摘要
肟是一类重要的有机中间体,可以用来制备胺、酰胺、噁唑(异噁唑)、吡啶、硝酮、腈、肟醚等化合物。本文按照反应类型,综述了近几年来肟在有机反应诸如脱肟、还原、脱水、贝克曼重排和醚化等反应中的应用进展。
主要研究了以蒙脱土K10固载氯铬酸铵为氧化剂在二氯甲烷中氧化酮肟、超声辐射下一锅法由肟合成芳甲基乙酰胺和以氨基磺酸与氯化锌共催化酮肟在乙腈中的Beckmann重排。与文献报道的方法相比,后处理操作简单、反应时间缩短、反应产率提高。
Oxime is a very important synthetic intermediate for the preparation of amines, amides, oxazoles (isoxazoles), pyridine, nitrones, nitriles and oxime-ethers. In this thesis, some applications of oxime in the organic synthesis were reviewed in recent years according to kinds of the organic reactions.
Oxidative deoximation of ketoxime with ammonium chlorochromate (ACC)/montmorillonite K10 in dichloromethane, one-pot synthesis of benzylacetamide from oxime under ultrasound irradiation and the Beckmann rearrangement of ketoxime catalyzed by sulfamic acid and zinc chloride in acetonitrile were studied. Compared to the reported methods, the main advantage of the present procedure is simple work-up procedure, shorter reaction time and higher yield.
引文
[1](a) Demir, A. S. A novel synthesis of optically active a-amino acids [J]. Pure & Appl. Chem.,1997, 69:105-108. (b) Tandon, V. K.; Kumar, M.; Awasthi, A. K. et al. Potential hypotensive agents: synthesis and hypotensive activity of oxime ethers derived from 1-naphthoxepines and related compounds [J]. Bioorg. Med. Chem. Lett.,2004,14:3177-3180.
[2](a) Bandgar, B. P.; Nikat, S. M.; Wadgaonkar, P. P. The reduction of aromatic oximes to amines with borohydride exchange resin-nickel acetate system [J]. Synth. Commun.,1995,25:863-869. (b) Abiraj, K.; Gowda, D. C. Zinc/ammonium formate:a new facile system for the rapid and selective reduction of oximes to amines [J]. J. Chem. Res.,2003,332-334.
[3](a) Furuya, Y.; Ishihara, K.; Yamamoto, H. Cyanuric chloride as a mild and active Beckmann rearrangement catalyst [J]. J. Am. Chem. Soc.,2005,127:11240-11241. (b) Zhu, M.; Cha, C. T.; Deng, W. P. et al. A mild and efficient catalyst for the Beckmann rearrangement, BOP-Cl [J]. Tetrahedron Lett.,2006,47:4861-4863.
[4](a) Peter, W.; Joan, M. F.; Laura, S. Microwave promoted oxazole synthesis:cyclocondensation cascade of oximes and acyl chlorides [J]. Tetrahedron Lett.,2005,46:5463-5466. (b) Kurangi, R. F.; Kawthankar, R.; Sawal, S. et al. Convenient synthesis of 3,5-disubstituted isoxazoles [J]. Synth. Commun.,2007,37:585-587.
[5](a) Chibiryaev, A. M.; Kimpe, N. D.; Tkachev, A. V. Michael addition of ethyl acetoacetate to a, (3-unsaturated oximes in the presence of FeCl3:a novel synthetic route to substituted nicotinic acid derivatives [J]. Tetrahedron Lett.,2000,41:8011-8013. (b) Saikia, P.; Prajapati, D.; Sandhu, J. S. A novel indium-catalysed synthesis of tetra-substituted pyridine derivatives [J]. Tetrahedron Lett.,2003, 44:8725-8727.
[6]Nakama, K.; Sekia, S.; Kanemasa, S. A new synthetic access to N-alkylated nitrones through Lewis acid-catalyzed conjugate additions of aldoximes [J]. Tetrahedron Lett.,2001,42:6719-6722.
[7](a) Boruah, M.; Konwar, D. AlCl3.6H2O/KI/H2O/CH3CN:a new alternate system for dehydration of oximes and amides in hydrated media [J]. J. Org. Chem.,2002,67:7138-7139. (b) Anand, N.; Owston, N. A.; Parker, A. J. et al. Ruthenium-catalysed conversion of oxime ethers into nitriles [J]. Tetrahedron Lett.,2007,48:7761-7763.
