Scopus (CiteScore 2022 =3.0, Q3) , ISC

Document Type : Original Research Article

Authors

1 Department of Chemistry, University of Zanjan, P.O. BOX 45195-313, Zanjan,

2 Research Institute of Modern Biological Techniques (RIMBT), University of Zanjan, P.O. BOX 45195-313, Zanjan, Iran

Abstract

Kabachnik-Fields reaction between an amine, quinoline-4-carbaldehyde, and a phosphite in the presence of the prepared silica nanoparticles from rice hulls  (silica NP; ca. 42 nm) proceeds smoothly to afford the corresponding α-aminophosphonates in high yields. The reactions were carried out in one pot and under solvent-free conditions at 50-80 ˚C.

Graphical Abstract

Silica nanoparticles as highly efficient catalyst for the one-pot synthesis of α-aminophosphonate derivatives from primary amines, quinoline-4-carbaldehyde and phosphite under solvent-free conditions

Keywords

[1]  R.P.J. Sheridan, Chem. Inf. Comput. Sci., 2002, 42, 103-108.
[2] (a) P. Kafarski, B. Lejczak, Phosphorus, Sulfur Silicon Relat. Elem., 1991, 63, 193-215. (b) X. J. Mu, M.Y. Lei, J.P. Zou, W. Zhang, Tetrahedron Lett., 2006, 47, 1125-1127. (c) J. Grembecka, A. Mucha, T. Cierpicki, P. Kafarski, J. Med. Chem., 2003, 46, 2641-2655. (d) J.D. Moore, K.T. Sprott, A.J. Fisher, M. Tony, Biochemistry. 2002, 67, 8123-8129. (e) W. Liu, C.J. Rogers, A.J. Fisher, M. Toney, Biochemistry., 2002, 41, 12320-12328. (f) S.N. Osipov, O.I. Artyushin, A.F. Kolomeits, C. Bruneau, P.H. Dixneuf, Synlett. 2000, 7, 1031-1033. (g) E.K. Baylis, C.D.Campbell, J.G.  Dingwall, J. Chem. Soc., Perkin Trans.1., 1984, 2845-2853.
[3] (a) V.P. Kukhar, H.R. Hudson, In Aminophosphonic and Aminophosphinic Acids; John Wiley & Sons: Chichester, 2000. (b) B. Kaboudin, Phosphorus, Sulfur Silicon., 2002, 177, 1749–1751.
[4]  (a) T. Yokomatsu, Y. Yoshida, S. Shibuya, J. Org. Chem., 1994, 59, 7930-7933. (b) V.P. Kukhar', V. Solodenko, Russ. Chem. Rev., 1987, 56, 859-874. (c) S. Bhagat, A. Chakraborti,  J. Org. Chem., 2007, 72, 1263-1270. (d) F. Palacios, J. Vicario, A. Maliszewska, D. Aparicio, J. Org. Chem., 2007, 72, 2682-2685. (e) S. Chandrasekhar, S. Prakhash, V. Jagadeshwar, C. Narsihmulu, Tetrahedron Lett., 2001, 42, 5561-5563. (f) K. Manabe, S. Kobayashi, Chem. Commun., 2000, 669-670.
[5]  (a) M.J. Kabachnik, T. Medved, Izv. Akad. Nauk SSSR, 1953, 8, 1126-1128. (b) M.J. Kabachnik, T. Medved, Izv. Akad. Nauk SSSR, 1954, 1024. (c) E.K. Fields, J. Am. Chem. Soc., 1952, 74, 1528-1531. (d) K.A. Petrov, V.A. Chauzov, T.S. Erokhina, Russ. Chem. Rev., 1974, 43, 984-1006.
[6]  (a) S. Bhagat, A.K. Chakraborti, J. Org. Chem., 2007, 72, 1263-1270. (b) M.R. Saidi, N. Azizi, Synlett., 2002, 2002, 1347-1349. (c) N. Azizi, F. Rajabi, M.R. Saidi, Tetrahedron Lett., 2004, 45, 9233-9236. (d) B.C. Ranu, A. Hajra, U. Jana, Org. Lett., 1999, 1, 1141-1143. (e) I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1., 2001, 2804-2816. (f) A. Manjula, B. Vittal Rao, P. Neelakantan, Synth. Commun., 2003, 33, 2963-2969. (g) S. Laschat, H. Kunz, Synthesis, 1992, 1, 90-95.
