Abstract
The synthesis of quinazoline-2,4(1H,3H)-diones from carbon dioxide and 2-aminobenzonitriles using MgO/ZrO2 as a novel and efficient heterogeneous base catalyst is reported. The synthesized MgO/ZrO2 catalyst was characterized by XRD, FTIR and its basic properties were measured using CO2 temperature programed desorption analysis. The effects of various reaction parameters were investigated in detail. A wide variety of aromatic aminobenzonitriles and five member N-heterocyclic carbonitriles were synthesized using this protocol.
Similar content being viewed by others
References
Arakawa H, Aresta M, Armor JN, Barteau MA, Beckman EJ, Bell AT, Bercaw JE, Creutz C, Dinjus E, Dixon DA, Domen K, DuBois DL, Eckert J, Fujita E, Gibson DH, Goddard WA, Goodman DW, Keller J, Kubas GJ, Kung HH, Lyons JE, Manzer LE, Marks TJ, Morokuma K, Nicholas KM, Periana R, Que L, Rostrup-Nielson J, Sachtler WMH, Schmidt LD, Sen A, Somorjai GA, Stair PC, Stults BR, Tumas W (2001) Chem Rev 101:953
Patil YP, Tambade PJ, Jagtap SR, Bhanage BM (2009) Front Chem Eng China. doi 10:1007/s 11705-009-0227-0 (in press)
Inoue S, Yamazaki N (1982) Organic and bio-organic chemistry of carbon dioxide. Kodansha, Tokyo
Aresta A, Forti Reidal G (1987) Carbon dioxide as a sources of carbon; Reidal: NATO ASI series C 206
Goto S, Tsuboi H, Kagara K (1993) Chem Express 8:761
Kagara K, Goto S, Tsuboi H (1989) JP 1,025,767, Chem Abstr (1989) 111:97274
Mohri S (2001) J Synth Org Chem Jpn 59:514
Budavari S et al. (1996) Merck index, 12th edn. Merck & Co.; Inc., Whitehouse Station, p 7897
Budavari S et al. (1996) Merck index, 12th edn. Merck & Co.; Inc., Whitehouse Station, p 1512
Budavari S et al. (1996) Merck index, 12th edn. Merck & Co.; Inc., Whitehouse Station, p 3489
Pastor G, Blanchard C, Montginoul C, Torreilles E, Giral L, Texier A (1795) Bull Soc Chim Fr 1331
Khalifa M, Osman AN, Ibrahim MG, Ossaman ARE, Ismail MA (1982) Pharmazie 37:115
Michman M, Patai S, Wiesel Y (1978) Org Prep Proced Int 10:13
Lange NA, Sheibley FE (1943) Org Synth Coll Vol ll Wiley, London, p 79
Vorbrueggen H, Krolikiewicz K (1994) Tetrahedron 50:6549
Mizuno T, Okamoto N, Ito T, Miyata T (2000) Tetrahedron Lett 41:1051
Mizuno T, Okamoto N, Ito T, Miyata T (2000) Heteroat Chem ll:428
Mizuno T, Ishino Y (2002) Tetrahedron 58:3155
Mizuno T, Iwai T, Ishino Y (2004) Tetrahedron Lett 45:7073
Mizuno T, Mihara M, Nakai T, Iwai T, Ito T (2007) Synthesis 16:2524
Patil YP, Tambade PJ, Jagtap SR, Bhanage BM (2008) Green Chem Lett. Rev 1(2):127
Patil YP, Tambade PJ, Deshmukh KM, Bhanage BM (2009) Catal Today. doi:10.1016/j.cattod.2009.06.010 (in press)
Chaubal N, Sawant M (2004) Ind J Chem 43A:1427
Gavande MB, Jayaram RV (2006) Cat Com 7:931
Lee MH, Park DG (2003) Bull Korean Chem Soc 24:1437
Zao L, Zao J, Luo M, Liu G, Song J, Zang Y (2005) Catal Commun 6:617
Bhanage BM, Fujita S, Ikushima Y, Arai M (2004) Green Chem 6:78
Bhanage BM, Fujita S, Ikushima Y, Arai M (2003) Green Chem 5:340
Jagtap SR, Raje VP, Samant SD, Bhanage BM (2006) J Mol Catal A Chem 266:69
Patil YP, Tambade PJ, Nandurkar NS, Bhanage BM (2008) Catal Commun 9:2068
Patil YP, Tambade PJ, Jagtap SR, Bhanage BM (2008) J Mol Catal A Chem 289:14
Sun J, Wang L, Zang S, Li Z, Zhang X, Dai W, Mori R (2006) J Mol Catal A Chem 256:295
Acknowledgments
The authors are thankful for financial support for this work from the Council of Scientific & Industrial Research (CSIR), India though Grant no. 09/019(0073)2009-EMR-1.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Patil, Y.P., Tambade, P.J., Parghi, K.D. et al. Synthesis of Quinazoline-2,4(1H,3H)-Diones from Carbon dioxide and 2-Aminobenzonitriles Using MgO/ZrO2 as a Solid Base Catalyst. Catal Lett 133, 201–208 (2009). https://doi.org/10.1007/s10562-009-0126-5
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-009-0126-5