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Journal of Zhejiang University SCIENCE B 2008 Vol.9 No.12 P.990-995

http://doi.org/10.1631/jzus.B0820079


L-Proline as an efficient and reusable promoter for the synthesis of coumarins in ionic liquid


Author(s):  Xiu-hong LIU, Ji-cai FAN, Yang LIU, Zhi-cai SHANG

Affiliation(s):  Department of Chemistry, Zhejiang University, Hangzhou 310027, China

Corresponding email(s):   shangzc@zju.edu.cn

Key Words:  L-Proline, Ionic liquid, Coumarins, Knoevenagel condensation


Xiu-hong LIU, Ji-cai FAN, Yang LIU, Zhi-cai SHANG. L-Proline as an efficient and reusable promoter for the synthesis of coumarins in ionic liquid[J]. Journal of Zhejiang University Science B, 2008, 9(12): 990-995.

@article{title="L-Proline as an efficient and reusable promoter for the synthesis of coumarins in ionic liquid",
author="Xiu-hong LIU, Ji-cai FAN, Yang LIU, Zhi-cai SHANG",
journal="Journal of Zhejiang University Science B",
volume="9",
number="12",
pages="990-995",
year="2008",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.B0820079"
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%0 Journal Article
%T L-Proline as an efficient and reusable promoter for the synthesis of coumarins in ionic liquid
%A Xiu-hong LIU
%A Ji-cai FAN
%A Yang LIU
%A Zhi-cai SHANG
%J Journal of Zhejiang University SCIENCE B
%V 9
%N 12
%P 990-995
%@ 1673-1581
%D 2008
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.B0820079

TY - JOUR
T1 - L-Proline as an efficient and reusable promoter for the synthesis of coumarins in ionic liquid
A1 - Xiu-hong LIU
A1 - Ji-cai FAN
A1 - Yang LIU
A1 - Zhi-cai SHANG
J0 - Journal of Zhejiang University Science B
VL - 9
IS - 12
SP - 990
EP - 995
%@ 1673-1581
Y1 - 2008
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.B0820079


Abstract: 
The effect of l-Proline as a promoter on the condensation reaction of salicylaldehyde or its derivatives with ethyl acetoacetate in neutral ionic liquid [emim]BF4 was studied. All reactions were carried out under mild reaction conditions and achieved high yields. Moreover, the ionic liquid containing l-Proline could be recycled and reused for several times without noticeably decreasing in productivity. The results show that the l-Proline-[emim]BF4 system has a potential in contribution to the development of environmentally friendly and inexpensive processes in organic syntheses.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

[1] Bigi, F., Chesini, L., Maggi, R., Sartori, G., 1999. Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids. J. Org. Chem., 64(3):1033-1035.

[2] Bogdal, D., 1998. Coumarins: fast synthesis by Knoevenagel condensation under microwave irradiation. J. Chem. Res. Synop., 998(8):468-469.

[3] Camur, M., Bulut, M., 2008. The synthesis and characterization of novel soluble phthalocyanines substituted with 7-octyloxy-3-(4-oxyphenyl) coumarin moieties. Dyes and Pigments, 77(1):165-170.

[4] Cartwright, G.A., McNab, H., 1997. Synthesis of coumarins by flash vacuum pyrolysis of 3-(2-hydroxyaryl)propenoic esters. J. Chem. Res. Synop., 1997(8):296-297.

[5] Chen, Y.L., Lu, C.M., Lee, S.J., Kuo, D.H., Chen, I.L., Wang, T.C., Tzeng, C.C., 2005. Synthesis, antiproliferative, and vasorelaxing evaluations of coumarin α-methylene-γ-butyrolactones. Bioorganic & Medicinal Chemistry, 13(20):5710-5716.

[6] Chowdari, N.S., Ramchary, D.B., Barbas, C.F., 2003. Organocatalysis in ionic liquids: highly efficient L-proline-catalyzed direct asymmetric Mannich reactions involving ketone and aldehyde nucleophiles. Synlett, (12):1906-1909.

[7] Córdova, A., 2004. Direct catalytic asymmetric cross-aldol reactions in ionic liquid media. Tetrahedron Lett., 45(20):3949-3952.

[8] Czerney, P., Hartmann, H., 1982. A simple route to N-(2-hydroxyarylidene)nitroanilines, versatile synthons for coumarins. Journal für Praktische Chemie., 324(1):21-28 (in German).

[9] Fang, D., Cheng, J., Gong, K., Shi, Q.R., Liu, Z.L., 2008. Synthesis of coumarins via pechmann reaction in water catalyzed by acyclic acidic ionic liquids. Catal. Lett., 121(3-4):255-259.

[10] Fry, J.R., Hammond, A.H., Jassi, K.L., Bass, A.E., Bruce, G., Laughton, C., Shaw, P.N., Bylov, I.E., Kovalenko, S.M., 2004. Selectivity of 7-alkoxycoumarins as probe substrates for rat hepatic cytochrome P450 forms is influenced by the substitution pattern on the coumarin nucleus. Xenobiotica, 34(8):707-722.

[11] Gruttadauria, M., Riela, S., Meo, P.L., D′Anna, F., Noto, R., 2004. Supported ionic liquid asymmetric catalysis. A new method for chiral catalysts recycling. The case of proline-catalyzed aldol reaction. Tetrahedron Lett., 45(32):6113-6116.

