Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2020; 52(10): 1531-1540
DOI: 10.1055/s-0039-1691599
DOI: 10.1055/s-0039-1691599
paper
Catalyst- and Solvent-Free Synthesis of α-Amino Polyfluoroalkylphosphonates from Bis(fluoroalkyl) Phosphonates and Aldimines
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.
Key words
bis(fluoroalkyl) phosphonates - aldimines - catalyst-free - solvent-free - α-amino polyfluoroalkylphosphonatesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691599.
- 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