超声辐射下肟及肟醚的合成
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摘要
本文综述了近年来醛酮与盐酸羟胺缩合生成肟的各种方法,以及肟在有机反应诸如脱肟、肟的醚化、脱水、贝克曼重排等反应中的一些应用。着重研究了超声辐射下醛或酮与盐酸羟胺在乙醇或水中缩合生成肟的反应以及利用超声辐射与相转移催化剂苄基十四烷二甲基氯化铵的结合由肟进行醚化生成肟醚的反应。
醛或酮与盐酸羟胺在超声辐射下于乙醇中缩合可得到较好收率的肟；在水溶液经超声辐射无需催化剂于室温反应可得到72%-98%收率的肟。
超声辐射下在苄基十四烷二甲基氯化铵存在下,肟与二氯甲烷、氢氧化钠反应可得较高收率的亚甲基二肟醚；由肟和苄基溴反应可得到68%-96%的肟醚。
与传统方法相比,该方法具有操作简便,反应时间短,产率高等优点。
Some new methods for the reaction of aldehydes or ketones with hydroxylamine hydrochloride resulting oximes and the application of oximes in some organic reactions in the recent years were reviewed in this paper. The condensation of aldehydes and ketones with hydroxylamine hydrochloride results oximes in good yields in EtOH or water under ultrasound irradiation. The etherification of oximes to give oxime ethers catalyzed by combination of benzyldimethyltetradecylammonium chloride and ultrasonication was also studied.
The condensation of aldehydes and ketones with hydroxylamine hydrochloride results oximes in good yields in EtOH under ultrasound irradiation; and the condensation in water without catalyst afforded oximes in 72%-98% yields in water under ultrasound irradiation.
The reaction of oximes with dichloromethane in the presence of sodium hydroxide by combination of benzyldimethyltetradecylammonium chloride and ultrasonication afforded the corresponding methylene dioximes in excellent yields; the reaction of aldoximes with benzyl bromide in water afforded the corresponding oxime ethers in 68%-96% yields in the same condition.
Compared with conventional methods, the advantages in the present procedure are easier workup, shorter reaction time and higher yields.
醛或酮与盐酸羟胺在超声辐射下于乙醇中缩合可得到较好收率的肟；在水溶液经超声辐射无需催化剂于室温反应可得到72%-98%收率的肟。
超声辐射下在苄基十四烷二甲基氯化铵存在下,肟与二氯甲烷、氢氧化钠反应可得较高收率的亚甲基二肟醚；由肟和苄基溴反应可得到68%-96%的肟醚。
与传统方法相比,该方法具有操作简便,反应时间短,产率高等优点。
Some new methods for the reaction of aldehydes or ketones with hydroxylamine hydrochloride resulting oximes and the application of oximes in some organic reactions in the recent years were reviewed in this paper. The condensation of aldehydes and ketones with hydroxylamine hydrochloride results oximes in good yields in EtOH or water under ultrasound irradiation. The etherification of oximes to give oxime ethers catalyzed by combination of benzyldimethyltetradecylammonium chloride and ultrasonication was also studied.
The condensation of aldehydes and ketones with hydroxylamine hydrochloride results oximes in good yields in EtOH under ultrasound irradiation; and the condensation in water without catalyst afforded oximes in 72%-98% yields in water under ultrasound irradiation.
The reaction of oximes with dichloromethane in the presence of sodium hydroxide by combination of benzyldimethyltetradecylammonium chloride and ultrasonication afforded the corresponding methylene dioximes in excellent yields; the reaction of aldoximes with benzyl bromide in water afforded the corresponding oxime ethers in 68%-96% yields in the same condition.
Compared with conventional methods, the advantages in the present procedure are easier workup, shorter reaction time and higher yields.
引文
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[3]Arisawa, M.; Yamaguchi, M. Rhodium-catalyzed beckmann rearrangement, Org. Lett.,2001,3, 311-312; (b) Luca, L. D.; Giacomelli, G.; Porcheddu, A. beckmann rearrangement of oximes under very mild conditions, J. Org. Chem.,2002,67,6272-6274.
[4]Bandgar, B. P.; Nikat, S. M.; Wadgaonkar, P. P. The reduction of aromatic oximes to amines with borohydride exchange resin-nickel acetate system, Synth. Commun.,1995,25,863-869.
[5]Hosseini Sarvari, M., ZnO/CH3COCl:a new and highly efficient catalyst for dehydration of aldoximes into niriles under solvent-free condition, Synthesis,2005,5,787-790.
[6]Shedge, A. S.; Kavitake, B. P.; Desai, U. V.; Wadgaonkar, P. P. A simple method for synthesis of methylene dioximes using poly (ethylene glycol)-400 as a phase transfer catalyst, Synth. Commun., 2004,34,4483-4486.
[7]Ley, J. P.; Bertram, H. J. Hydroxy-or methoxy-substituted benzaldoximes and benzaldehyde-O-alkyloximes as tyrosinase inhibitors, Bioorganic & Medicinal Chemistry,2001,9,1879-1885.