[8](a) Bertelsen, S.; Diner, P.; Johansen, R. L. et al. Asymmetric organocatalytic β-hydroxylation of a, P-unsaturated aldehydes [J]. J. Am. Chem. Soc.,2007,129:1536-1537. (b) Jia, X. D.; Da, Y. X.; Yang, C. X. et al. O-alkylation of oxime with N-vinyl lactams induced by radical cation [J]. Tetrahedron Lett.,2008,49:1786-1789. (c) Li, J. T.; Li, X. L. An efficient and practical synthesis of methylene dioximes by combination of ultrasound and phase transfer catalyst [J]. Ultrason. Sonochem.,2007,14:677-679.
[9](a)张建余,赵金垣.肟类对急性有机磷中毒解毒机制的研究进展[J].中华劳动卫生职业病杂志,1998,16：371-373.(b)王汉斌,关里,李万华,等.肟类化合物对有机磷农药抑制红细胞乙酰胆碱酯酶功能的研究[J].中华内科杂志,2005,44：454-455.(c)宋宝安,刘新华,杨松,等.肟类衍生物的合成与农药生物活性的研究进展[J].有机化学,2005,25：507-525.
[10](a) Barry, R. H.; Hartung, W. H. α-Oximino acids intermediates for the synthesis a-amino acids [J]. J. Org. Chem.,1947,12:460-468. (b) Barton, D. H. R.; Beaton, J. M.; Geller, L. E. et al. A new photochemical reaction [J]. J. Am. Chem. Soc.,1961,83:4076-4083.
[11]Kukushkin, V. Y.; Pombeiro, A. J. L. Oxime and oximate metal complexes:unconventional synthesis and reactivity [J]. Coord. Chem. Rev.1999,181:147-175.
[12](a)王海侠,胡宗超,徐静.甲醛肟法测定配合物中锰的含量[J].贵州科学,2006,24：24-27.(b)高玉敏,刘冰.丁二肪光度法测定粗镍中的镍[J].铁合金,2007,37-40.(c)石太宏,肖云,王卓超,丁二酮肟/氯仿体系萃取分离铂、钯[J].环境科学学报,2008,28：120-124.
[13]Mikhaleva, A. I.; Zaitsev, A. B.; Trofimov, B. A. Oximes as reagents [J]. Russ. Chem. Rev.,2006, 75:797-823.
[14]Garnovskii, D. A.; Kukushkin, V. Y. Metal-mediated reactions of oximes [J]. Russ. Chem. Rev., 2006,75:111-124.
[15]Brooks, S. G.; Evans, R. M.; Green, G. F. H. et al.930. Use of 20-oximes and 20-semicarbazones in making cortisol and 4:5a-dihydrocortisol [J]. J. Chem. Soc.,1958,4614-4628.
[16]赵文超,沙耀武.脱肟方法的综述[J].有机化学,1996,16：121-132.
[17]Shirini, F.; Zolfigol, M. A.; Mallakpour, B. et al. A mild and efficient method for cleavage of C=N using Mg(HSO4)2 in the presence of wet SiO2 [J]. Tetrahedron Lett.,2002,43:1555-1556.
[18]Shirini, F.; Zolfigol, M. A.; Safari, A. et al. Regeneration of carbonyl compounds by cleavage of C=N bonds under mild and completely heterogeneous conditions [J]. Tetrahedron Lett.,2003,44: 7463-7465.
[19]De, S. K. SiBr4/wet silica as an efficient heterogeneous system for cleave of C=N [J]. Tetrahedron Lett.,2003,44:9055-9056.
[20]Martin, M.; Martinez, G.; Urpi, F. et al. Conversion of ketoximes to ketones trimethylphosphine and 2,20-dipyridyl diselenide [J]. Tetrahedron Lett.,2004,45:5559-5561.
[21]Chavan, S. P.; Soni, P. A facile deprotection of oximes using glyoxylic acid in an aqueous medium [J]. Tetrahedron Lett.,2004,45:3161-3162.
[22]Bose, D. S.; Reddy, A. V. N.; Das, A. P. R. Simple, economical and environmental benign selective regeneration of carbonyl compounds from oximes and N, N-dimethyl Hydrazones [J]. Synthesis-Stuttgart,2003,1883-1885.
[23]Bhar, S.; Guha, S. Highly selective regeneration of carbonyl compound from their oximes and semicarbazones in aqueous medium [J]. Synth. Commun.,2005,35:1183-1188.
