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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Microwave-Assisted Synthesis of Chiral Oxime Ethers

Author(s): Asma Mehrez*, Dalila Mtat and Ridha Touati

Volume 16, Issue 6, 2019

Page: [495 - 500] Pages: 6

DOI: 10.2174/1570178615666181106125853

Price: $65

Abstract

An efficient and rapid synthesis of a new class of chiral oxime ethers has been achieved via two-step reaction in which the first step is the reaction of oximes 1a-f with ethyl bromoacetate in the presence of sodium hydride to give oxime ethers 2a-f which are subsequently, in the second step, reacted with different commercially available chiral amines under microwave irradiation conditions to give compounds 3a-l in good to excellent yields. Through this method, we have observed a decrease in reaction time and excellent yields than the previously described conventional method.

Keywords: Oxime ethers, chiral, achiral, microwave irradiation, biological activity, growth regulators.

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[1]
Esmail, V.; Morteza, A. J. Iran. Chem. Soc., 2016, 13, 1235-1256.
[2]
Smith, P.W.; Chamiec, A.J.; Chung, G.; Cobley, K.N.; Duncan, K.; Howes, P.D.; Whittington, A.R.; Wood, M.R. J. Antibiot., 1996, 48, 73-82.
[3]
(a) Declerk, F.; Beetens, J.; Van de Water, A.; Vercammen, E.; Janssen, P.A.J. Thromb. Haemostasis., 1989, 61, 43-49.
(b) Bossche, H.V.; Willemsens, G.; Bellens, D.; Janssen, P.A. J. Biochem. Pharmacol., 1992, 43, 739-744.
[4]
Brouwer, M.S.; Grosscurt, A.C.U.S. Patent, 4609, 676, , 1986.
[5]
Wahbi, Y.; Caujolle, R.; Tournaire, C.; Payard, M.; Linas, M.D.; Seguela, J.P. Eur. J. Med. Chem., 1995, 30, 955-962.
[6]
Mordi, M.N.; Pelta, M.D.; Boote, V.; Morris, G.A.; Barber, J. J. Med. Chem., 2000, 43, 467-474.
[7]
Gharbi-Benarous, J.; Delaforge, M.; Jankowski, C.K.; Girault, J.P. J. Med. Chem., 1991, 34, 1117-1125.
[8]
Dijk, J.V.; Zwagemakers, J.M.A. J. Med. Chem., 1977, 20, 1199-1206.
[9]
(a) Phillpotts, R.J.; Delong, D.C.; Wallace, J.; Jones, R.W.; Reed, S.E.; Tyrrell, D.A. Lancet, 1981, 1, 1342-1344.
(b) Hayden, F.G.; Gawaltney, J.M. J. Antimicrob. Agents Chemother., 1982, 21, 892-897.
[10]
(a)Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances, 3rd ed; George Thieme Verlag: Stuttgart, New York, 1999, p. 2286.
(b) Kassa, J. Clin. Toxicol., 2002, 40, 803-816.
[11]
Yang, G.Y.; Yoon, J.H.; Seong, C.M.; Park, N.S.; Jung, Y.S. Bull. Korean Chem. Soc., 2003, 24, 1368-1370.
[12]
Adrivan, D.H.; Jan, H.V.M.; Andrew, C.M.; Arie, T.M.; Guus, J.M.S.; Herman, H.S.; Theo, J.J.Z.; Barbara, Z.; Wouter, I.B. Biol. Med. Chem. Lett., 2006, 16, 1045-1048.
[13]