[8]Shen, C.; Sigman, D.S. New inhibitors of aldose reductase:anti-oximes of aromatic aldehydes, Arch. Biochem. Biophys.,1991,286,596-603.
[9]宋宝安,刘新华,杨松,胡德禹,金林红,张玉涛；肟类衍生物的合成与农药生物活性的研究进展.有机化学,2005,25(5),507-525.
[10]Otsuka Pharmaceutical Co. Ltd., Jpn. Kokai Tokkyo Koho JP 81,108,757 (1981); "Dioximate compounds" Chem. Abstr.,1982,96,34870 f.
[11]李在国；有机中间体制备,第二版,化工出版社,北京,2002,p.315.
[12]Campbell, K. N.; Mckenna, J. F. The action of Grignard reagents on oximes.1. The action of phenylmagnesium bromide on mixed ketoximes, J. Org. Chem.,1939,4,198-205.
[13]Hosokava, T.; Ohta, T.; Okamoto, Y.; Murahashi, S.-I. Alkylation of ketoximes with dichloromethane using bases under phase-transfer conditions. Formation of methylene dioximes and novel heteromacrocyclic compounds. Bull. Chem. Soc. Jpn.1985,58,194-200.
[14]Kirsch, S. J.; Schelling, H. Methylene dioxime formation using phase transfer catalysis, J. Org. Chem., 1979,44,3970-3972.
[15]Kukushkin, V. Y.; Pombeiro, A. J. L. Oxime and oximate metal complexes:unconventional synthesis and reactivity, Coordination Chemistry Reviews,1999,181,147-175.
[16]Dayagi, S.; Degani, Y. in:Patai, S. (Ed.), The Chemitstry of Carbon-Nitrogen Double Bond, interscience, London,1970, p.61.
[17]Sharghi, H.; Hosseini Sarvari, M. Selective synthesis of E and Z isomers of oximes, Synlett,2001,1, 99-101.
[18]Sharghi, H.; Hosseini Sarvari, M. Sovent-free and one-step Beckmann rearrangement of ketones and aldehydes by zinc oxide, Synthesis,2002,8,1057-1060.
[19]Chen,Y. X.; Li, J. T.; Li, X. L.; Deng, H. J. An efficient procedure for synthesis of oximes by grinding, Asian Journal of Chemistry,2007,19 (3),2236-2240.
[20]Hajipour, A. R.; Mallakpour, S. E.; Imanzadeh, G. A rapid and convenient synthesis of oximes in dry media under microwave irradiation, J. Chem. Research,1999,228-229.
[21]Li, J. T.; Li, X. L.; Li, T. S. Synthesis of oximes under ultrasound irradiation, Ultrason. Sonochem., 2006,13,200-202.
[22]Li, X. L.; Li, J. T. Ultrasound promoted synthesis of ketoximes, C. J. I.,2006,8(9),57.
[23]李记太,李晓亮,李同双；超声辐射下水溶液中芳醛肟的合成,有机化学,2006,26(11),1594-1596.
[24]Bhar, S.; Guha, S. Highly selective regeneration of carbonyl compound from their oximes and semicarbazones in aqueous medium, Synth. Commun.,2005,35,1183-1188.
[25]Boruah, A.; Baruah, B.; Prajapati, D.; Sandhu, J. S. Regeneration of carbonyl compounds from oximes under microwave irradiations, Tetrahedron Lett.,1997,38(24),4267-4268.
[26]Chavan, S. P.; Soni, P. A facile deprotection of oximes using glyoxylic acid in an aqueous medium, Tetrahedron Lett.,2004,45,3161-3162.
[27]史达清,赵红,王香善,屠树江；低价钛引起的芳酮肟的反应,有机化学,2004,24(2),216-218.
[28]Yadav, J. S.; Sasmal, P. K.; Chand, P. K. Iodine as a new deoximating agent, Synth. Commun.,1999, 29(21),3667-3671.
[29]Shinada, T.; Yoshihara, K. A facile method for the coversation of oximes to ketones and aldehydes by the use of activated MnO2, Tetrahedron Lett.,1995,36(37),6701-6704.
[30]Li, Z.; Ding, R. B.; Xing, Y. L.; Shi, S. Y. Solvent-free rapid deprotection of ketone and aldehyde oximes using periodic acid, Synth. Commun.,2005,35,2515-2520.
[31]Ali, M. H.; Green, S.; Wiggin, C. J.; Khan, S. Oxidative cleavage of oximes with silica-gel-supported chromic acid in nonaqueous media, Synth. Commun.,2006,35,1761-1767.
[32]Lakouraj, M. M.; Noorian., M.; Mokhtary, M. Amberlyst 15 supported nitrosonium ion as an efficientreagent for regeneration of carbonyl compounds from oximes,hydrazones and semicarbazones, Reactive & Functional Polymers,2006,66,910-915.
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