Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid

Year 2012, Volume: 25 Issue: 3, 617 - 621, 19.07.2012

Rahim Hekmatshoar , Mojgan Kargar Zahra Hashemı Fereshteh Golı Abdoljalil Mostasharı

Abstract

A highly efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones in 2-ethylhexanoic acid as green, low cost and recoverable catalytic medium, illustrates good synthetic utility of this method.

Keywords

2-ethylhexanoic acid, 3, 4-dihydropyrimidin-2(1H)-ones/thiones, organocatalyst.

References

• Kappe, C.O., “Recent advances in the Biginelli dihydropyrimidine synthesis: new tricks from an old dog,,, Acc. Chem. Res., 33: 879-888 (2000).
• Kappe, C.O., “100 years of the Biginelli dihydropyrimidine synthesis,,, Tetrahedron., 49: 6937-6963 (1993).
• Kappe, C.O., Fabian, W.M.F., Semones, M.A., “Conformational dihydropyrimidine calcium channel modulators A comparison of ab initio, semi-empirical and X-ray crystallographic studies,,, Tetrahedron., 53: 2803- 2816 (1997). of 4-aryl
• Atwal, K.S., Swanson, B.N., Unger, S.E., Floyd, D.M., Moreland, S., Hedberg, A., O’Reilly, B.C., “Dihydropyrimidine Calcium Channel Blockers. 3- Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5- pyrimidinecarboxylic acid esters as orally effective antihypertensive agents,,, J. Med. Chem., 34: 806- 811 (1991).
• Kappe, C.O., Shishkin, O.V., Uraya, G., Verdinoa, P., “X-Ray Structure, conformational analysis, enantioseparation, and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol,,, Tetrahedron., 56: 1859-1862 (2000).
• Heys, L., Moore, C.G., Murphy, P.J., “The guanidine metabolites of Ptilocaulis spiculifer and related compounds; isolation and synthesis,,, Chem. Soc. Rev., 29: 57-67 (2000).
• Biginelli, P., “Derivati aldeiduredici degli eteri acetil-e dossal-acetico,,, Gazz .Chim. Ital., 23: 360- 416 (1893). 8. Banik, B.K., Reddy, A.T., Datta, A., Mukhopadhyay, C., “Microwave-induced bismuth nitrate-catalyzed synthesis of dihydropyrimidones via Biginelli condensation under solventless conditions,,, Tetrahedron Lett., 48: 7392-7394 (2007).
• Li, J.T., Han, J.F., Yang, J.H., Li, T.S., “An efficient 3,4-dihydr- NH2SO3H catalyzed irradiation,,, Ultrason .Sonochem., 10: 119-122 (2003).
• opyrimidin-2-ones under ultrasound
• Debache, A., Amimour, M., Belfaitah, A., Rhouati, S., Carboni, B., “A one-pot Biginelli synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by triphenylphosphine as Lewis base,,, Tetrahedron Lett., 49: 6119-6121 (2008).
• Tu, Sh., Fang, F., Miao, Ch., Jiang, H., Feng, Y., Shi, D., Wang, X., “One-pot synthesis of 3,4- dihydropyrimidin-2(1H)-ones using Boric acid as catalyst,,, Tetrahedron Lett., 44: 6153-6155 (2003).
• Azizian, J., Mohammadi, A.A., Karimi, A.R., Mohammadizadeh, M.R., “KAl(SO4)2.12H2O supported on silica gel as a novel heterogeneous system synthesis of di-hydropyrimidinones under solvent- free conditions,,, Appl. Catal. A. Gen., 300: 85-88 (2006). reaction One-pot
