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Fructose was used as an efficient catalyst for three-component condensation reactions of aryl alde-hydes, malononitrile, and dimedone in a mixture of EtOH and H2O as green solvents. The advantages of this method are a short reaction time, high yields, low cost, easy accesses, and simple work-up. The mechanism of the synthesis of a derivative of 4H-tetrahydrobenzo[b]pyran was clarified using spectroscopic kinetic methods. The activation energy (Ea = 65.34 kJ/mol) and related kinetic pa-rameters (ΔG? = 69.14 kJ/mol, ΔS? = 20.99 J/(mol·K), and ΔH? = 62.89 kJ/mol) were calculated, based on the effects of temperature, concentration, and solvent. The first step in the proposed mechanism was identified as the rate-determining step (k1), based on the steady-state approxima-tion.

参考文献

[1] Alvey L;Prado S;Huteau V;Saint-Joanis B Michel S Koch M Cole S T Tillequin F Janin Y L .[J].Bioorganic and Medicinal Chemistry Letters,2008,16:8264.
[2] Symeonidis T;Chamilos M;Hadjipavlou-Litina DJ;Kallitsakis M;Litinas KE .Synthesis of hydroxycoumarins and hydroxybenzo(f)- or (h)coumarins as lipid peroxidation inhibitors.[J].Bioorganic and Medicinal Chemistry Letters,2009(4):1139-1142.
[3] Narender T;Shweta;Gupta S .[J].Bioorganic and Medicinal Chemistry Letters,2004,14:3913.
[4] Lakshmi V;Pandey K;Kapil A;Singh N;Samant M;Dube A .In vitro and in vivo leishmanicidal activity of Dysoxylum binectariferum and its fractions against Leishmania donovani.[J].Phytomedicine: international journal of phytotherapy and phytopharmacology,2007(1):36-42.
[5] Kumar D;Reddy VB;Sharad S .A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes.[J].European Journal of Medicinal Chemistry,2009(9):3805-3809.
[6] El-Agrody A M;El-Hakim M H;El-Latif M S A;Fakery A H El-Sayed E S M El-Ghareab K A .[J].Acta Pharm,2000,50:111.
[7] Konkoy C S;Fick D B;Cai S X;Lan N C Keana J F W .[J].Chemical Abstracts,2001,134a:29313.
[8] Niknam K;Borazjani N;Rashidian R;Jamali A .[J].催化学报,2013,34:2245.
[9] Devi I;Bhuyan P J .[J].Tetrahedron Letters,2004,45:8625.
[10] Tu S J;Jiang H;Zhung Q Y;Miu C B Shi D Q Wang X S Gao Y .[J].Chinese Journal of Inorganic Chemistry,2003,23:488.
[11] Jin T S;Wang A Q;Shi F;Han L S,Liu L B,Li T S.[J].ARKIVOC,2006:78.
[12] Balalaie S;Shiekh-Ahmadi M;Bararjanian M .[J].CATALYSIS COMMUNICATIONS,2007,8:1724.
[13] Abdolmohammadi S;Balalaie S .[J].Tetrohedron Lett,2007,48:3299.
[14] Gao S;Tsai C H;Tseng C;Yao C F .[J].Tetrahedron,2008,64:9143.
[15] Seifi M;Sheibani H .[J].Catalysis Letters,2008,126:275.
[16] Hekmatshoar R;Majedi S;Bakhtiari K .[J].CATALYSIS COMMUNICATIONS,2008,9:307.
[17] Ren Y M;Cai C .[J].CATALYSIS COMMUNICATIONS,2008,9:1017.
[18] Heravi M M;Jani B A;Derikvand F;Bamoharram F F Oskooie H A .[J].CATALYSIS COMMUNICATIONS,2008,10:272.
[19] Khurana J M;Kumar S .[J].Tetrahedron Letters,2009,50:4125.
[20] Sabitha G;Arundhathi K;Sudhakar K;Sastry BS;Yadav JS .Cerium(III) Chloride-Catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]pyrans[J].Synthetic Communications,2009(3):433-442.
[21] Sun W B;Zhang P;Fan J;Chen S H Zhang Z H .[J].Synthetic Communications,2010,40:587.
[22] Wang L M;Shao J H;Tian H;Wang Y H Liu B .[J].Journal of Fluorine Chemistry,2006,127:97.
[23] Khodaei, M.M.;Bahrami, K.;Farrokhi, A. .Amberlite IRA-400 (OH-) as a catalyst in the preparation of 4h-benzo[b]pyrans in aqueous media[J].Synthetic Communications,2010(10/12):1492-1499.
[24] Fang, D;Zhang, HB;Liu, ZL .Synthesis of 4H-Benzopyrans Catalyzed by Acyclic Acidic Ionic Liquids tin Aqueous Media[J].Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry,2010(1):63-67.
[25] Li Y C;Chen H;Shi C L;Shi D Q Ji S J .[J].Journal of Combinatorial Chemistry,2010,12:231.
[26] Katkar S S;Lande M K;Arbad B R;Gaikwad S T .[J].Chinese Journal of Chemistry,2011,29:199.
[27] Zheng J;Li Y Q .[J].Scholar Research Library,2011,3:381.
[28] Salvi P P;Mandhare A M;Sartape A S;Pawar D K Han S H Kolekar S S .[J].COMPTES RENDUS CHIMIE,2011,14:878.
[29] Karami B;Kiani M;Ahmad Hoseini M .[J].催化学报,2014,35:1206.
[30] Wei J W;Guo W G;Zhang B Y;Liu Y Li C .[J].催化学报,2014,35:1008.
[31] Hazeri N;Maghsoodlou M T;Mir F;Kangani M Saravani H Mol-lashahi E .[J].催化学报,2014,35:391.
[32] Kangani M;Hazeri N;Maghsoodlou M;Salahi S.[J].Research on Chemical Intermediates,2013
[33] Mousavi M R;Hazeri N;Maghsoodlou M T;Salahi S Habi-bi-Khorassani S M .[J].Chinese Chemical Letters,2013,24:411.
[34] Noorisadeh F;Maghsoodlou M T;Hazeri N;Kangani M.[J].Research on Chemical Intermediates,2014
[35] Habibi-Khorassani S M;Ebrahimi A;Maghsoodlou M T;Asheri O Shahraki M Akbarzadeh N Ghalandarzehi Y .[J].International Journal of Chemical Kinetics,2013,45:596.
[36] Habibi-Khorassani S M;Maghsoodlou M T;Ebrahimi A;Farahani F V Mosaddeg E Kazemain M A .[J].Tetrahedron Letters,2009,50:3621.
[37] Habibi-Khorassani S M;Ebrahimi A;Maghsoodlou M T;Zakari-anezhad M Ghasempour H Ghahghayi Z .[J].CURRENT ORGANIC CHEMISTRY,2011,15:942.
[38] Dehdab M;Habibi-Khorassani S M;Shahraki M .[J].Catalysis Letters,2014,144:1790.
[39] Jin TS;Wang AQ;Wang X;Zhang JS;Li TS .A clean one-pot synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by hexadecyltrimethyl ammonium bromide in aqueous media[J].Synlett,2004(5):871-873.
[40] Gurumurthi S;Sundari V;Valliappan R .[J].E-J Chem,2009,6:S466.
[41] Schwartz L M;Gelb R I .[J].Analytical Chemistry,1978,50:1592.
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