[24]Gogoi, P.; Hazarika, P.; Konwar, D. Surfactant/I2/water:an efficient system for deprotection of oximes and imines to carbonyls under neutral conditions in water [J]. J. Org. Chem.,2005,70: 1934-1936.
[25]Balicki, R.; Kaczmarek, L. Mild reductive deoximation with TiCl4/NaI reagent system [J]. Synth. Commun.,1991,21:1777-1782.
[26]Mukai, C.; Nomura, I.; Kataoka, O. et al. Dicocaltoctacarbonyl-mediated deoximation [J]. Synthesis, 1999,1872-1874.
[27]Das, N. B.; Nanda, B.; Nayak, A. SnCl2-SiO2:A selective reagent for efficient regeneration of carbonyls from nitrogenous derivatives [J]. Synth. Commun.,2002,32:3647-3651.
[28]Arnold, J. N.; Hayes, P. D.; Kohaus, R. L. et al. Bismuth compounds in organic synthesis. Deprotection of ketoximes using bismuth bromide-bismuth triflate [J]. Tetrahedron Lett.,2003,44: 9173-9175.
[29]Shinada, T.; Yoshihara, K. A facile method for the coversation of oximes to ketones and aldehydes by the use of activated MnO2 [J]. Tetrahedron Lett.,1995,36:6701-6704.
[30]Chrisman, W.; BlankinshiP, M. J.; Taylor, B. et al. Selective deoximation using alumina supported potassium permanganate [J]. Tetrahedron Lett.,2001,42:4775-4777.
[31]Imanzadeh, G. H.; Hajipour, A. R.; Mallakpour, S. E. Solid state cleavage of oximes with potassium permanganate supported on alumina [J]. Synth. Commun.,2003,33:735-740.
[32]Hashemi, M. M.; Akhbari, M.; Karimi-Jaberi, Z. Solid phase regeneration of carbonyl compounds by oxidative cleavage of carbon-nitrogen double bonds with molecular oxygen at room temperature [J]. Lett. Org. Chem.,2006,3:121-122.
[33]Salehi, P.; Khodaei, M. M.; Goodarzi, M. A mild and selective deoximation method using y-picolinium chlorochromate (y-PCC) [J]. Synth. Commun.,2002,32:1259-1263.
[34]Ganguly, N. C.; Sukai, A. K.; De, S. et al. Oxidative deprotection of oximes using pyridinum fluorochromate and hydrogen peroxide [J]. Synth. Commun.,2001,31:1607-1612.
[35]Pourali, A. R.; Goli, A. Efficient conversion of oximes to the corresponding carbonyl compounds with tetrabutylammonium chromate under aprotic conditions [J]. Bull. Korean Chem. Soc.,2006,27: 587-588.
[36]Ali, M. H.; Green, S.; Wiggin, C. J. et al. Oxidative cleavage of oximes with silica-gel-supported chromic acid in nonaqueous media [J]. Synth. Commun.,2006,36:1761-1767.
[37]Zhang, G. S.; Yang, D. H.; Chen, M. F. et al. Oxidative deoximation to their parent carbonyl compounds with ammonium chlorochromate adsorbed on alumina [J]. Synth. Commun.,1998,28: 2221-2225.
[38]Li, J. T.; Meng, X. T. Deoximation of Ketoximes to Ketones with Ammonium Chlorochromate/Montmorillonite K10 in Dichloromethane [J]. E-J. Chem.,2009,6:156-160.
[39]Firouzabadi, H.; Iranpoor, N.; Amani, K. Activation of iron(III) and bismuth(III) nitrates by tungstophosphoric acid:Solvent-free oxidative deprotection of oximes to carbonyl compounds [J]. Synth. Commun.,2004,34:3587-3593.
[40]Karami, B.; Montazerozohori,M.; Karimipour, G. R. et al. Tungstate sulfuric acid (TSA)/NaNO2 as a novel heterogeneous system for rapid deoximation [J]. Bull. Korean Chem. Soc.2005,26: 1431-1433.
[41]Hajipour, A. R.; Zahmatkesh, S.; Ruoho, A. E. Methyl triphenylphosphonium peroxydisulfate (MTPPP):A mild and inexpensive reagent for the cleavage of oximes, phenylhydrazones and 2,4-dinitrophenylhydrazones to the corresponding carbonyl compounds under non-aqueous conditions [J]. J. Iran. Chem. Soc.,2008,5:54-58.
