- Previous Article
- Next Article
- Table of Contents
Journal of Industrial and Engineering Chemistry, Vol.14, No.3, 401-405, May, 2008
A microwave-assisted synthesis of 3,4-dihydro-pyrimidin-2-(1H)-ones catalyzed by FeCl3-supported Nanopore Silica under solvent-free conditions
E-mail:,
Lewis acid supported Nanopore Silica catalysts for microwave-assisted Biginelli reaction under solvent-free conditions were prepared by impregnating FeCl3 dissolved in ethanol to Nanopore Silica at 40 degrees C. Biginelli reaction under solvent-free conditions, one-pot three-component condensation of urea, benzaldehyde, and ethyl acetoacetate, catalyzed with porous material or Lewis acid supported porous material, such as MCM-41, SBA-15, VSB-5, Nanopore Silica, FeCl3/MCM-41, FeCl3/Nanopore Silica, CeCl3/Nanopore Silica and InCl3/Nanopore Silica, was investigated. Our recent results of the microwave-assisted Biginell reaction of some benzaldehyde derivatives starting materials using MCM-41, Nanopore Silica, FeCl3/Nanopore Silica, under solvent-free conditions are also reported. Aromatic aldehydes carrying either electron releasing or electron withdrawing substituents in the ortho, meta, and para positions afforded good yields of the products using MCM-41 as a catalyst. When Nanopore Silica was used as a catalyst, the yield of the Biginelli product was in the range of 27-56%. However FeCl3/Nanopore Silica has been employed as a catalyst, the yield of the Biginelli product was increased dramatically. Thus it has been found that the use of FeCl3/Nanopore Silica as heterogeneous catalyst has made this method very cost effective. (C) 2008 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.
Keywords:FeCl3-supported Nanopore Silica;Biginelli reaction;microwave-assisted;solvent-free conditions;heterogeneous catalyst
- Kappe CO, Accounts Chem. Res., 33, 879 (2000)
- Atwal KS, Swanson BN, Unger SE, Floyd DM, Moreland S, Hedberg A, O’Reilly BC, J. Med. Chem., 34, 806 (1991)
- Rovnyak GC, Atwal KS, Hedberg A, Kimball SD, Moreland S, Gougoutas SJZ, O’Reilly BC, Schwartz J, Malley MF, J. Med. Chem., 35, 3254 (1992)
- Barrow JC, Nantermet PG, Selnick HG, Glass KL, Rittle KE, Gilbert KF, Steele TG, Homnick CF, Freindeger RM, Ransom RL, O’Malley SS, Olah TV, Ellis JD, Barrish A, Kassahun K, Leppert P, Nagarathnam D, Forray C, J. Med. Chem., 43, 2703 (2000)
- Kappe CO, Shishkin OV, Uray G, Verdino P, Tetrahedron, 56, 1859 (2000)
- Biginelli P, Gazz. Chim. Ital., 23, 360 (1893)
- Kappe CO, Tetrahedron, 49, 6937 (1993)
- Kappe CO, Stadler A, Org. React., 63, 1 (2004)
- Zhu J, Bienayme H, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005, , For reviews on multicomponent reactions, see also
- Ugi I, Domling A, Horl W, Endeavour, 18, 115 (1984)
- Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating T, Accounts Chem. Res., 29, 123 (1996)
- Tietze LF, Lieb ME, Curr. Opin. Chem. Biol., 2, 363 (1998)
- Domling A, Comb. Chem. High Throughput Screening, 1, 1 (1998)
- Dax SL, McNally JJ, Youngman MA, Curr. Med. Chem., 6, 255 (1999)
- Tietze LF, Modi A, Med. Res. Rev, 20, 304 (2000)
- Bienayme H, Hulme C, Oddon G, Schmitt P, Chem. Eur. J., 6, 3321 (2000)
- Ugi I, Heck S, Comb. Chem. High Throughput Screening, 4, 1 (2001)
- Domling A, Curr. Opin. Chem. Biol., 6, 306 (2002)
- Corma A, Garcia H, Chem. Rev., 103, 4307 (2003)
- Juaristi E, Munoz-Muniz O, ARKIVOC XI, 16 (2003)
- Lu J, Bai Y, Wang Z, Yang B, Ma H, Tetrahedron Lett., 41, 9075 (2000)
- Rannu BC, Hajra A, Jana U, J. Org. Chem., 65, 6270 (2000)
- Chari MA, Syamasundar K, J. Mol. Catal. A-Chem., 221, 137 (2004)
- Salehi P, Zolfigol MA, Shirini F, Baghbanzadeh M, Curr. Org. Chem., 10, 2171 (2006)
- Augustine RL, Heterogeneous Catalysis for the Synthetic Chemist, Marcel Dekker, New York (1996)
- Chang W, Ahn BJ, Int. J. Nanotechnol., 2006(2), 186 (2006)
- Han CS, Lee HY, Roh Y, Int. J. Nanotechnol., 2006(2), 236 (2006)
- Hayes BL, Microwace Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews (2002)
- Bogdal D, Microwave-assisted Organic Synthesis, Elsvier, Amsterdam (2005)
- Loupy A, Microwave in Organic Synthesis, Wiley-VCH, Weinheim (2002)
- Kappe CO, Stadler A, Microwaves in Organic and Medicinal Chemistry, Wiley-VCH, Weinheim (2005)
- Tanaka K, Solvent-free Organic Synthesis, Wiley-VCH,Weinheim (2003)
- Chang W, Shin J, Kim M, Ahn BJ, J. Ind. Eng. Chem., 7(1), 62 (2001)
- Chang W, Shin J, Song JE, Ahn BJ, J. Korean Ind. Eng. Chem., 15(1), 146 (2004)
- Ku HJ, Ahn BJ, Jeon BE, Chang W, J. Ind. Eng. Chem., 11(6), 841 (2005)
- Doxsee KM, Hutchinson JE, Green Organic Chemistry, Brooks Cole, Singapore (2004)
- Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS, Nature, 359, 710 (1990)
- Sujandi, Prasetyanto EA, Han SC, Park SE, Bull. Korean Chem. Soc., 27, 1381 (2006)
- Jhung SH, Yoon JW, Hwang JS, Cheetham AK, Chang JS, Chem. Mater., 17, 4455 (2005)
- Han CS, Lee HY, Chon H, Proc. Ann. Meeting Nano Sci. Tech., 185 (2004)
- Han CS, Lee HY, Kim MH, Mo HR, Lim MO, Kim JH, Lim EJ, Jung DY, Proc. Ann. Meeting Nano Sci. Tech., 151 (2004)
- Chang W, Shin J, Oh Y, Ahn BJ, J. Ind. Eng. Chem., 14 (2008)
- Park SH, Kim BH, Selvaraj M, Lee TG, J. Ind. Eng. Chem., 13(4), 637 (2007)
- Chon H, Chon MJ, Han CS, Korean Patent 0396457 (2003)
- Multimode microwave batch reactor from CEM (Mars-5) was employed for microwave-assisted reactions at 400 W. This instrument features a built-in magnetic stirrer, direct temperature control of the reaction mixture with the aid of a shielded thermocouple, and software that enables online temperature/pressure control by regulation of microwave power output. This microwave reactor can be equipped with a sealed PFA vessel for carrying out reactions at elevated temperature