[7]  F. Texier-Boullet, M. Lequitte, Tetrahedron Lett., 1986, 27, 3515-3516.
[8]  V.J. Blazis, K.J. Koeller, C.D. Spilling, J. Org. Chem., 1995, 60, 931-940.
[9]  A. Sardarian, B. Kaboudin, Synth. Commun., 1997, 27, 543-551.
[10] (a) C. Qian, T. Huang, J. Org. Chem., 1998, 63, 4125-4128. (b) S. Chanrasekhar, S. Prakash, V.   Jagadeshwar, C. Narsihmulu, Tetrahedron Lett., 2001, 42, 5561-5563.
[11]  (a) D. Astruc, F. Lu, J.R. Aranzaes, Angew. Chem. Int. Ed., 2005, 44, 7852-7872. (b) I.P. Beletskaya, A.V. Cheprakov, Chem. Rev., 2000, 100, 3009-3066. (c) H. Saeidian, H. Sadighian, M. Arabgari, Z. Mirjafary, S.E. Ayati, E. Najafi, F. Matloubi Moghaddam, Res. Chem. Intermed., 2018, 44, 601-612. (d) Z. Arzehgar, A. Aydi, M. M. Heydari, Asian J. of Green Chem., 2018, 281-298. (e)  H. Saeidian, S. Vahdati Khajeh, Z. Mirjafary, B. Eftekhari-Sis, RSC Advances, 2018, 8, 38801-38807.
[12]  (a) L.N. Lewis, Chem. Rev., 1993, 93, 2693-2730. (b) S. Banerjee, S. Santra, Tetrahedron Lett., 2009, 50, 2037-2040. (c) F. Matloubi Moghaddam, M. Doulabi, H. Saeidian, Scientia Iranica, 2012, 19, 1597-1600. (d) N. Rasouli, M. Movahedi, E. Aghabeikzadeh Naeini, Iran. Chem. Commun., 2018, 6, 169-179. (e) H. Saeidian, F. Matloubi Moghaddam, A. Pourjavadi, Sh. Barzegar, R. Soleyman, A. Sohrabi, J. Braz. Chem. Soc., 2009, 20, 466-471.
[13]  (a) M.F. De Souzaa, P.S.  Batistaa, I. Regiania, J.B.L. Liboriob, D.P.F.  de Souzac, Mater. Res., 2000, 3, 25-30. (b) A. Ramazani, A. Mahyari, Helv. Chim. Acta., 2010, 93, 2203-2209.
[14]  A. Ramazani, Y. Ahmadi, H. Aghahosseini, S. Woo Joo, Phosphorus, Sulfur Silicon Relat. Elem., 2016, 191, 354-358.
[15]  A. Ramazani, Y. Ahmadi, N. Fattahi, H. Ahankar, M. Pakzad, H. Aghahosseini, A. Rezaei, S. Taghavi Fardood, S. Woo Joo, Phosphorus, Sulfur Silicon Relat. Elem., 2016, 191, 1057-1062.
[16]  A. Ramazani, F. Zeinali Nasrabadi, H. Ahankar, P. Azimzadeh Asiabi, F. Sadri, S. Woo Joo, Phosphorus, Sulfur Silicon Relat. Elem., 2016, 191, 230-234.
[17]  A. Ahmadi, A. Bagherzadeh, A. Ramazani, Y. Ahmadi, S. Woo Joo, H. Ahankar, Phosphorus, Sulfur Silicon Relat. Elem., 2016, 191, 871-875.
[18]  A. Jafari, A. Ramazani, H. Ahankar, P. Azimzadeh Asiabi, F. Sadri, S. Woo Joo, Phosphorus, Sulfur Silicon Relat. Elem., 2016, 191, 373-380. 
[19] J. Taran, A. Ramazani, H. Aghahosseini, F. Gouranlou, R. Tarasi, M. Khoobi, S.W. Joo, Phosphorus, Sulfur Silicon Relat. Elem., 2017, 192, 776-781
[20] (a) A.N. Pudovik, Dokl Akad Nauk SSSR. 1952, 83, 865-868. (b) M. I. Kabachnik, T. Ya.   Medved, Dokl. Akad. Nauk SSSR. 1952, 83, 689.
[21] (a) W. Abramov, Dokl Akad Nauk SSSR. 1950, 73, 487-489. (b) C. Rafael'A, V.I. Galkin, Russ. Chem. Rev. 1998, 67, 857-882.
[22] (a) I. Galkina, E. Zvereva, V. Galkin, R. Cherkasov, Zh. Obshch. Khim., 1998, 68, 1457-1464. (b) I. Galkina, A. Sobanov, V. Galkin, R. Cherkasov, Zh. Obshch. Khim., 1998, 68, 1465-1468. (c) M.N. Dimukhametov, M.A. Abaskalova, E.Y. Davydova, E.V. Bayandina, A.B. Dobrynin, I.A. Litvinov, V.A. Alfonsov, Mendeleev Commun., 2004, 14, 35-37.