Synthesis 2020; 52(10): 1531-1540
DOI: 10.1055/s-0039-1691599
paper
© Georg Thieme Verlag Stuttgart · New York

Catalyst- and Solvent-Free Synthesis of α-Amino Polyfluoroalkylphosphonates from Bis(fluoroalkyl) Phosphonates and Aldimines

Svetlana N. Arbuzova
,
Nina K. Gusarova
,
Tatyana I. Kazantseva
,
Svetlana I. Verkhoturova
,
Sergey V. Zinchenko
,
Nikita A. Kolyvanov
,
Boris A. Trofimov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
› Author Affiliations
This work has been approved by plans for research projects at the IPC RAS State Registration No. AAAA-A16-116112510005-7.
Further Information

Publication History

Received: 12 December 2019

Accepted after revision: 19 January 2020

Publication Date:
13 February 2020 (online)


Abstract

The catalyst- and solvent-free reaction between bis(fluoroalkyl) phosphonates and aldimines occurs under mild conditions (20–22 °C, 0.25–4 h) to afford a new family of α-amino polyfluoroalkylphosphonates in up to quantitative yields.

Supporting Information

 
  • References

    • 1a Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity. Kukhar VP, Hudson HR. Wiley; Chichester: 2000
    • 1b Kafarski P, Lejczak B. Curr. Med. Chem.: Anti-Cancer Agents 2001; 1: 301
    • 1c Romanenko VD, Kukhar VP. Chem. Rev. 2006; 106: 3868
    • 1d Lejczak B, Kafarski P. Top. Heterocycl. Chem. 2009; 20: 31
    • 1e Orsini F, Sello G, Sisti M. Curr. Med. Chem. 2010; 17: 264
    • 1f Mucha A, Kafarski P, Berlicki Ł. J. Med. Chem. 2011; 54: 5955
    • 1g Turcheniuk KV, Kukhar VP, Röschenthaler G.-V, Aceňa JL, Soloshonok VA, Sorochinsky AE. RSC Adv. 2013; 3: 6693
    • 2a Hiyama T. Organofluorine Compounds . Springer; Berlin: 2000
    • 2b Ismail FM. D. J. Fluorine Chem. 2002; 118: 27
    • 2c Burger’s Medicinal Chemistry and Drug Discovery, 6th ed., Vol. 1. Abraham DJ. Wiley; New York: 2003
    • 2d Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications. Wiley-VCH; Weinheim: 2013
    • 2e Chambers RD. Fluorine in Organic Chemistry, 2nd ed.. Blackwell; Oxford: 2004
    • 2f Kirk KL. J. Fluorine Chem. 2006; 127: 1013
    • 2g Hagmann WK. J. Med. Chem. 2008; 51: 4359
    • 2h Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
    • 2i Fluorinated Heterocycles, ACS Symposium Series, Vol. 1003. Gakh A, Kirk KL. American Chemical Society; Washington: 2009
    • 2j Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications. Petrov VA. Wiley; Hoboken: 2009
    • 2k Fluorine in Heterocyclic Chemistry . Nenajdenko V. Springer; Heidelberg: 2014
  • 3 Prchalová E, Štěpánek O, Smrček S, Kotora M. Future Med. Chem. 2014; 6: 1201
    • 4a Kamiya N, Kubota A, Iwase Y, Sekiya K, Ubasawa M, Yuasa S. Antimicrob. Agents Chemother. 2002; 46: 2872
    • 4b Lu P, Jiang SH, Liu JX, Yang YS, Ji RY. Chin. Chem. Lett. 2009; 20: 507
    • 4c Krutikov VI, Erkin AV. Russ. J. Gen. Chem. 2009; 79: 1645
    • 4d Fu XZ, Ou Y, Xin J, Yang YS. Chin. Chem. Lett. 2011; 22: 1387