[42]Jain, N.; Kumar, A.; Chauhan, S. M. S. Metalloporphyrin and heteropoly acid catalyzed oxidation of C=NOH bonds in an ionic liquid:biomimetic models of nitric oxide synthase [J]. Tetrahedron Lett., 2005,46:2599-2602.
[43]Ballistreri, F. P.; Chiacchio, U.; Rescifina, A. et al. Conversion of oximes to carbonyl compounds by triscetylpyridinium tetrakis(oxodiperoxotungsto) phosphate(PCWP)-mediated oxidation with hydrogen peroxide [J]. Molecules,2008,13:1230-1237.
[44]Li, Z.; Ding, R. B.; Xing, Y. L. et al. Solvent-free rapid deprotection of ketone and aldehyde oximes using periodic acid [J]. Synth. Commun.,2005,35:2515-2520.
[45]Khazaei, A.; Manesh, A. A. Facile regeneration of carbonyl compounds from oximes under microwave irradiations using N-bromophthalimide [J]. J. Braz. Chem. Soc.,2005,16:874-876.
[46]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 [J]. React. Funct. Polym.,2006,66:910-915.
[47]Adharvana Chari, M.; Shobha, D.; Kiran Kumar, T. et al. Polymer (PVP) supported ferric chloride as a heterogeneous catalyst for selective deprotection of aldoximes and hydrazone [J]. Trends Appl. Sci. Res.,2007,2:28-32.
[48]Deshpande, S. S.; Sonavane, S. U.; Jayaram, R. V. A facile deprotection of oximes over mixed metal oxides under solvent-free conditions [J]. Catal. Commu.,2008,9:639-644.
[49]Li, D. M.; Shi, F.; Guo, S. et al. One-pot synthesis of silica gel confined functional ionic liquid: effective catalysts for deoximation under mild condition [J]. Tetrahedron Lett.,2004,45:265-268.
[50]Zhou, W.; Li, Q. H; Peng, S. An efficient solid state method for deoximation under mild conditions [J]. Chin. Chem. Lett.,2006,17:1559-1562.
[51]尤启东,周后元,王其灼,等.催化氢转移还原肟成胺[J].中国医药工业杂志,1991,22：316-318.
[52]Rogers, R. S.; Stern, M. K. An improved synthesis of the phosphonic acid analog of tryptophan [J]. Synlett.,1992,78-78.
[53]Abiraj, K.; Gowda, D. C. Magnesium-catalyzed reduction of oximes to amines using ammonium formate [J]. Synth. Commun.,2004,34:599-605.
[54]胡名扬,席尚忠,沈文斌,等.低价钛引起肟的还原偶联反应[J].南京大学学报,1992,28：88-91.
[55]史达清,周龙虎,高原,等.低价钛引起的芳香醛肟的还原偶联反应[J].化学通报,1997,41-43.
[56]史达清,赵红,王香善,等.低价钛引起的芳酮肟的反应[J].有机化学,2004,24：216-218.
[57]Kise, N.; Ueda, N. Reductive coupling of aromatic oxims and azines to 1,2-diamines using Zn-MsOH or Zn-TiCl4[J]. Tetrahedron Lett.,2001,42:2365-2368.
[58]Laso, N. M.; Quiclet-Sire, B.; Zard, S. Z. A new selective reduction of nitroalkenes into enamides[J]. Tetrahedron Lett.,1996,37:1605-1608.
[59]Burk, M. J.; Casy, G.; Johnson, N. B. A three-step procedure for asymmetric catalytic reductive amidation of ketones [J]. J. Org. Chem.1998,63:6084-6085.
[60]Allwein, S. P.; Christopher McWilliams, J.; Secord, E. A. et al. Efficient synthesis of chiral phenethylamines:preparation, asymmetric hydrogenation, and mild deprotection of ene-trifluoroacetamides [J]. Tetrahedron Lett.,2006,47:6409-6412.
[61]刘永波,江国防,郭灿城.由肟一锅法合成乙酰苄胺衍生物[J].化学试剂,2008,30：57-58.
[62]赵文超.醛肟脱水试剂[J].化学试剂,1997,19：273-280.
[63]Iranpoor, N.; Zeynizadeh, B. Efficient dehydration of aldoximes to nitriles with TiCl3(OTf) [J]. Synth. Commun.,1999,29:2747-2752.
