N,N′-Dialkyl-4-Aryl-3,4-Dihydropyrimidinones and Thiones: Ceric Ammonium Nitrate Catalyzed Synthesis and Molecular Structure Determination by X-ray Crystallography
Chingrishon Kathing
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
Search for more papers by this authorSushil Kumar
Department of Chemistry, University of Delhi, Delhi, 110007 India
Search for more papers by this authorShokip Tumtin
Department of Chemistry, Kirori Mal College, University of Delhi, Delhi, 110007 India
Search for more papers by this authorNongthombam Geetmani Singh
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
Search for more papers by this authorJims World Star Rani
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
Search for more papers by this authorRidaphun Nongrum
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
Search for more papers by this authorCorresponding Author
Rishanlang Nongkhlaw
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
E-mail: [email protected]Search for more papers by this authorChingrishon Kathing
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
Search for more papers by this authorSushil Kumar
Department of Chemistry, University of Delhi, Delhi, 110007 India
Search for more papers by this authorShokip Tumtin
Department of Chemistry, Kirori Mal College, University of Delhi, Delhi, 110007 India
Search for more papers by this authorNongthombam Geetmani Singh
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
Search for more papers by this authorJims World Star Rani
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
Search for more papers by this authorRidaphun Nongrum
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
Search for more papers by this authorCorresponding Author
Rishanlang Nongkhlaw
Centre for Advanced Studies in Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022 India
E-mail: [email protected]Search for more papers by this authorAbstract
This work presents a microwave assisted solvent-free synthesis of N,N′-dialkyl-4-aryl-3,4-dihydropyrimidinones/thiones in the presence of Ceric Ammonium Nitrate (CAN) via direct condensation of aromatic aldehydes, β-keto ester, and N,N′-dialkylurea/thiourea. The highlights of the methodology adopted are (i) facile condensation of the reactants into product without any side-products, and (ii) short reaction time with high yield and good purity. All the compounds synthesized were characterized and established by spectroscopic techniques such as FTIR, 1H NMR, 13C NMR, and Mass. The structure of the compound is further corroborated by single crystal X-ray diffraction analysis.
Supporting Information
Supporting info item
| Filename | Description |
|---|---|
| jhet2735-sup-0001-supplementary material.docxWord 2007 document , 2.7 MB | Supporting info item |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References and Notes
- 1(a) Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwartz, J.; Malley, M. F. J Med Chem 1992, 35, 3254; (b) Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; Dimarco, J. D.; Gougoutas, J. Z.; Hedberg, A.; Malley, M.; Mccarthy, J. P.; Zhang, R.; Moreland, S. J Med Chem 1995, 38, 119.
- 2Schreiber, S. L. Science 2000, 287, 1964.
- 3Kappe, C. O. In Multicomponent Reactions J. Zhu; H. Bienaymé Eds.; Wiley-VCH: Weinheim, 2005, pp 95–120.
- 4Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem Eur J 2000, 6, 3321.
10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A CAS PubMed Web of Science® Google Scholar
- 5Domling, A.; Ugi, I. Angew Chem Int Ed 2000, 39, 3168.
10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U CAS PubMed Web of Science® Google Scholar
- 6Pelle, L.; Jason, T.; Benard, W.; Jacob, W. Tetrahedron 2001, 57, 9225.
- 7Helmut, M. H. Molecules 2009, 14, 4936.
- 8(a) Zhu, J. Eur J Org Chem 2003 1133; (b) Willy, B.; Mueller, T. J. J Curr Org Chem 2009, 13, 1777; (c) Bello, D.; Ramon, R.; Lavilla, R. Curr Org Chem 2010, 14, 332; (d) Jiang, B.; Rajale, T.; Wever, W.; Tu, S.-J.; Li, G. Chem Asian J 2010, 5, 2318.
- 9(a) Kappe, C. O. Tetrahedron 1993, 49, 6937; (b) Kappe, C. O. Acc Chem Res 2000, 33, 879.
- 10Atwal, K.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd, D. M. J Med Chem 1990, 33, 1510.
- 11(a) Janis, R. A.; Trigger, D. J J Med Chem 1983, 26, 775.
- 12Singh, K.; Arora, D.; Singh, S. Tetrahedron Lett 2006, 47, 4205.
- 13Sangram, G.; Sundarababu, B.; Burkhard, K. Green Chem 2011, 13, 1009.
- 14Ryabukhin, S. V.; Plaskon, A. S.; Ostapchuk, E. N.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2007, 3, 417.
- 15Mukhopadhyay, C.; Datta, A. J Het Chem 2010, 47(1), 136.
- 16(a) Folkers, K.; Johnson, T. B. J Am Chem Soc 1934, 56, 1374;
(b) George, T.; Tahilramani, R.; Mehta, D. V. Synthesis 1975, 6, 405;
10.1055/s-1975-23778 Google Scholar(c) Kappe, C. O.; Uray, G.; Roschger, P.; Linder, W.; Kartky, C.; Keller, W. Tetrahedron 1992, 48, 5473; (d) Kappe, C. O. Bioorg Med Chem Lett 2000, 10, 49.
- 17Jenner, G. Tetrahedron Lett 2004, 45, 6195.
- 18Stadler, A.; Kappe, C. O. J Comb Chem 2001, 3, 624.
- 19Hwu, J. R.; King, K.-Y. Curr Sci 2001, 81, 1043.
- 20(a) Tapaswi, P. K.; Mukhopadhyay, C. Arkivoc 2011, (x), 287; (b) Sridharan, V.; Menendez, J. C. Org Lett 2008, 10, 4303; (c) Chang, M.-Y.; Wu, T.-C.; Lin, C.-Y.; Hung, C. -Y. Tetrahedron Lett 2006, 47, 8347.
- 21(a) Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971; (b) Haggarty, S. J.; Mayer, T. U.; Miyamoto, D. T.; Fathi, R.; King, R. W.; Mitchison, T. J.; Schreiber, S. L. Chem Biol 2000, 7, 275.
- 22Panda, S. S.; Khanna, P.; Khanna, L. Curr Org Chem 2012, 16, 507.
- 23 CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (2011).
- 24Sheldrick, G. M. Acta Cryst 2008, A64, 112–122.
- 25Farrugia, L. J. WinGX Version 1.80.05, An integrated system of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data; Department of Chemistry, University of Glasgow (1997–2009).
