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Hexamolybdate/BTEAC composite catalyzed condensation reaction for the synthesis of xanthenedione derivatives research[J]. Journal of South China Normal University (Natural Science Edition), 2017, 49(4): 34-38.
Citation: Hexamolybdate/BTEAC composite catalyzed condensation reaction for the synthesis of xanthenedione derivatives research[J]. Journal of South China Normal University (Natural Science Edition), 2017, 49(4): 34-38.

Hexamolybdate/BTEAC composite catalyzed condensation reaction for the synthesis of xanthenedione derivatives research

Funds: 

The National Natural Science Foundation of China

More Information
  • Received Date: October 29, 2015
  • Revised Date: November 27, 2015
  • A series of xanthenedione derivatives have been efficiently synthesized from condensation reaction between aromatic aldehydes and 1,3-cyclohexanedione or 5,5-dimethyl-1,3-cyclohexane dione which co-catalyzed by hexamolybdate and benzyl triethyl ammonium chloride (BTEAC). In addition, the reaction solvent, composite catalyst and composite catalyst dosage have been studied. The catalytic system can be easily seperated and reused up to four times without loss of catalytic activities. All synthetic compounds have been identified and characterized by means of melting point, IR, 1H NMR, 13C NMR, MS and X-ray diffraction analysis, and the possible reaction mechanism has been proposed.
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    [1]Muharrem K, Erhan B, Ferdag C.Synthesis and antimicrobial activity of some bisoctahydroxanthene-1,8-dione derivatives[J].Med Chem Res, 2011, 20(8):1214-1219
    [2]Poupelin J P, Saint-Ruf G, Foussard-Blanpin G O, Narcisse G, Uchida-Ernouf G, Lacroix R.Synthesis and antiinflammatory properties of bis(2-hydroxy-1-naphthyl)methane derivativesIMonosubstituted derivatives[J].Eur J Med Chem, 1978, 13(1):67-71
    [3]Lu Z Y, Lin Z J, Wang W L, Du L, Zhu T J, Fang Y C, et al.Citrinin dimers from the halotolerant fungus Penicillium citrinum B-57[J].J Nat Prod., 2008, 71(4):543-546
    [4]Carroll A R, Lamb J, Moni R, Guymer G P, Forster P I, Quinn R J.Myrtucommulones FeI phloroglucinols with thyrotropin-releasing hormone receptor-2 binding af?nity from the seeds of corymbia scabrida[J].J Nat Prod, 2008, 71(4):1564-1568
    [5]Zhang Y, Wang M G, Liang J, Shang Z C.J].Lett[J].Org. Chem., 2010, 7(1):27-27
    [6]N Mulakayala, P V N S Murthy, D Rambabu, M Aeluri, R Adepu, G R Krishna, C M Reddy, K R S Prasad, M Chaitanya, C S Kumar, M V B Rao, M Pal.[J].Bioorg Med Chem Lett, 2012, 22(6):2186-2191
    [7]宋永彬, 刘波.新型氧杂蒽和呋喃衍生物的合成及其抗肿瘤活性研究[D]. 黑龙江: 哈尔滨工业大学, 2013.
    [8]Song Yongbing, Liu Bo.The study of the synthesis and the anti-humor activity of new xanthene and furan derivatives [D]. Hei Longjiang: Harbin Institute Of Technology, 2013.
    [9]赵新海, 李燕萍, 刘晨江.嘧啶酮和氧杂蒽化合物的合成研究[D]. 新疆: 新疆大学, 2010.
    [10]Zhao XinHai, Li YanPing, Liu ChenJiang.The study of the synthesis of pyrimidinone and xanthene [D]. Xin Jiang:Xin Jiang University, 2010.