[64]Kato, Y.; Ooi, R.; Asano, Y. A new enzymatic method of nitrile synthesis by Rhodococcus sp. strain YH3-3 [J]. J. Mol. Catal. B:Enzym.,1999,6:249-256.
[65]Yang, S. H.; Chang, S. Higly efficient and catalytic conversion of aldoximes to nitriles [J]. Org. Lett., 2001,3:4209-4211.
[66]Dewan, S. K.; Singh, R. Synthesis of nitriles from aldoximes using silica gel as catalyst under microwave irradiation [J]. Synth. Commun.,2003,33:3085-3088.
[67]Lee, K.; Han, S. B.; Yoo, E. M. et al. Efficient transformation of aldoximes to nitriles using 2-chloro-1-methylpyridium iodide under mild conditions [J]. Synth. Commun.,2004,34: 1775-1782.
[68]Hosseini Sarvari, M. ZnO/CH3COCl:a new and highly efficient catalyst for dehydration of aldoximes into niriles under solvent-free condition [J]. Synthesis,2005,787-790.
[69]Oskooie, H. A.; Heravi, M. M.; Jaddi, Z. One-pot conversion of aldoximes into nitriles via aldoxime tosylates under microwave irradiation [J]. Phosphorus, Sulfur, and Silicon,2005,180:1993-1996.
[70]Bandgar, B. P.; Makone, S. S. Organic reaction in water:Transformation of aldehydes to nitriles using NBS under mild condition [J]. Synth. Commun.,2006,36:1347-1352.
[71]Furuya, Y.; Ishihara, K.; Yamamoto, H. Perrhenic acid catalyzed dehydration from primary amides, aldoximes, N-monoacylureas, and a-substituted ketoximes to nitrile compounds [J]. Bull. Chem. Soc. Jpn.,2007,80:400-406.
[72]Zuidema, D. R.; Dennison, A. L.; Park, E. Y. et al. Conversion of aldoximes into nitriles with Raney nickel in refluxing 2-propanol [J]. Synth. Commun.,2008,38:3810-3815.
[73]Kokare, N. D.; Shinde, D. B. Efficient conversion of aldoximes to nitriles using phosphoric acid diethyl ester 2-phenylbenzimidazol-l-yl ester [J]. Monatsh. Chem.,2009,140:185-188.
[74]Dewan, S. K.; Singh, R.; Kumar, A. One pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride using sodium sulphate (anhyd) and sodium bicarbonate in dry media under microwave irradiation [J]. ARKIVOC,2006,41-44.
[75]Movassagh, B.; Fazeli, A. Direct synthesis of aromatic nitriles from aldehydes using hydroxylamine and oxalyl chloride [J]. Synth. Commun.,2007,37:623-628.
[76]李德江,孙碧海,李斌.浅谈Beckmann重排反应在有机合成中的应用[J].化学教育,2004,25：7-9.
[77]Chandrasekhar, S.; Gopalaiah, K. Beckmann rearrangement of ketoximes on solid metaboric acid:a simple and effective procedure [J]. Tetrahedron Lett.,2002,43:2455-2457.
[78]Luca, L. D.; Giacomelli, G. Porcheddu, A. Beckmann rearrangement of oximes under very mild conditions [J]. J. Org. Chem.2002,67:6272-6274.
[79]Chandrasekhar, S.; Gopalaiah, K. Beckmann reaction of oximes catalysed by chloral:mild and neutral procedures [J]. Tetrahedron Lett.,2003,44:755-756.
[80]Wang, B.; Gu, Y. L.; Luo, C. et al. Sulfamic acid as a cost-effective and recyclable catalyst for liquid Beckmann rearrangement, a green process to produce amides from ketoximes without waste [J]. Tetrahedron Lett.,2004,45:3369-3372.
[81]Li, D. M.; Shi, F.; Guo, S. et al. Highly efficient Beckmann rearrangement and dehydration of oximes [J]. Tetrahedron Lett.,2005,46:671-674.
[82]Sardarian, A. R.; Shahsavari-Fard, Z.; Shahsavari, H. R. et al. Efficient Beckmann rearrangement and dehydration of oximesvia phosphonate intermediates [J]. Tetrahedron Lett.,2007,48: 2639-2643.
