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
Synthesis 2014; 46(15): 2079-2084
DOI: 10.1055/s-0033-1341064
DOI: 10.1055/s-0033-1341064
paper
A One-Pot, Three-Step Synthesis of α-Aminophosphonic Acids
Further Information
Publication History
Received: 05 February 2014
Accepted after revision: 06 March 2014
Publication Date:
11 April 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201415/lookinside/thumbnails/10.1055-s-0033-1341064-1.jpg)
Abstract
A total of 20 α-aminophosphonic acids are synthesized in 73–89% yields via a one-pot, three-step procedure involving chlorotrimethylsilane-promoted condensation of carbonyl compounds and primary amines yielding azomethine intermediates, subsequent reaction with tris(trimethylsilyl) phosphite to give the corresponding trimethylsilylphosphonic esters and finally, mild cleavage with methanol–water. The wide scope and simple set-up and work-up procedures of the reported method allow the synthesis of a diverse set of α-aminophosphonic acids possessing two different functional groups.
Key words
α-aminophosphonic acids - aldehydes - amines - chlorotrimethylsilane - tris(trimethylsilyl) phosphite - one-pot synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity. Kukhar VP, Hudson HR. John Wiley & Sons; Chichester: 2000
- 1b Kudzin ZH, Kudzin MH, Drabowicz J, Stevens CV. Curr. Org. Chem. 2011; 15: 2015
- 1c Turcheniuk KV, Kukhar VP, Röschenthaler G.-V, Aceña JL, Soloshonok VA, Sorochinsky AE. RSC Adv. 2013; 3: 6693
- 1d Ali TE. ARKIVOC 2014; (i): 21
- 2a Mucha A, Kafarski P, Berlicki L. J. Med. Chem. 2011; 54: 5955
- 2b Romanenko VD, Kukhar VP. Chem. Rev. 2006; 106: 3868
- 2c Naydenova ED, Todorov PT, Troev KD. Amino Acids 2010; 38: 23
- 3 Hiratake J, Oda J. Biosci. Biotechnol. Biochem. 1997; 61: 211
- 4a Allen JG, Atherton FR, Hall MJ, Hassall CH, Holmes SW, Lambert RW, Nisbet LJ, Ringrose PS. Nature 1978; 272: 56
- 4b Pratt RF. Science 1989; 246: 917
- 5 Chen M.-H, Chen Z, Song B.-A, Bhadury PS, Yang S, Cai X.-J, Hu D.-Y, Xue W, Zeng S. J. Agric. Food Chem. 2009; 57: 1383
- 6 Maier L, Diel PJ. Phosphorus, Sulfur Silicon Relat. Elem. 1991; 57: 57
- 7 Duke SO, Powles SB. Pest Manag. Sci. 2008; 64: 319
- 8a Moedritzer K, Irani RR. J. Org. Chem. 1966; 31: 1603
- 8b Lazar I, Sherry AD. Synthesis 1995; 453
- 8c Bazakas K, Lukes I. J. Chem. Soc., Dalton Trans. 1995; 1133
- 8d Convey PV, Davey RJ, Griffin JL, Whiting A. Chem. Commun. 1998; 1467
- 9a Kabachnik MI, Medved TYa, Dyatlova NM, Arkhipova OG, Rudomino MV. Russ. Chem. Rev. (Engl. Transl.) 1968; 38: 503
- 9b Gallardo-Macias R, Nakayama K. Synthesis 2010; 57
- 10a Alfonsov VA. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 2637
- 10b Issleib K, Ralszuweit A, Richter H.-J, Tonk W. Z. Chem. 1983; 23: 434
- 11 Firouzabadi H, Iranpoor N, Sobhani S. Synthesis 2004; 2692
- 12 Saidi MR, Azizi N. Synlett 2002; 1347
- 13a Kudzin ZH, Kotynski A. Synthesis 1980; 1028
- 13b Huber R, Knierzinger A, Obrecht J.-P, Vasella A. Helv. Chim. Acta 1985; 68: 1730
- 13c Liavielle G, Hautefaye P, Schaeffer C, Boutin JA, Cudennec CA, Pierre A. J. Med. Chem. 1991; 34: 1998
- 14a Bird J, Mello RC. D, Harper GP, Hunter DJ, Karran EH. J. Med. Chem. 1994; 37: 158
- 14b Jacobsen EN, Joly GD. J. Am. Chem. Soc. 2004; 126: 4102
- 15a Maier L, Diel PJ. Phosphorus, Sulfur Silicon Relat. Elem. 1991; 57: 57
- 15b Cherenok S, Kalchenko V, Solovyov A, Tsymbal I, Failla S, Consiglio GA, Finocchiaro P. Heteroat. Chem. 2001; 12: 58
- 16 Ntai I, Bachmann BO. Bioorg. Med. Chem. Lett. 2008; 18: 3068
- 17a Bouchemal N, Lecouvey M, Mallard I, Migianu E. Tetrahedron Lett. 2004; 45: 4511
- 17b Guliaiko IV, Kolodiazhnyi OI. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 677
- 18a Migianu-Griffoni E, Mbemba C, Burgada R, Lecouvey M, Lecercle D, Taran F. Tetrahedron 2009; 65: 1517
- 18b Zhang Y, Leon A, Song Y, Studer D, Haase C, Koscielski LA, Oldfield E. J. Med. Chem. 2006; 49: 5804
- 19 Nifant’ev EE, Popkova TN, Kukhareva TS, Bekker AR. J. Gen. Chem. USSR (Engl. Transl.) 1988; 58: 1550
- 20a Boduszek B, Lipinski M, Kowalska MW. Phosphorus, Sulfur Silicon Relat. Elem. 1998; 143: 179
- 20b Mlynarz P, Rydzewska A, Sliwinska S, Szymczyk M. Phosphorus, Sulfur Silicon Relat. Elem. 2009; 184: 1496
- 21 Ryabukhin SV, Panov DM, Plaskon AS, Chuprina A, Tolmachev AA, Shivanyuk AN. Mol. Diversity 2012; 16: 625