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 2015; 47(13): 1869-1876
DOI: 10.1055/s-0034-1380523
DOI: 10.1055/s-0034-1380523
paper
A Simple and Green Procedure for the One-Pot Synthesis of α-Aminophosphonates with Quaternary Ammonium Salts as Efficient and Recyclable Reaction Media
Further Information
Publication History
Received: 29 January 2015
Accepted after revision: 12 March 2015
Publication Date:
09 April 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201513/lookinside/thumbnails/ss-2015-h0067-op_10-1055_s-0034-1380523-1.jpg)
Abstract
A simple and highly efficient approach has been developed for a multicomponent one-pot reaction of aldehydes or ketones with amines and diethyl or triethyl phosphite to give the corresponding α-aminophosphonates. In the presence of quaternary ammonium salts, which are environmental friendly, inexpensive, and recyclable, α-aminophosphonates were obtained in excellent yields at room temperature within short times.
Key words
aminophosphonates - multicomponent reactions - quaternary ammonium salts - green chemistry - phosphorylationsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380523.
- Supporting Information
-
References
- 1 Peyman A, Budt K.-H, Spanig JS, Stowasser B, Ruppert D. Tetrahedron Lett. 1992; 33: 4549
- 2 Alonso E, Alonso E, Solis A, del Pozo C. Synlett 2000; 698
- 3 Kafarski P, Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991; 63: 193
- 4 Allerberger F, Klare IJ. J. Antimicrob. Chemother. 1999; 43: 211
- 5 Maier L. Phosphorus, Sulfur Silicon Relat. Elem. 1990; 47: 43
- 6 Maier L, Spörri H. Phosphorus, Sulfur Silicon Relat. Elem. 1991; 61: 69
- 7 Emsley J, Hall D. The Chemistry of Phosphorus: Environmental, Organic, Inorganic, Biochemical and Spectroscopic Aspects. Harper & Row; London: 1976
- 8 Chung S.-K, Kang D.-H. Tetrahedron: Asymmetry 1996; 7: 21
- 9a Kukhar VP, Solodenko VA. Russ. Chem. Rev. (Engl. Transl.) 1987; 56: 859
- 9b Laschat S, Kunz H. Synthesis 1992; 90
- 9c Matveeva ED, Podrugina TA, Tishkovskaya EV, Tomilova LG, Zefirov NS. Synlett 2003; 2321
- 9d Pavlov VY, Kabachnik MM, Zobnina EV, Timofeev VP, Konstantinov IO, Kimel BG, Ponomarev GV, Beletskaya IP. Synlett 2003; 2193
- 9e Van Meenen E, Moonen K, Acke D, Stevens CV. ARKIVOC 2006; (i): 31
- 9f Yadav JS, Reddy BV. S, Sreedhar P. Green Chem. 2002; 4: 436
- 9g Sobhani S, Safaei E, Asadi M, Jalili F. J. Organomet. Chem. 2008; 693: 3313
- 9h Dake SA, Raut DS, Kharat KR, Mhaske RS, Deshmukh SU, Pawar RP. Bioorg. Med. Chem. Lett. 2011; 21: 2527
- 9i Reddy CB, Kumar KS, Kumar MA, Reddy MV. N, Krishna BS, Naveen M, Arunasree MK, Reddy CS, Raju CN, Reddy CD. Eur. J. Med. Chem. 2012; 47: 553
- 9j Yu Y.-Q. Synthesis 2013; 45: 2545
- 9k Sharghi H, Ebrahimpourmoghaddam S, Doroodmand MM. Tetrahedron 2013; 69: 4708
- 9l Milen M, Ábrányi-Balogh P, Dancsó A, Frigyes D, Pongó L, Keglevich G. Tetrahedron Lett. 2013; 54: 5430
- 10a Kabachnik MI, Medved TY. Dokl. Akad. Nauk SSSR 1952; 83: 689
- 10b Fields EK. J. Am. Chem. Soc. 1952; 74: 1528
- 10c Keglevich G, Bálint E. Molecules 2012; 17: 12821