• Su, W., Li, J., Zheng, Zh., Shen, Y., “One-pot synthesis of dihydropyrimi- diones catalyzed by strontium(II) triflate under solvent-free conditions,,, Tetrahedron Lett., 46: 6037-6040 (2005).
• Fu, N.Y., Yuan, Y.F., Pang, M.L., Wang, J.T., Peppe, preparation of ferrocenedihydropyrimidinones,,, J. Organomet. Chem., 672: 52-57 (2003).
• Ming, L., Si, G. W., Rong, W.L., Feng, L.Y., Zheng, Y.H., “One-pot synthesis of Biginelli and Hantzsch products catalyzed by non-toxic ionic liquid (BMImSac) and structural determination of two products,,, J. Mol. Catal. A: Chem., 258: 133- 138 (2006).
• Nandurkar, N.S., Bhanushali, M.J., Bhor, M.D., Bhanage, B.M., “Y (NO3)3.6H2O: A novel and reusable catalyst for one pot synthesis of 3,4- dihydropyrimidin-2(1H)-ones under solvent-free conditions,,, J .Mol. Catal .A. Chem., 271: 14-17 (2007).
• Ghosh, R., Maiti, S., Chakraborty, A., “In(OTf)3- catalysed dihydropyrimidin-2(lH)-ones,,, J. Mol. Catal. A. Chem., 217: 47-50 (2004). of 3,4
• Ahmed, N., Lier, J.E.V., “TaBr5-catalyzed Biginelli reaction: one-pot synthesis of 3,4-dihydropyrimidin- 2-(1H)-ones/thiones under solvent-free conditions ,,, Tetrahedron. Lett., 48: 5407-5409 (2007).
• Adib, M., Ghanbary, K., Mostofi, M., Ganjali, M.R., “Efficient Ce(NO3)·6HO-catalyzed solvent-free synthesis Molecules., 11: 649-654 (2006).
• Karade, H.N., Sathe, M., Kaushik, M.P., “Synthesis of 4-aryl substituted 3, 4-dihydropyrimidinones using silica-chloride under solvent free conditions,,, Molecules., 12: 1341-1351 (2007).
• Pandiarajan, C.K., “Calcium fluoride: an efficient and reusable catalyst for the synthesis of 3,4- dihydropyrimidin-2(1H)-ones corresponding 2(1H)thione: an improved high yielding protocol for the Biginelli reaction,,, Tetrahedron. Lett., 50: 2222-2224 (2009). their using 12
• Paraskar, A.S., Dewkar, G.K., Sudalai, A., “Cu(OTf)2: a reusable catalyst for high-yield synthesis Tetrahedron. Lett., 44: 3305-3308 (2003).
• Asghari, S., Tajbakhsh, M., Kenari, B.J., Khaksar, S., dihydropyrimidine-2(1H)-one/thiones under neat conditions,,, Chin. Chem. Lett., 22: 127-130 (2011).
• Salim, S.D., Akamanchi, K.G., “Sulfated tungstate: An alternative, eco-friendly catalyst for Biginelli reaction,,, Catal. Commun. 12: 1153-1156 (2011).
• Kargar, M., Hekmatshoar, R., Mostashari, A.J., Hashemi, Z., “Efficient and green synthesis of 3,4- dihydropyrimidin-2(1H)-ones/thiones imidazol-1-yl-acetic acid as a novel, reusable and water-soluble organocatalyst,,, Catal. Commun., 15: 123–126 (2011). using
• Bigi, F., Carloni, S., Frullanti, B., Maggi, R., Sartori, G., “A revision of the Biginelli reaction under solid acid dihydropyrimidines over montmorillonite KSF,,, Tetrahedron Lett., 40: 3465-3468 (1999). of
• Rani, V.R., Srinivas, N., Kishan, M.R., Kulkarni, S.J., cyclocondensation synthesis Green. Chem., 3: 305-306 (2001). the selective of
• Dondoni, A., Massi, A., “Parallel synthesis of dihydropyrimidinones polymer-supported scavengers under solvent-free conditions. A green chemistry approach to the Biginelli reaction,,, Tetrahedron Lett., 42: 7975– 7978 (2001). Yb(III)-resin and