ZeKai H.; HaiLei, C.; Kun, J.; Ying, C.C. Sci. China Series B Chem., 2009, 52, 1309-1313.
[14]
Vanderwal, C.D.; Jacobsen, E.N. J. Am. Chem. Soc., 2004, 126, 14724-14725.
[15]
Chang, L.; Shang, D.J.; Xin, J.G.; Liu, X.H.; Feng, X.M. Tetrahedron Lett., 2008, 49, 6663-6666.
[16]
Dinér, P.; Nielsen, M.; Bertelsen, S.; Niess, B.; Jørgensen, K.A. Chem. Commun., 2007, 35, 3646-3648.
[17]
Bertelsen, S.; Dinér, P.; Johansen, R.L.; Jørgensen, K.A. J. Am. Chem. Soc., 2007, 129, 1536-1537.
[18]
Carlone, A.; Bartoli, G.; Bosco, M.; Pesciaioli, F.; Ricci, P.; Sambri, L.; Melchiorre, P. Eur. J. Org. Chem., 2007, 3, 5492-5495.
[19]
(a) Abele, E.; Abele, R.; Rubina, K.; Popelis, J.; Sleiksa, I.; Lukevics, E. Synth. Commun., 1998, 28, 2621.
(b) Yamada, T. Goto. K.; Mitsuda, Y.; Tsuji, J. Tetrahedron Lett., 1987, 28, 4557-4560.
(c) Karakurt, A.; Dalkara, S.; Özalp, M.; Özbey, S.; Kendi, E.; Stables, J.P. Eur. J. Med. Chem., 2001, 36, 421-433.
(d) Merkaš, S.; Litvić, M.; Cepanec, I.; Vinković, V. Molecules, 2005, 10, 1429-1437.
(e) Abele, E.; Lukevics, E. Org. Prep. Proced. Int., 2000, 32, 235-264.
(f) Banerjee, T.; Dureja, P. Molecules, 2005, 10, 990-999.
(g) Li, C.B.; Zhang, H.; Cui, Y.; Zhang, S.; Zhao, Z.; Choi, M.C.K.; Chan, A.S.C. Synth. Commun., 2003, 3, 543-546.
[20]
(a) Nanoppa, P.D.; Pandurangan, K.; Maitra, U.; Wailes, S. Org. Lett., 2007, 9, 2767-2770.
(b) Mooradian, A.; Dupont, P.E.J. Heterocycl. Chem, 1967, 4, 441-444.
[21]
(a) Jacob, B.B. Synthesis, 1975, 782.
(b) Nesynov, E.P.; Pel’kis, P.S. Zh. Org. Khim., 1976, 12, 1955.
[22]
(a) Miyabe, H.; Yoshida, K.; Reddy, V.K.; Matsumura, A.; Takemoto, Y. J. Org. Chem., 2005, 70, 5630-5635.
(b) Miyabe, H.; Matsumura, A.; Yoshida, K.; Yamauchi, M.; Takemoto, Y. Synlett, 2004, 12, 2123-2126.
(c) Miyabe, H.; Matsumura, A.; Moriyama, K.; Takemoto, Y. Org. Lett., 2004, 6, 4631-4634.
[23]
Stefani, A.P.; Lacher, J.R.; Park, J.D. J. Org. Chem., 1960, 25, 676.
[24]
(a) Bhuniya, D.; Mohan, S.; Narayanan, S. Synthesis, 2003, 7, 1018.
(b) Bertelsen, S.; Dinér, P.; Johansen, R.L.; Jørgensen, K.A. J. Am. Chem. Soc., 2007, 129, 1536.
(c) Vanderwal, C.D.; Jacobsen, E.N. J. Am. Chem. Soc., 2004, 126, 14724.
(d) Fouchet, B.; Joucla, M.; Messager, J.C.; Toupet, L. J. Chem. Soc., 1982, 858.
(e) Bhuniya, D.; Gujjary, S.; Sengupta, S. Synth. Commun., 2006, 36, 151.
[25]
Kolenc, I.; Kocevar, M.; Polanc, S. Acta Chim. Slov., 1999, 46, 281-288.
[26]
(a) Timothy, E.H.; Timothy, J.M.; Christopher, J.M. Tetrahedron, 2008, 64, 874-882.
(b) Navid, S.; Somayeh, B.; Manije, D. Synthesis, 2008, 13, 2055-2064.
[27]
Xiao-Dong, J.; Yu-Xia, D.; Cai-Xia, Y.; Li, Y.; Zhong-Li, L. Tetrahedron Lett., 2008, 49, 1786-1789.
[28]