- 10d Zefirov NS, Matveeva ED. ARKIVOC 2008; (i): 1
- 11a Qian C, Huang T. J. Org. Chem. 1998; 63: 4125
- 11b Ranu BC, Hajra A, Jana U. Org. Lett. 1999; 1: 1141
- 11c Manabe K, Kobayashi S. Chem. Commun. 2000; 669
- 11d Chandrasekhar S, Prakash SJ, Jagadeshwar V, Narsihmulu C. Tetrahedron Lett. 2001; 42: 5561
- 11e Heydari A, Zarei M, Alijanianzadeh R, Tavakol H. Tetrahedron Lett. 2001; 42: 3629
- 11f Akiyama T, Sanada M, Fuchibe K. Synlett 2003; 1463
- 11g Xu F, Luo Y, Deng M, Shen Q. Eur. J. Org. Chem. 2003; 4728
- 11h Paraskar AS, Sudalai A. ARKIVOC 2006; (x): 183
- 11i Bhagat S, Chakraborti AK. J. Org. Chem. 2008; 73: 6029
- 11j Rezaei Z, Firouzabadi H, Iranpoor N, Ghaderi A, Jafari MR, Jafari AA, Zare HR. Eur. J. Med. Chem. 2009; 44: 4266
- 11k Thirumurugan P, Nandakumar A, Priya NS, Muralidaran D, Perumal PT. Tetrahedron Lett. 2010; 51: 5708
- 11l Gallardo-Macias R, Nakayama K. Synthesis 2010; 57
- 11m Tang J, Wang L, Wang W, Zhang L, Wu S, Mao D. J. Fluorine Chem. 2011; 132: 102
- 11n Disale ST, Kale SR, Kahandal SS, Srinivasan TG, Jayaram RV. Tetrahedron Lett. 2012; 53: 2277
- 11o Fang D, Jiao C, Ni C. Heteroat. Chem. 2010; 21: 546
- 11p Hou J.-T, Gao J.-W, Zhang Z.-H. Appl. Organomet. Chem. 2011; 25: 47
- 11q Zhang G, Zi Y, Xia Y, Fei Y, Wang Y. Huaibei Shifan Daxue Xuebao, Ziran Kexueban 2011; 32: 38
- 12a Yadav JS, Subba Reddy BV, Madan C. Synlett 2001; 1131
- 12b Kaboudin B, Nazari R. Tetrahedron Lett. 2001; 42: 8211
- 12c Kabachnik MM, Zobnina EV, Beletskaya IP. Synlett 2005; 1393
- 12d Xia M, Lu Y.-d. Ultrason. Sonochem. 2007; 14: 235
- 12e Zahouily M, Elmakssoudi A, Mezdar A, Rayadh A, Sebti S. Catal. Commun. 2007; 8: 225
- 12f Ambica SK, Taneja SC, Hundal MS, Kapoor KK. Tetrahedron Lett. 2008; 49: 2208
- 12g Bhattacharya AK, Rana KC. Tetrahedron Lett. 2008; 49: 2598
- 12h Dar B, Singh A, Sahu A, Patidar P, Chakraborty A, Singh B, Sharma M. Tetrahedron Lett. 2012; 53: 5497
- 12i Olszewski TK, Boduszek B. Tetrahedron 2010; 66: 8661
- 12j Ordóñez M, Sayago FJ, Cativiela C. Tetrahedron 2012; 68: 6369
- 12k Boduszek B, Olszewski TK, Goldeman W, Grzegolec K, Blazejewska P. Tetrahedron 2012; 68: 1223
- 12l Olszewski TK, Boduszek B. Synthesis 2011; 437
- 12m Tibhe GD, Bedolla-Medrano M, Cativiela C, Ordóñez M. Synlett 2012; 23: 1931
- 12n Michalska J, Boduszek B, Olszewski TK. Heteroat. Chem. 2011; 22: 617
- 13a Kassaee MZ, Movahedi F, Masrouri H. Synlett 2009; 1326
- 13b Vinu A, Kalita P, Balasubramanian VV, Oveisi H, Selvan T, Mano A, Chari MA, Subba Reddy BV. Tetrahedron Lett. 2009; 50: 7132
- 13c Subba Reddy BV, Siva Krishna A, Ganesh AV, Narayana Kumar GG. K. S. Tetrahedron Lett. 2011; 52: 1359
- 13d Kidwai M, Bhardwaj S, Mishra NK, Jain A, Kumar A, Mozzumdar S. Catal. Sci. Technol. 2011; 1: 426
- 13e Patil AB, Patil DS, Bhanage BM. Mater. Lett. 2012; 86: 50
- 14 Zon J. Pol. J. Chem. 1981; 55: 643
- 15a Sheykhan M, Mohammadnejad H, Akbari J, Heydari A. Tetrahedron Lett. 2012; 53: 2959
- 15b Fang D, Yang J, Ni C. Heteroat. Chem. 2011; 22: 5
- 15c Heydari A, Khaksar S, Tajbakhsh M. Tetrahedron Lett. 2009; 50: 77
- 15d Bhagat S, Chakraborti AK. J. Org. Chem. 2007; 72: 1263