[83]Xiao, L. F.; Xia, C. G.; Chen, J. p-Toluenesulfonic acid mediated zinc chloride:highly effective catalyst for the Beckmann rearrangement [J]. Tetrahedron Lett.,2007,48:7218-7221.
[84]Moghaddam, E. M.; Rad, A. A. R.; Zali-Boinee, H. Solid supported microwav-assisted Beckmann rearrangement of ketoximes in dry Media [J]. Synth. Commun.,2004,34:2071-2075.
[85]Dongare, M. K.; Bhagwat, V. V.; Ramana, C. V. et al. Silica supported MoO3:a mild heterogeneous catalyst for the Beckmann rearrangement and its application to some sugar derived ketoximes [J]. Tetrahedron Lett.,2004,45:4759-4762.
[86]Xiao, L. F.; Peng, J. J.; Xia, C. G. A novel method for Beckmann rearrangement of oximes with silica sulfuric acid under mild condition [J]. Chin. Chem. Lett.,2006,17:617-620.
[87]Li, Z.; Ding, R. B.; Lu, Z. et al. Silica sulfate as a recyclable and efficient catalyst for Beckmann rearrangement under microwave irradiation [J]. J. Mol. Catal. A:Chem.,2006,250:100-103.
[88]Eshghi, H.; Hassankhani, A. One-pot efficient Beckmann rearrangement of ketones catalyzed by silica sulfuric acid [J]. J. Korean Chem. Soc.,2007,51:361-364.
[89]Peng, J. J.; Deng, Y. Q. Catalytic Beckmann rearrangement of ketoximes in ionic liquids [J]. Tetrahedron Lett.,2001,42:403-405.
[90]Ren, R. X.; Zueva, L. D.; Ou, W. Formation of ε-caprolactam via catalytic Beckmann rearrangement using P2O5 in ionic liquids [J]. Tetrahedron Lett.,2001,42:8441-8443.
[91]Guo, S.; Deng, Y. Q. Environmentally friendly Beckmann rearrangement of oximes catalyzed by metaboric acid in ionic liquids [J]. Catal. Commun.,2005,6:225-228.
[92]Gui, J. Z.; Deng, Y. Q.; Hua, Z. D. et al. A novel task-specific ionic liquid for Beckmann rearrangement:a simple and effective way for product separation [J]. Tetrahedron Lett.,2004,45: 2681-2683.
[93]Elango, K.; Srirambalaji, R.; Anantharaman, G. Synthesis of N-alkylimidazolium salts and their utility as solvents in the Beckmann rearrangement [J]. Tetrahedron Lett.,2007,48:9059-9062.
[94]王洪林,张文媛.在负载离子液体的MCM-48上的环己酮肟重排[J].云南大学学报(自然科学版),2008,30：180-186.
[95]Sharghi, H.; Sarvari, M. H. One-step Beckmann rearrangement from carbonyl compounds and hydroxylamine hydrochloride in Al2O3/CH3SO3H (AMA) as a new reagent [J]. J. Chem. Res.,2001, 446-449.
[96]Sharghi, H.; Hosseini Sarvari, M. Sovent-free and one-step Beckmann rearrangement of ketones and aldehydes by zinc oxide [J]. Synthesis,2002,1057-1060.
[97]Chandrasekhar, S.; Gopalaiah, K. Ketones to amides via a formal Beckmann rearrangement in'one pot':a solvent-free reaction promoted by anhydrous oxalic acid. Possible analogy with the Schmidt reaction [J]. Tetrahedron Lett.,2003,44:7437-7439.
[98]Gopalakrishnan, M.; Sureshkumar, P.; Kanagarajan, V. et al. A simplified green chemistry approaches to organic synthesis in solid media. Activated fly ash, an industrial waste (pollutant) as an efficient and novel catalyst for some selected organic reactions in solvent-free conditions under microwave irradiation [J]. ARKIVOC,2006,130-141.
[99]柳爱平,刘兴平,陈灿,等.肟醚类衍生物的合成及生物活性研究[J].华中师范大学学报(自然科学版),2004,38：66-68.
[100]王胜得,杨春明,刘兴平,等.基于苯乙酮的肟醚-酰胺类化合物的合成及生物活性研究[J].湖南师范大学自然科学学报,2005,28：56-59.
[101]Shedge, A. S.; Kavitake, B. P.; Desai, U. V. et al. A simple method for synthesis of methylene dioximes using poly (ethylene glycol)-400 as a phase transfer catalyst [J]. Synth. Commun.,2004, 34:4483-4486.