    [11]A M El-Brashy, M El-Sayed Metwally, F A El-Sepai.Spectrophotometric determination of some ?uoroquinolone antibacterials by binary complex formation with xanthene dyes[J][J].IL Farmaco, 2004, 59(10):809-817
    [12]Silvia G, Angela R, Alessandra B, et al.Synthesis and antitumor activity of new derivatives of xanthen- 9-one- 4- acetic acid[J].J Med Chem, 2002, 45(22):4931-4939
    [13]Sheldon R A.Atom Efficiency and Catalysis in Organic Synthesis[J].Pure Appl Chem, 2000, 72(7):1233-1246
    [14]K Chibale, M R Visser, D V.Schalkwyk,P J Smith,A Saravanamuthu,A H FairlambExploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents[J].J].Tetrahedron, 2003, 59(13):2289-2296
    [15]Brooks G T, Ottridge A P, Mace D W.The Effect of Some Furochromene and Benzochromene Analogues of 2,2-dimethyl-7-methoxychromene (precocene I) and Benzofuran Precursors on Oncopeltus Fasciatus (dallas) and Locusta Migratoria Migratorioides (R&F)[J].Pesticide Science, 1998, 22(1):41-41
    [16]Ion R M.The photodynamic therapy of cancer—a photosensitization or a photocatalytic process[J].Prog. Catalysis, 1997, 2(1):55-76
    [17]Ruf G S, De A, Hieu H T.[J].Bulletin of Chimica Therapeutics, 1972, 7(1):83-83
    [18]Tetsuo N, Yasuteru, Takatoshi Y.Preparation of xanthene derivative for photodynamic therapy: PCT Int Appl WO, 2007072800[P]. 2007-06-28.
    [19]aHilderbrand S A, Weissleder R.One-Pot Synthesis of New Symmetric and Asymmetric Xanthene Dyes[J].Tetrahedron Lett, 2007, 48(25):4383-4385
    [20]B B Bhowmik, P Ganguly.Photophysics of xanthene dyes in surfactant solution[J].Spectrochim Acta, 2005, 61(1):1997-2003
    [21]Akio O, Ippei T, Takahiro K, Hiroshi N, Itaru H.Turn-on fluorescence sensing of nucleoside polyphosphates using a xanthene-based Zn (Ⅱ) complex chemosensor[J].J Am Chem Soc, 2008, 130(36):12095-12101
    [22]M Ahmad, T A King, D K Ko, B H Cha, J Lee.Performance and photostability of xanthene and pyrromethene laser dyes in sol–gel phases[J].Phys D Appl Phys, 2002, 35(1):1473-1476
    [23]Janet C, Erhan D, Francisco M.Photochromic compounds for fluorescence nanoscopy[J].Curr Phys Chem, 2011, 1(3):232-241
    [24]Sato N, Jitsuoka M, Shibata T, Hirohashi T, Nonoshita K, Moriya M, Haga Y, Sakuraba A, Ando M, Ohe T, Iwaasa H, Gomori A, Ishihara A, Kanatani A, Fukami T.S)-9-(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one,a selective and orally active neuropeptide Y Y5 receptor antagonist[J].J Med Chem, 2008, 51(15):4765-4770
    [25]Verma G K, Raghuvanshi K, Vervia R K, et al.An efficient one- pot solvent-free synthesis and photophysical properties of 9-arylalkyl-octahydroxanthene-1,8-diones[J].Tetrahedron, 2011, 67(20):3698-3704
    [26]SHUKLA Q VERMA R K, VERMA G K, et al.Solvent-Free Sonochemical One-Pot Three-Component Synthesis of 2H-Indazolo[2,1-b]Phthalazine-1,6,11-Triones and 1 H-Pyrazolo[1,2-b]Phthalazine- 5,10-Diones[J].Tetrahedron Lett, 2011, 52(52):7195-7198
    [27]Liang Bo, KALIDINDI S, PORCO J A, et al.Multicomponent Reaction Discovery: Three-Component Synthesis of Spirooxindoles[J].Org Lett, 2010, 12(3):572-575
    [28]R Z Wang, L F Zhang, Z S Cui.Iodine-catalyzed synthesis of 12-aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one derivatives via multi-component reaction[J].Synth. Commun, 2009, 39(1):2101-2107
