Abstract
Sonochemical oxidative-coupling of formamides with 1,3-dicarbonyl compounds in the corresponding carbamates by CuO nanoparticles as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant has been reported. Various derivatives of enol carbamates were synthesized with good to high yields under the optimized reaction conditions. Compared with conventional methods, the main advantage of this method is mild conditions.
Keywords: Ultrasound, oxidative-coupling, carbamates, CuO nanoparticles, TBHP, formamides.
Graphical Abstract
[1]
(a) Mason, T. J. Ultrason. Sonochem., 2007, 14, 476.
[http://dx.doi.org/10.1016/j.ultsonch.2006.10.008]
(b) Luche, J.L. Synthetic Organic Sonochemistry; Plenum Press: New York, 1998.
[http://dx.doi.org/10.1007/978-1-4899-1910-6]
[http://dx.doi.org/10.1016/j.ultsonch.2006.10.008]
(b) Luche, J.L. Synthetic Organic Sonochemistry; Plenum Press: New York, 1998.
[http://dx.doi.org/10.1007/978-1-4899-1910-6]
[2]
(a) Bremner, H. Ultrason. Sonochem., 1994, 1, S119.
[http://dx.doi.org/10.1016/1350-4177(94)90009-4]
(b) Boldyrev, V.V. Ultrason. Sonochem., 1995, 2, S143.
[http://dx.doi.org/10.1016/1350-4177(95)00019-3]
(c) Price, G. J. Ultrason. Sonochem., 2003, 10, 277.
[http://dx.doi.org/10.1016/S1350-4177(02)00156-6]
(d) Toma, S.; Gaplovsky, A. Luche. J. Ultrason. Sonochem., 2001, 8, 201.
[http://dx.doi.org/10.1016/S1350-4177(00)00073-0]
(e) Li, T.; Li, T.S.; Li, L.J.; Cheng, X. Ultrason. Sonochem., 1999, 6, 199.
[http://dx.doi.org/10.1016/S1350-4177(99)00014-0]
(f) Goharshadi, E.K.; Ding, Y.; Jorabchi, M.N.; Nancarrow, P. Ultrason. Sonochem., 2009, 16(1), 120-123.
[http://dx.doi.org/10.1016/j.ultsonch.2008.05.017] [PMID: 18640864]
(g) Rahman, N.M.A.; Saleh, T.S.; Mady, M.F. Ultrason. Sonochem., 2009, 16, 70.
[http://dx.doi.org/10.1016/j.ultsonch.2008.05.001] [PMID: 18567527]
[http://dx.doi.org/10.1016/1350-4177(94)90009-4]
(b) Boldyrev, V.V. Ultrason. Sonochem., 1995, 2, S143.
[http://dx.doi.org/10.1016/1350-4177(95)00019-3]
(c) Price, G. J. Ultrason. Sonochem., 2003, 10, 277.
[http://dx.doi.org/10.1016/S1350-4177(02)00156-6]
(d) Toma, S.; Gaplovsky, A. Luche. J. Ultrason. Sonochem., 2001, 8, 201.
[http://dx.doi.org/10.1016/S1350-4177(00)00073-0]
(e) Li, T.; Li, T.S.; Li, L.J.; Cheng, X. Ultrason. Sonochem., 1999, 6, 199.
[http://dx.doi.org/10.1016/S1350-4177(99)00014-0]
(f) Goharshadi, E.K.; Ding, Y.; Jorabchi, M.N.; Nancarrow, P. Ultrason. Sonochem., 2009, 16(1), 120-123.
[http://dx.doi.org/10.1016/j.ultsonch.2008.05.017] [PMID: 18640864]
(g) Rahman, N.M.A.; Saleh, T.S.; Mady, M.F. Ultrason. Sonochem., 2009, 16, 70.
[http://dx.doi.org/10.1016/j.ultsonch.2008.05.001] [PMID: 18567527]
[3]
(a) Hartley, D.; Kidd, H. The Agrochemicals Handbook; Royal Society of Chemistry: Cambridge, 1991.
(b) Nasr, M.; Paull, K.D.; Narayanan, V.L. J. Pharm. Sci., 1985, 74(8), 831-836.
[http://dx.doi.org/10.1002/jps.2600740806] [PMID: 4032265]
(c) Adams, P.; Baron, F.A. Chem. Rev., 1965, 65, 567-602.
[http://dx.doi.org/10.1021/cr60237a002]
(d) Tai-The, W.; Huang, J.; Arrington, N.D.; Dill, G.M. J. Agric. Food Chem., 1987, 35, 817-823.
[http://dx.doi.org/10.1021/jf00077a044]
(e) Vauthey, I.; Valot, F.; Gozzi, C.; Fache, F.; Lemaire, M. Tetrahedron Lett., 2000, 41, 6347-6350.
