organic chemistry 2021, 86, 11442–11455. doi:10.1021/acs.joc.1c00935
  • Amira, A.; Aouf, Z.; K'tir, H.; Chemam, Y.; Ghodbane, R.; Zerrouki, R.; Aouf, N.-E. Recent Advances in the Synthesis of α-Aminophosphonates: A Review. ChemistrySelect 2021, 6, 6137–6149. doi:10.1002/slct.202101360
  • Varga, P. R.; Keglevich, G. Synthesis of α-Aminophosphonates and Related Derivatives; the Last Decade of the Kabachnik-Fields Reaction. Molecules (Basel, Switzerland) 2021, 26, 2511. doi:10.3390/molecules26092511
  • Serafin-Lewańczuk, M.; Brzezińska-Rodak, M.; Lubiak-Kozłowska, K.; Majewska, P.; Klimek-Ochab, M.; Olszewski, T. K.; Żymańczyk-Duda, E. Phosphonates enantiomers receiving with fungal enzymatic systems. Microbial cell factories 2021, 20, 81. doi:10.1186/s12934-021-01573-8
  • Yuan, Q.; Liu, H.-W.; Cai, Z.-J.; Ji, S.-J. Direct 1,1-Bisphosphonation of Isocyanides: Atom- and Step-Economical Access to Bisphosphinoylaminomethanes. ACS omega 2021, 6, 8495–8501. doi:10.1021/acsomega.1c00160
  • Fiore, C.; Sović, I.; Lukin, S.; Halasz, I.; Martina, K.; Delogu, F.; Ricci, P. C.; Porcheddu, A.; Shemchuk, O.; Braga, D.; Pirat, J.-L.; Virieux, D.; Colacino, E. Kabachnik-Fields Reaction by Mechanochemistry: New Horizons from Old Methods. ACS Sustainable Chemistry & Engineering 2020, 8, 18889–18902. doi:10.1021/acssuschemeng.0c05744
  • Tajti, Á.; Tóth, N.; Rávai, B.; Csontos, I.; Szabó, P.; Bálint, E. Study on the microwave-assisted batch and continuous flow synthesis of N-alkyl-isoindolin-1-one-3-phosphonates by a special Kabachnik–Fields condensation. Molecules (Basel, Switzerland) 2020, 25, 3307. doi:10.3390/molecules25143307
Other Beilstein-Institut Open Science Activities