    [29]A Zarei, A R Hajipour, L Khazdooz.The one-pot synthesis of 14-arylalkyl-14H-dibenzo[a,j]xanthenes catalyzed by P2O5Al2O3 under microwave irradiation[J].Dyes Pigments, 2010, 85(1):133-138
    [30]Dabiri M, Baghbanzadeh M, Nikcheh MS, Arzroomchilar E.Eco-friendly and effcient one-pot synthesis of alkyl-or aryl-14H-dibenzo[a,j]xanthenes in water[J].Bioorg Med Chem Lett, 2008, 18(1):436-438
    [31]Das B, Thirupathi P, Ravinder Reddy K, Ravikanth B, Nagarapu L.J].Catal[J].Commun, 2007, 8(1):535-538
    [32]Zhang Z H, Liu Y H.Antimony trichlorideSiO2 promoted synthesis of 9-ary-3,4,5,6,7,9-hexahydroxanthene-1,8-diones[J].Catal Commun, 2008, 9(1):1715-1719
    [33]张美月, 刘敏, 李越敏.无相转移剂水相中, , , -四甲基- -芳基-, , , , , , , -八氢化氧杂蒽-, -二酮的合成[J].化学试剂, 2009, 31(12):1026-1028
    [34]Zhang Meiyue, Liu Min, Li Yuemin.The synthesis of 3,3,6,6-tetramethyl-9-aryl-1,2,3,4,5,6,7,8-octahydroindolo xanthene-1,8-dione in the aqueous without phase transfer agents[J].Journal of chemical reagents, 2009, 31(12):1026-1028
    [35]Safaei Ghomi J, Ghasemzadeh M A.Zinc oxide nanoparticles: a highly ef?cientand readily recycylable catalyst for the synthesis of xanthenes[J].Chin Chem Lett, 2012, 23(1):1225-1229
    [36]Mirjalili B F, Bamoniri A, Akbari A, Taghavinia N.Nano-TiO2: An eco-friendly and re-usable catalyst for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes[J].Iran Chem Soc, 2011, 8(1):129-134
    [37]Kumar Dhruva, Sandhu J S.Efficient,Solvent-Free,Microwave-Enhanced Condensation of 5,5-Dimethyl-l,3-Cyclohexanedione with Aldehydes and Imines Using Libr as Inexpensive,Mild Catalyst[J].Synthetic Commun, 2010, 40(4):510-517
    [38]Karthikeyan G, Pandurangan A.Heteropoly acid (H3PW12O40) supported MCM-41:An efficient solid acid catalyst for the green synthesis of xanthenedione derivatives[J].J Mol Catal A Chem, 2009, 311(1-2):36-45
    [39]MULAKAYALA N, PAVAN KUMAR G, RAMBABU D, et al.A Greener Synthesis of 1,8-Dioxo-Octahydroxanthene Derivatives under Ultrasound[J].Tetrahedron Lett, 2012, 53(51):6923-6926
    [40]ZARE A, MOOSAVI-ZARE A R, MERAJODDIN M, et al.Ionic Liquid Triethylamine-Bonded Sulfonic Acid [(Et3N-SO3H)Cl] as A Novel,Highly Efficient and Homogeneous Catalyst for The Synthesis of B-Acetamido Ketones 1,8-Dioxo-Octahydroxanthenes and 14-Ary 1-14H-Dibenzo[a,j] Xanthenes[J].J Mol Liq, 2012, 167(1):69-77
    [41]范学森, 李艳贞, 张新迎, 等.离子液体介质中?催化下芳香醛与, -二甲基-, -环己二酮的缩合反应[J].有机化学, 2005, 25(11):1482-1486
    [42]Fang Xuesen, Li Yanzhen, Zhang Xinying, et al.Ionic Liquids under FeCl3?6H2O catalyzed aromatic aldehydes and 5,5-dimethyl-1,3-cyclohexanedione condensation reaction[J].Chinese Journal of Organic Chemistry, 2005, 25(11):1482-1486
    [43]Hua G P, Li T J, Zhu S L, et al.[J].J Org Chem, 2005, 25(6):716-719
    [44]Jin T S, Qi N, Li M, Han L S, Liu L B, Li T S.J].Asian Chem[J].Asian Chem, 2007, 19(1):3803-3809
    [45]Das B, Thirupathi P, Mahender I, Reddy V S, Rao Y K.Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines[J].J Mol Catal A Chem., 2006, 247(1):233-239
    [46]Shakibaei G I, Mirzaei P, Bazgir A.Dowex50W promoted synthesis of 14-aryl-14 H-dibenzo[ a,j]xanthene and 1,8-dioxo-octahydroxanthene derivatives under solvent-free conditions[J].Appl Catal A Gen, 2007, 325(1):188-192
    [47]Jin T S, Zhang J S, Wang A Q, et al.Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry[J].Synth Commun, 2005, 35(17):2339-2345
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