    • 4e Wu D, Niu J.-Q, Ding Y.-H, Wu X.-Y, Zhong B.-H, Feng X.-W. Med. Chem. Res. 2012; 21: 1179
    • 4f Mandadapu SR, Gunnam MR, Kankanamalage AC. G, Uy RA. Z, Alliston KR, Lushington GH, Kim Y, Chang K.-O, Groutas WC. Bioorg. Med. Chem. Lett. 2013; 23: 5941
    • 4g Baszczyňski O, Janeba Z. Med. Res. Rev. 2013; 33: 1304
    • 4h Liao S, Fan S.-Y, Liu Q, Li C.-K, Chen J, Li J.-L, Zhang Z.-W, Zhang Z.-Q, Zhong B.-H, Xie J.-W. Arch. Pharm. Res. 2014; 37: 1416
    • 5a Soon DK. W, Lowe SL, Teng CH, Yeo KP, McGill J, Wise SD. J. Hepatol. 2004; 41: 852
    • 5b Chan C, Abu-Raddad E, Golor G, Watanabe H, Sasaki A, Yeo KP, Soon D, Sinha VP, Flanagan SD, He MM, Wise SD. Antimicrob. Agents Chemother. 2005; 49: 1813
    • 5c Zhang P, Guo J, Meng F, Sun L, Zhong B, Zhao Y. J. Pharm. Biomed. Anal. 2012; 61: 70
    • 6a Krutikova VV, Krutikov VI, Erkin AV. Russ. J. Gen. Chem. 2010; 80: 434
    • 6b Skoreńsky M, Oleksyszyn J, Sieńczyk M. Tetrahedron Lett. 2013; 54: 1566
    • 6c Kim I.-H, Park Y.-K, Nishiwaki H, Hammock BD, Nishi K. Bioorg. Med. Chem. 2015; 23: 7199
  • 7 Odinets IL, Artyushin OI, Goryunov EI, Lyssenko KA, Rybalkina EYu, Kosilkin IV, Timofeeva TV, Antipin MYu. Heteroat. Chem. 2005; 16: 497
    • 8a Arbuzova SN, Gusarova NK, Kazantseva TI, Verkhoturova SI, Albanov AI, Afonin AV, Trofimov BA. Tetrahedron Lett. 2016; 57: 3515
    • 8b Arbuzova SN, Gusarova NK, Kazantseva TI, Verkhoturova SI, Albanov AI, Trofimov BA. J. Fluorine Chem. 2018; 210: 137
    • 9a Pudovik AN. Dokl. Akad. Nauk SSSR 1952; 83: 865 ; Chem. Abstr. 1953, 47, 4300
    • 9b Sobanov AA, Zolotukhin AV, Galkin VI, Cherkasov VA, Pudovik AN. Russ. J. Gen. Chem. 2002; 72: 1067
    • 10a Ordóñez M, Sayago FJ, Cativiela C. Tetrahedron 2012; 68: 6369
    • 10b Ordóñez M, Viveros-Ceballos JL, Cativiela C, Sayago FJ. Tetrahedron 2015; 71: 1745
    • 10c Sobkowski M, Kraszewski A, Stawinski J. Top. Curr. Chem. 2015; 361: 179
    • 10d Abdel-Rahman RM, Ali TE, Abdel-Kariem SM. ARKIVOC 2016; (i): 183
    • 10e Ganoub NA, Sabry E, Abdou WM. Synth. Commun. 2017; 47: 1631
  • 11 Olszewski TK. Synthesis 2014; 46: 403
    • 12a Moglie Y, González-Soria MJ, Martín-García I, Radivoy G, Alonso F. Green Chem. 2016; 18: 4896
    • 12b Gusarova NK, Chernysheva NA, Trofimov BA. Synthesis 2017; 49: 4783
    • 13a Clarke PA, Santos S, Martin WH. C. Green Chem. 2007; 9: 438
    • 13b Vereshchagin AN, Elinson MN, Anisina YuE, Ryzhkov FV, Goloveshkin AS, Bushmarinov IS, Zlotin SG, Egorov MP. Mendeleev Commun. 2015; 25: 424
    • 14a Abell JP, Yamamoto H. J. Am. Chem. Soc. 2008; 130: 10521
    • 14b Liu Q, Yu S, Hu L, Hussain MI, Zhang X. Tetrahedron 2018; 74: 7209
    • 15a Mironov VF, Konovalova IV. Russ. J. Gen. Chem. 1993; 63: 1548
    • 15b Timperley CM, Arbon RE, Saunders SA, Waters MJ. J. Fluorine Chem. 2002; 113: 65
  • 16 Texier-Boullet F. Synthesis 1985; 679