[12] Gu, Y.L., Zhang, J., Duan, Z.Y., Deng, Y.Q., 2005. Pechmann reaction in non-chloroaluminate acidic ionic liquids under solvent-free conditions. Adv. Synth. Catal., 347(4):512-516.

[13] Hagiwara, H., Okabe, T., Hoshi, T., Suzuki, T., 2004. Catalytic asymmetric 1,4-conjugate addition of unmodified aldehyde in ionic liquid. J. Mol. Catal. A: Chem., 214(1):167-174.

[14] Hirai, T., Togo, H., 2005. Preparation and synthetic use of polymer-supported Acetoaceacetate Reagent. Synthesis, (16):2664-2668.

[15] Joseph, T., Sahoo, S., Halligudi, S.B., 2005. Brönsted acidic ionic liquids: a green, efficient and reusable catalyst system and reaction medium for Fischer esterification. J. Mol. Catal. A: Chem. 234(1-2):107-110.

[16] Kisanga, P., Fei, X.S., Verkade, J., 2002. P(RNCH2CH2)3N: an efficient promoter for the synthesis of 3-substistuted coumarins. Synth. Commun., 32(8):1135-1144.

[17] Kitazume, T., Jiang, Z.J., Kasai, K., Mihara, Y., Suzuki, M., 2003. Synthesis of fluorinated materials catalyzed by proline or antibody 38C2 in ionic liquid. J. Fluorine Chem., 121(2):205-212.

[18] Kostova, I.N., Nikolov, N.M., Chi Pilska, L.N., 1993. Antimicrobial properties of some hydroxycoumarins and fraxinus ornus bark extracts. J. Ethnopharm., 39(3):205-208.

[19] Kotrusz, P., Kmentova, I., Gotov, B., Toma, S., Solcaniova, E., 2002. Proline-catalysed asymmetric aldol reaction in the room temperature ionic liquid [bmim]PF6. Chem. Commun., 2(21):2510-2511.

[20] Kotrusz, P., Toma, S., Schmalz, H.G., Adler, A., 2004. Michael additions of aldehydes and ketones to β-nitrostyrenes in an ionic liquid. Eur. J. Org. Chem., 2004(7):1577-1583.

[21] Kotrusz, P., Alemayehu, S., Toma, S., Schmalz, H.G., Adler, A., 2005. Enantioselective organocatalysis in ionic liquids: addition of aliphatic aldehydes and ketones to diethyl azodicarboxylate. Eur. J. Org. Chem., 2005(22):4904-4911.

[22] Loh, T.P., Feng, L.C., Yang, H.Y., Yang, J.Y., 2002. L-Proline in an ionic liquid as an efficient and reusable catalyst for direct asymmetric aldol reactions. Tetrahedron Lett., 43(48):8741-8743.

[23] Mitra, A.K., De, A., Ka Rchaudhuri, N., Misra, S.K., Mukhopadhyay, A.K., 1998. Synthesis of coumarins in search of better nonpeptidic HIV protease inhibitors. J. India Chem. Soc., 75(10-12):666-671.

[24] Mogilaiah, K., Reddy, C.S., Reddy, G.R., 2003. Microwave assisted rapid and efficient synthesis of 3-acetylcoumarins. Indian J. Heterocycl. Chem., 12(3):285-286.

[25] Palmer, C.J., Josephs, J.L., 1995. Synthesis of the calophyllum coumarins. J. Chem. Soc. Perkin Trans., 1(24):3135-3152.

[26] Rasalkar, M.S., Potdar, M.K., Mohile, S.S., Salunkhe M.M., 2005. An ionic liquid influenced L-proline catalysed asymmetric Michael addition of ketones to nitrostyrene. J. Mol. Catal. A: Chem., 235(1-2):267-270.

[27] Salaheldin, A.M., Yi, Z., Kitazume, T., 2004. Synthesis of fluoromethylated materials derived from 2-trifluoromethyl acrylic acid phenethyl ester in an ionic liquid. J. Fluorine Chem., 125(7):1105-1110.

[28] vanden Eynde, J.J., Rutot, D., 1999. Microwave-mediated derivatization of poly (styrene-co-allyl alcohol), a key step for the soluble polymer-assisted synthesis of heterocycles. Tetrahedron, 55(9):2687-2694.

[29] Wang, C.J., Hsieh, Y.J., Chu, C.Y., Lin, Y.L., Tseng, T.H., 2002. Inhibition of cell cycle progression in human leukemia HL-60 cells by esculetin. Cancer Lett., 183(2):163-168.

[30] Wang, Y., Shang, Z.C., Wu, T.X., Fan, J.C., Chen, X., 2006. Synthetic and theoretical study on proline-catalyzed Knoevenagel condensation in ionic liquid. J. Mol. Catal. A: Chem., 253(1-2):212-221.

[31] Wang, Z.M., Bao, W.L, Jiang, Y., 2005. L-Proline promoted ullmann-type reaction of vinyl bromides with imidazoles in ionic liquids. Chem. Commun., 5(22):2849-2851.

[32] Watson, B.T., Christiansen, G.E., 1998. Solid phase synthesis of substituted coumarin-3-carboxylic acids via the Knoevenagel condensation. Tetrahedron Lett., 39(33):6087-6090.

[33] Yavari, I., Hekmat, S.R., Zonouzi, A., 1998. A new and effkient route to 6-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt. Tetrahedron Lett., 39(16):2391-2392.

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