- 15e Chandrasekhar S, Narsihmulu C, Sultana SS, Saritha B, Prakash SJ. Synlett 2003; 505
- 16a Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
- 16b Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA. Acc. Chem. Res. 1996; 29: 123
- 16c Ugi I. Pure Appl. Chem. 2001; 73: 187
- 16d Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439
- 16e Sunderhaus JD, Martin SF. Chem. Eur. J. 2009; 15: 1300
- 17 Multicomponent Reactions . Zhu J, Bienaymé H. Wiley-VCH; Weinheim: 2005
- 18a Welton T. Chem. Rev. 1999; 99: 2071
- 18b Welton T. Coord. Chem. Rev. 2004; 248: 2459
- 18c Sheldon R. Chem. Commun. 2001; 2399
- 18d Ionic Liquids in Synthesis . 2nd ed. Wasserscheid P, Welton T. Wiley-VCH; Weinheim: 2008
- 19a Luo SZ, Mi XL, Zhang L, Liu S, Xu H, Cheng J.-P. Angew. Chem. Int. Ed. 2006; 45: 3093
- 19b Ni B, Zhang QY, Headley AD. Green Chem. 2007; 9: 737
- 19c Ranu BC, Banerjee S. Org. Lett. 2005; 7: 3049
- 19d Xu J.-M, Qian C, Liu B.-K, Wu Q, Lin X.-F. Tetrahedron 2007; 63: 986
- 19e Xu J.-M, Wu Q, Zhang Q.-Y, Zhang F, Lin X.-F. Eur. J. Org. Chem. 2007; 1798
- 20a Zhou L, Wang L. Chem. Lett. 2007; 36: 628
- 20b Luo S, Mi X, Zhang L, Liu S, Xu H, Cheng J.-P. Tetrahedron 2007; 63: 1923
- 20c Hu S, Jiang T, Zhang Z, Zhu A, Han B, Song J, Xie Y, Li W. Tetrahedron Lett. 2007; 48: 5613
- 21a Feng L.-C, Sun Y.-W, Tang W.-J, Xu L.-J, Lam K.-L, Zhou Z, Chan AS. C. Green Chem. 2010; 12: 949
- 21b Sayin S, Yilmaz M. RSC Adv. 2014; 4: 2219
- 21c Petrović VP, Simijonović D, Živanović MN, Košarić JV, Petrović ZD, Marković S, Marković SD. RSC Adv. 2014; 4: 24635
- 22a Wasserscheid P, Sesing M, Korth W. Green Chem. 2002; 4: 134
- 22b Luo Y, Pan AX, Xing M, Chen M, Xie JM. Adv. Mater. Res. (Durnten-Zurich, Switz.) 2012; 443–444: 917
- 22c Tran PH, Duus F, Le TN. Tetrahedron Lett. 2012; 53: 222
- 23a Ying AG, Xu SL, Liu S, Ni YX, Yang JG, Wu CL. Ind. Eng. Chem. Res. 2014; 53: 547
- 23b Epishina MA, Ovchinnikov IV, Kulikov AS, Makhova NN, Tartakovsky VA. Mendeleev Commun. 2011; 21: 21
- 23c Li Z.-H, Zhou Z.-M, Hao X.-Y, Zhang J, Dong X, Liu Y.-Q, Sun W.-W, Cao D. Appl. Catal., A 2012; 425: 28
- 24 Xu D.-Z, Liu Y, Shi S, Wang Y. Tetrahedron: Asymmetry 2010; 21: 2530
- 25a Xu D.-Z, Liu Y, Shi S, Wang Y. Green Chem. 2010; 12: 514
- 25b Xu D.-Z, Shi S, Wang Y. RSC Adv. 2013; 3: 23075
- 26a Ying A, Li Z, Yang J, Liu S, Xu S, Yan H, Wu C. J. Org. Chem. 2014; 79: 6510
- 26b Safaei S, Mohammadpoor-Baltork I, Khosropour AR, Moghadam M, Tangestaninejad S, Mirkhani V. Adv. Synth. Catal. 2012; 354: 3095
- 26c Keithellakpam S, Laitonjam WS. Chin. Chem. Lett. 2014; 25: 767
- 26d Chiappe C, Rajamani S, D’Andrea F. Green Chem. 2013; 15: 137
- 26e Munshi MK, Gade SM, Rane VH, Kelkar AA. RSC Adv. 2014; 4: 32127
- 26f Singh A, Singh P, Goel N. Struct. Chem. 2014; 25: 821
- 26g Khalafi-Nezhad A, Mohammadi S. Synthesis 2012; 44: 1725
- 27 Hamadi H, Kooti M, Afshari M, Ghiasifar Z, Adibpour N. J. Mol. Catal. A: Chem. 2013; 373: 25
- 28 Agawane SM, Nagarkar JM. Tetrahedron Lett. 2011; 52: 3499
- 29 Pudovik AN. Izv. Akad. Nauk SSSR, Ser. Khim. 1952; 940