[102]De, P.; Nonappa; Pandurangan, K. et al. CuI-mediated cross-coupling of aryl halides with oximes:A direct access to O-aryloximes [J]. Org. Lett.,2007,9:2767-2770.
[103](a) Li, J. T.; Li, X. L.; Li, T. S. Synthesis of oximes under ultrasound irradiation [J]. Ultrason Sonochem.,2006,13:200-202. (b)李记太,李晓亮,李同双.超声辐射下水溶液中芳醛肟的合 成[J].有机化学,2006,26：1594-1596.
[104]Katsura, Y.; Tomishi, T.; Inoue, Y. et al. Anti-helicobacter pylori agents.4.2-(Substituted guanidino)-4-phenylthiazoles and some structurally rigid derivatives [J]. J. Med. Chem.,2000,43: 3315-3321.
[105]Beutler, J. A.; Chmurny, G. N.; Clark, P. et al. Two novel phenolics from actinomadura verrucosospora [J]. J. Antibiot.,1990,43:107-109.
[106]Shi, M.; Cui, S. C. Transamidation catalyzed by a recoverable and reusable polyDMAP-based Hafnium Chloride and montmorillonite KSF [J]. Synth. Commun.,2005,35:2847-2858.
[107](a) Li, J. T.; Wang, S. X.; Chen, G. F. et al. Some applications of ultrasound irradiation in organic synthesis [J]. Curr. Org. Synth.,2005,2:415-436. (b) Li, J. T.; Yang, W. Z.; Wang, S. X. et al. Improved synthesis of chalcones under ultrasound irradiation [J]. Ultrason. Sonchem.,2002,9: 237-239.
[108]Carothers, W. H.; Bickford, C. F.; Hurwitz, G. J. The preparation and base strengths of some amines [J]. J. Am. Chem. Soc.,1927,49:2908-2914.
[109]Carothers, W. H.; Jones, G. A. The preparation of some primary amines by the catalytic reduction of nitriles [J]. J. Am. Chem. Soc.,1925,47:3051-3057.
[110]Ritter, J. J.; Minieri, P. P. A new reaction of nitriles. I. amides from alkenes and mononitriles [J]. J. Am. Chem. Soc.,1948,70:4045-4048.
[111]Ruben, A. A.; Roberto, A. R. SRN1 mechanism in bifunctional systerm [J]. J. Org. Chem.,1980,45: 4760-4763.
[112](a) Wang, B.; Yang, L. M.; Suo, J. S. Ionic liquid-regulated sulfamic acid:chemoselective catalyst for the transesterification of β-ketoesters [J]. Tetrahedron Lett.,2003,44:5037-5039. (b) Wang, B.; Yang, L. M.; Suo, J. S. Solvent-Free Tetrahydropyranylation of alcohols with sulfamic acid as reusable catalyst [J]. Synth. Commun.,2003,33:3929-3934.
[113](a) Du, G.; Zhang, Q. The Beckmann rearrangement of acetophenonoxime under ultrasonic irradiation [J]. J. Hebei Univ. (Nat. Sci. Ed.),1997,38-40. (b) Zhou, H.; Huang, W. Beckmann rearrangement of benzophenoneoxime under ultrasonic irradiation [J]. J. An Qing Teach. Coll. (Nat. Sci.),2002,8:42-45.
[114]Kullertz, G.; Fischer, G.; Barth, A. Sekundare D-isotopieeffekte bei der hydrolyse von p-nititroacetanilid [J]. Tetrahedron,1976,32:759-761.
[115]Newman, M. S.; Hung, W. M. An improved aromatization of α-tetralone oximes to N-(1-naphthyl)acetamides [J]. J. Org. Chem.,1973,38:4073-4074.
[116]Nicanor, G.; Marcial, M. M.; Sebastian, R. M. et al. Dimethoxyethane as an alternative solvent for Schmidt reactions. Preparation of homochiral N-(5-oxazolyl)oxazolidinones from N-acetoacetyl derivatives of oxazolidinones [J]. Tetrahedron,1996,52:1609-1616.
[117]Thakur, A. J.; Boruah, A.; Prajapati, D. et al. Microwave induced bismuth trichloride catalysed Beckmann rearrangement of oximes [J]. Synth. Commun.,2000,30:2105-2111.