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

Abstract

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

Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid

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

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.

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
There are 28 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Chemistry
Authors

Rahim Hekmatshoar

Mojgan Kargar This is me

Zahra Hashemı This is me

Fereshteh Golı This is me

Abdoljalil Mostasharı This is me

Publication Date July 19, 2012
Published in Issue Year 2012 Volume: 25 Issue: 3

Cite

APA Hekmatshoar, R., Kargar, M., Hashemı, Z., Golı, F., et al. (2012). Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid. Gazi University Journal of Science, 25(3), 617-621.
AMA Hekmatshoar R, Kargar M, Hashemı Z, Golı F, Mostasharı A. Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid. Gazi University Journal of Science. July 2012;25(3):617-621.
Chicago Hekmatshoar, Rahim, Mojgan Kargar, Zahra Hashemı, Fereshteh Golı, and Abdoljalil Mostasharı. “Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid”. Gazi University Journal of Science 25, no. 3 (July 2012): 617-21.
EndNote Hekmatshoar R, Kargar M, Hashemı Z, Golı F, Mostasharı A (July 1, 2012) Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid. Gazi University Journal of Science 25 3 617–621.
IEEE R. Hekmatshoar, M. Kargar, Z. Hashemı, F. Golı, and A. Mostasharı, “Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid”, Gazi University Journal of Science, vol. 25, no. 3, pp. 617–621, 2012.
ISNAD Hekmatshoar, Rahim et al. “Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid”. Gazi University Journal of Science 25/3 (July 2012), 617-621.
JAMA Hekmatshoar R, Kargar M, Hashemı Z, Golı F, Mostasharı A. Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid. Gazi University Journal of Science. 2012;25:617–621.
MLA Hekmatshoar, Rahim et al. “Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid”. Gazi University Journal of Science, vol. 25, no. 3, 2012, pp. 617-21.
Vancouver Hekmatshoar R, Kargar M, Hashemı Z, Golı F, Mostasharı A. Novel and Efficient Organocatalytic Biginelli Reaction Using 2-Ethylhexanoic Acid. Gazi University Journal of Science. 2012;25(3):617-21.