[http://dx.doi.org/10.1016/S0040-4039(00)01051-0]
(f) Angeles, E.; Martinez, P.; Keller, J.; Martinez, R.; Rubio, M. Ram_rez, G.; Castillo, R.; Lopez- Castanares, R.; Jimenez, E. J. Mol. Struct. THEOCHEM, 2000, 504, 141-170.
[http://dx.doi.org/10.1016/S0166-1280(00)00361-4]
(b) Nasr, M.; Paull, K.D.; Narayanan, V.L. J. Pharm. Sci., 1985, 74(8), 831-836.
[http://dx.doi.org/10.1002/jps.2600740806] [PMID: 4032265]
(c) Adams, P.; Baron, F.A. Chem. Rev., 1965, 65, 567-602.
[http://dx.doi.org/10.1021/cr60237a002]
(d) Tai-The, W.; Huang, J.; Arrington, N.D.; Dill, G.M. J. Agric. Food Chem., 1987, 35, 817-823.
[http://dx.doi.org/10.1021/jf00077a044]
(e) Vauthey, I.; Valot, F.; Gozzi, C.; Fache, F.; Lemaire, M. Tetrahedron Lett., 2000, 41, 6347-6350.
[http://dx.doi.org/10.1016/S0040-4039(00)01051-0]
(f) Angeles, E.; Martinez, P.; Keller, J.; Martinez, R.; Rubio, M. Ram_rez, G.; Castillo, R.; Lopez- Castanares, R.; Jimenez, E. J. Mol. Struct. THEOCHEM, 2000, 504, 141-170.
[http://dx.doi.org/10.1016/S0166-1280(00)00361-4]
[4]
(a) Green, T.W.; Wuts, P.G.M. Protecting Groups in Organic Synthesis, 2nd ed; Wiley: New York, 1999.
[http://dx.doi.org/10.1002/0471220574]
(b) Caroino, L.A. Acc. Chem. Res., 1973, 6, 191-198.
[http://dx.doi.org/10.1021/ar50066a003]
(c) Xiuo, X. Yi.; Ngu, K.; Choa, C.; Patel, D.V. J. Org. Chem., 1997, 62, 6968-6973.
[http://dx.doi.org/10.1002/0471220574]
(b) Caroino, L.A. Acc. Chem. Res., 1973, 6, 191-198.
[http://dx.doi.org/10.1021/ar50066a003]
(c) Xiuo, X. Yi.; Ngu, K.; Choa, C.; Patel, D.V. J. Org. Chem., 1997, 62, 6968-6973.
[5]
Yadav, J.S.; Reddy, G.S.; Reddy, M.M.; Meshram, H.M. Tetrahedron Lett., 1998, 39, 3259-3262.
[http://dx.doi.org/10.1016/S0040-4039(98)00464-X]
[http://dx.doi.org/10.1016/S0040-4039(98)00464-X]
[6]
Angeles, E.; Santillan, A.; Martinez, I.; Ramirez, A.; Moreno, E.; Salmon, M.; Martinez, R. Synth. Commun., 1994, 24, 2441-2447.
[http://dx.doi.org/10.1080/00397919408010552]
[http://dx.doi.org/10.1080/00397919408010552]
[7]
Kocovsky, P. Tetrahedron Lett., 1986, 27, 5521-5524.
[http://dx.doi.org/10.1016/S0040-4039(00)85256-9]
[http://dx.doi.org/10.1016/S0040-4039(00)85256-9]
[8]
(a) Ragaini, F.; Cenini, S. Organometallics, 1994, 13, 1178-1189.
[http://dx.doi.org/10.1021/om00016a022]
(b) Paul, F.; Fischer, J.; Ochsenbein, P.; Osborn, J.A. Organometallics, 1998, 17, 2199-2206. [and references cited therein]
[http://dx.doi.org/10.1021/om9708485]
(c) Cenini, S.; Crotti, C.; Pizzoti, M.; Porta, F. J. Org. Chem., 1988, 53, 1243-1250.
[http://dx.doi.org/10.1021/jo00241a023]
(d) Shi, F.; Deng, Y. Chem. Commun. (Camb.), 2001, 443-444.
[http://dx.doi.org/10.1039/b009575n]
(e) Leung, T.W.; Dombek, B.D. J. Chem. Soc. Chem. Commun., 1992, 205-206.
[http://dx.doi.org/10.1039/c39920000205]
(f) Alper, H.; Hartstock, F.W. J. Chem. Soc. Chem. Commun., 1985, 1141-1142.
[http://dx.doi.org/10.1039/c39850001141]
(g) Fukuoka, S.; Chono, M.; Kohno, M. J. Chem. Soc. Chem. Commun., 1984, 399-400.
