Ali RAMAZANI, Kourosh DASTANRA, Fatemeh Zeinali NASRABADI

Silica nanoparticles as a high efficient catalyst for the one-pot synthesis of 3-oxo-3-phenylpropanamid derivatives from isocyanides, phenylacetaldehyde and secondary amines

Reaction of an isocyanide with an iminium ion intermediate, formed by reaction between 2-oxo-2-phenylacetaldehyde and a secondary amine in the presence of silica nanoparticles, proceeds smoothly at room temperature to afford ketoamide derivatives in high yields.

Anahtar Kelimeler:

Silica nanoparticles, multicomponent reaction, isocyanide, 2-oxo-2-phenylacetaldehyde, secondary amine, iminium ion

Silica nanoparticles as a high efficient catalyst for the one-pot synthesis of 3-oxo-3-phenylpropanamid derivatives from isocyanides, phenylacetaldehyde and secondary amines

Keywords:

Silica nanoparticles, multicomponent reaction, isocyanide, 2-oxo-2-phenylacetaldehyde, secondary amine, iminium ion,

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Orru, R. V. A.; Greef, M. Synthesis 2003, 1471-1499.
Ramazani, A.; Shajari, N.; Mahyari, A.; Ahmadi, Y. Mol. Divers 2011, 15, 521-527
Zeinali Nasrabadi, F.; Ramazani, A.; Ahmadi, Y. Mol. Divers 2011, 15, 791-798
Ramazani, A.; Zeinali Nasrabadi, F.; Mashhadi Malek Zadeh, A.; Ahmadi, Y. Monatsh. Chem. 2011, 142, 625-630
Ramazani, A.; Kazemizadeh, A. R. Curr. Org. Chem. 2011 15, 3986-4020.
Trost, B. M.; Acc. Chem. Res. 2002, 35, 695-705
Ugi, I.; Werner, B.; D¨omling, A. Molecules 2003, 8, 53-66
Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem. Int. Ed. 2005, 44, 7852-7872.
Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
Lewis, L. N. Chem. Rev. 1993, 93, 2693-2730.
Banerjee, S.; Santra, S. Tetrahedron Lett. 2009, 50, 2037-2040.
Stefane, B.; Polanc, S. Tetrahedron. 2007, 63, 10902-10913.
Gotor, V.; Liz, R.; Testera, A. Tetrahedron. 2004, 60, 607-618.
Sibi, M.; Christensen, J.; Kim, S.; Eggen, M.; Stessman, C.; Oien, L. Tetrahedron Lett. 1995, 36, 6209-6212.
Ramazani, A.; Azizian, A.; Bandpey, M.; Noshiranzadeh, N. Phosphorus, Sulfur, Silicon Relat. Elem. 2006, 181, 2734.
Yavari, I.; Ramazani, A. Phosphorus, Sulfur, Silicon Relat. Elem. 1997, 130, 73-77.
Ramazani, A.; Bodaghi, A. Tetrahedron Let t. 2000, 4 1, 567-568
Ramazani, A.; Ahmadi, Y.; Rouhani, M.; Shajari, N.; Souldozi, A. Heteroat. Chem 2010, 21, 368-372
Ramazani, A.; Ahmadi, Y.; Tarasi, R. Heteroat. Chem. 2011, 22, 79-84
Souldozi, A.; Ramazani, A; Bouslimani, N; Welter, R. Tetrahedron Lett. 2007, 48, 2617-2620.
Souldozi, A.; Ramazani, A. Tetrahedron Lett. 2007, 48, 1549-1551.
Yavari, I.; Ramazani, A; Yahya-Zadeh, A. Synth. Commun. 1996, 26, 4495-4499.
Pakravan, P.; Ramazani, A.; Noshiranzadeh, N.; Sedrpoushan, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2007, , 545-549.
Ramazani, A.; Rahimifard, M.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2007, 182, 1-5.
Ramazani, A.; Rahimifard, M.; Noshiranzadeh, N.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2007 413-417.
Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, 17 8, 2663-2666
Ramazani, A.; Shajari, N.; Gouranlou, F. Phosphorus, Sulfur, Silicon Relat. Elem 2001 174, 223-227.
Ramazani, A.; Mahyari, A. T; Rouhani, M.; Rezaei, A. Tetrahedron Lett. 2009, 50, 5625-5627.
Kazemizadeh, A. R.; Ramazani, A. J. Braz. Chem. Soc. 2009, 20, 309-312.
Ramazani, A.; Amini, I.; Massoudi, A. Phosphorus, Sulfur, Silicon Relat. Elem 2006, 181 2225-2229.
Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, 178, 1325-1328.
Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, 178, 1329-1332.
Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2009, 184, 3191-3198.
Souldozi, A.; Ramazani, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2009, 184, 2344-2350.
Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2004, 179, 529-534.
Ramazani, A.; Bodaghi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2004, 179, 1615-1620
Ramazani, A.; Mahyari, A.; Farshadi, A.; Rouhani, M. Helv. Chim. Acta 2011, 94 1831-1837.
Heshmati-Gonbari, M.; Ramazani, A; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2009, 184, 309-314. a) Ramazani, A; Rezaei, A. Org. Let t. 2010, 12, 2852-2855;b) Ramazani, A.; Karimi, Z.; Souldozi, A.; Ahmadi, Y.
Turk. J. Chem. 2012, 36 81-91; c) Valizadeh Holagh, M.; Maharramov, A. M.; Allahverdiyev, M. A.; Ramazani,
A.; Ahmadi, Y.; Souldozi, A.; Turk. J. Chem. 2012, 36 179-188; d) Ramazani, A.; Ahmadi, Y.; Mahyari, A.
Synthetic Commun. 2011, 41, 2273-2282; e) Ramazani, A.; Nasrabadi, F. Z.; Ahmadi, Y. Helv. Chim. Acta 2011, , 1024-1029; f) Ramazani, A.; Ahmadi, Y.; Nasrabadi, F. Z. Z. Naturforsch 2011, 66b, 184-190; g) Souldozi,
A.; Ramazani, A. Arkivoc 2008, xvi, 235-242; h) Ramazani, A.; Rouhani, M.; Rezaei, A.; Shajari, N.; Souldozi, A.
Helv. Chim. Acta 2011, 94, 282-288; i) Shajari, N.; Ramazani, A.; Ahmadi, Y. Bull. Chem. Soc. Ethiop. 2011, 25, 6; j) Ramazani, A.; Nasrabadi, F. Z.; Karimi, Z.; Rouhani, M. Bull. Korean Chem. Soc. 2011, 32, 2700-2704; k)
Ramazani, A.; Farshadi, A.; Mahyari, A.; ´Slepokura, K.; Lis, T.; Rouhani, M.; J. Chem. Crystallogr. 2011, 41, 1385; l) Massoudi, A.; Amini, I.; Ramazani, A.; Nasrabadi, F. Z.; Ahmadi, Y. Bull. Korean Chem. Soc. 2012, , 39-42; m) Ramazani, A.; Rezaei, A; Ahmadi, Y. Phosphorus, Sulfur, Silicon Relat. Elem 2012, 187, 22-31; n)
Ramazani, A.; Momeni-Movahhed, A.; Gouranlou, F. Phosphorus, Sulfur, Silicon Relat. Elem 2002, 177, 903-907; o) Kazemizadeh, A. R.; Ramazani, A. Arkivoc 2008, xv, 159-165
Ramazani, A.; Noshiranzadeh, N.; Ghamkhari, A.; ´Slepokura, K; Lis, T. Helv. Chim. Acta. 2008, 91, 2252-2261
Ramazani, A.; Rezaei, A; Mahyari, A. T; Rouhani, M.; Khoobi, M. Helv. Chim. Acta. 2010, 93, 2033-2036.
Ramazani, A.; Mahyari, A. Helv. Chim. Act a. 2010, 93, 2203-2209
Ramazani, A., Mahyari, A; Lashgari, H; ´Slepokura, K; Lis, T. Helv. Chim. Acta. 2011, 94,611-622. de Souzaa, M. F.; Batistaa, P. S.; Regiania, I.; Liboriob, J. B. L.; de Souzac, D. P. F. Mater. Res. 2000, 3, 25-30.