(a) Mingos, D.M.P.; Whittaker, A.G.; Van Eldik, R.; Hubbard, C.D. Ed.; John Wiley & Sons: New York,, 1997, pp. 479-514.
(b) Ravichandran, S.; Karthikeyan, E. Chemtech, 2011, 3, 466-470.
[29]
Gabriel, C.; Gabriel, S.; Grant, E.H.; Halstead, B.S.J.; Mingos, D.M.P. Chem. Soc. Rev.,1998, 27, 213-223. (b) Savjani, K.J.; Savjani, T.K.; Patel, S.B.; Gajjar, K.A. Der Pharma Chemica,2010, 2, 342-353. (c) Gawande, M.B.; Shelke, S.N.; Zboril, R.; Varma, R.S. Acc. Chem. Res., 2014, 47, 1338-1348.
[30]
(a) Kappe, C.O.; Doris, D. Nat. Rev. Drug Discov., 2006, 5, 51-63.
(b) Belouezzane, C.; Angelo, C.P.; Antônio, L.S.L.; Fabio, S.M. ChemInform, 2008, 35, 134-218.
[31]
(a) Marta, P.; Lucas, D.D.; Liliana, D.; Gilberto, L.B.A.; Mário, J.F.C.; Mariette, M.P. Inorg. Chim. Acta, 2017, 455, 364-377.
(b) Hernández, J.G. Beilstein J. Org. Chem., 2017, 13, 2372-2373.
[32]
Leticia, J.M.; Maria, L.V.; Alicia, S.C.; Rodolfo, D.B. Lett. Org. Chem., 2017, 14, 8-13.
[33]
Qing, H.L.; Yong, D.; Gang, Z.; Zhen, Z.; Song, M. Curr. Org. Syn., 2017, 14, 462-476.
[34]
Takeshi, K.; Hideyasu, C.; Yutaka, O. Curr. Micro. Chem., 2018, 5, 32-38.
[35]
Asmaa, M.F. Curr. Micro. Chem., 2018, 5, 4-12.
[36]
Haruyasu, A.; Yuki, K.; Pengyu, W.; Kazuya, K.; Nagatoshi, N. Curr. Microw. Chem., 2014, 1, 142-147.
[37]
Liu, B.; Wang, X.; Yang, B.; Xiaohui, W.; Sun, R. Curr. Nanosci., 2011, 7, 1034-1041.
[38]
Majid, M.H.; Setareh, M. Curr. Org. Chem., 2013, 17, 504-527.
[39]
(a) Prakash, T.P.; Perunninakulath, S.P.; Debasish, B.; Sanghamitra, M.; Banik, B.K. Curr. Microw. Chem., 2017, 4, 238-241.
(b) Debasish, B.; Stephanie, M.; Banik, B.K. Molecules, 2012, 17, 2643-2662.
(c) Bandyopadhyay, D.; Banik, B.K. Org. Med. Chem. Lett., 2012, 2, 15-18.
(d) Bandyopadhyay, D.; Banik, B.K. Helv. Chim. Acta, 2010, 93, 298-301.
(e) Bandyopadhyay, D.; Sanghamitra, M.; Rodriguez, R.R.; Banik, B.K. Molecules, 2010, 15, 4207-4212.
[40]
(a) Mordant, C.; Andrade, C.; Touati, R.; Ratovelomanana-Vidal, V.; Hassine, B.B.; Genêt, G.P. Synthesis, 2003, 15, 2405-2409.
(b) Touati, R.; Ratovelomanana-Vidal, V.; Hassine, B.B.; Genêt, J.P. Tetrahedron Asymmetry, 2006, 17, 3400-3405.
(c) Mordant, C.; Reymond, S.; Tone, H.; Lavergne, D.; Touati, R.; Hassine, B.B.; Ratovelomanana-Vidal, V.; Genêt, J.P. Tetrahedron, 2007, 63, 6115-6123.
(d) Prévost, S.; Gauthier, S.; Andrade, M.C.; Mordant, C.; Touati, R.; Lesot, P.; Savignac, P.; Ayad, T.; Phansavath, P.; Vidal, V.; Genêt, J.P. Tetrahedron Asymmetry, 2010, 21, 1436-1446.
(e) Perez, M.; Echeverria, P.G.; Martinez-Arripe, E.; Zoubir, M.E.; Touati, R.; Zhang, Z.; Genêt, J.P.; Phansavath, P.; Ayad, T.; Ratovelomanana-Vidal, V. Eur. J. Org. Chem., 2015, 27, 5949-5958.

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