[http://dx.doi.org/10.1039/c39840000399]
[http://dx.doi.org/10.1021/om00016a022]
(b) Paul, F.; Fischer, J.; Ochsenbein, P.; Osborn, J.A. Organometallics, 1998, 17, 2199-2206. [and references cited therein]
[http://dx.doi.org/10.1021/om9708485]
(c) Cenini, S.; Crotti, C.; Pizzoti, M.; Porta, F. J. Org. Chem., 1988, 53, 1243-1250.
[http://dx.doi.org/10.1021/jo00241a023]
(d) Shi, F.; Deng, Y. Chem. Commun. (Camb.), 2001, 443-444.
[http://dx.doi.org/10.1039/b009575n]
(e) Leung, T.W.; Dombek, B.D. J. Chem. Soc. Chem. Commun., 1992, 205-206.
[http://dx.doi.org/10.1039/c39920000205]
(f) Alper, H.; Hartstock, F.W. J. Chem. Soc. Chem. Commun., 1985, 1141-1142.
[http://dx.doi.org/10.1039/c39850001141]
(g) Fukuoka, S.; Chono, M.; Kohno, M. J. Chem. Soc. Chem. Commun., 1984, 399-400.
[http://dx.doi.org/10.1039/c39840000399]
[9]
Kianmehr, E.; Baghersad, M.H. Adv. Synth. Catal., 2011, 353, 2599-2603.
[http://dx.doi.org/10.1002/adsc.201100153]
[http://dx.doi.org/10.1002/adsc.201100153]
[10]
Kumar, G.S.; Maheswari, C.U.; Kumar, R.A.; Kantam, M.L.; Reddy, K.R. Angew. Chem. Int. Ed., 2011, 50, 11748-11751.
[http://dx.doi.org/10.1002/anie.201105020]
[http://dx.doi.org/10.1002/anie.201105020]
[11]
(a) Barve, B.D.; Wu, Y.-C.; El-Shazly, M.; Chuang, D.-W.; Chung, Y.-M.; Tsai, Y.-H.; Wu, S.-F.; Korinek, M.; Du, Y.-C.; Hsieh, C.-T.; Wang, J.-J.; Chang, F.-R. Eur. J. Org. Chem., 2012, 6760-6766.
[12]
(a) Saberi, D.; Heydari, A. Tetrahedron Lett., 2013, 54, 4178-4180.
[http://dx.doi.org/10.1016/j.tetlet.2013.05.113]
(b) Saberi, D.; Mansoori, S.; Ghaderi, E.; Niknam, Kh. Tetrahedron Lett., 2016, 57, 95-99.
[http://dx.doi.org/10.1016/j.tetlet.2015.11.072]
[http://dx.doi.org/10.1016/j.tetlet.2013.05.113]
(b) Saberi, D.; Mansoori, S.; Ghaderi, E.; Niknam, Kh. Tetrahedron Lett., 2016, 57, 95-99.
[http://dx.doi.org/10.1016/j.tetlet.2015.11.072]
[13]
(a) Akbari, J.; Heydari, A.; Reza Kalhor, H.; Kohan, S.A. J. Comb. Chem., 2010, 12(1), 137-140.
[http://dx.doi.org/10.1021/cc9001313] [PMID: 19883051]
(b) Nouri, A.; Akbari, J.; Heydari, A.; Nouri, A. Lett. Org. Chem., 2011, 11, 38.
[http://dx.doi.org/10.2174/157017811794557859]
(c) Akbari, J.; Sajirani, S.B.; Nejad, M. J.; Heydari, A., Lett. Org. Chem., 2012, 9, 165.
[http://dx.doi.org/10.2174/157017812800167510]
(d) Akbari, J.; Heydari, A., Curr NanoScience., 2012, 8, 398.
[http://dx.doi.org/10.2174/157341312800620205]
(e) Farahani, N.; Akbari, J. Lett. Org. Chem., 2017, 14, 483.
[http://dx.doi.org/10.2174/1570178614666170321123731]
[http://dx.doi.org/10.1021/cc9001313] [PMID: 19883051]
(b) Nouri, A.; Akbari, J.; Heydari, A.; Nouri, A. Lett. Org. Chem., 2011, 11, 38.
[http://dx.doi.org/10.2174/157017811794557859]
(c) Akbari, J.; Sajirani, S.B.; Nejad, M. J.; Heydari, A., Lett. Org. Chem., 2012, 9, 165.
[http://dx.doi.org/10.2174/157017812800167510]
(d) Akbari, J.; Heydari, A., Curr NanoScience., 2012, 8, 398.
[http://dx.doi.org/10.2174/157341312800620205]
(e) Farahani, N.; Akbari, J. Lett. Org. Chem., 2017, 14, 483.
[http://dx.doi.org/10.2174/1570178614666170321123731]
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
Article Metrics
12