- About this Journal ·
- Abstracting and Indexing ·
- Aims and Scope ·
- Article Processing Charges ·
- Author Guidelines ·
- Bibliographic Information ·
- Citations to this Journal ·
- Contact Information ·
- Editorial Board ·
- Editorial Workflow ·
- Free eTOC Alerts ·
- Publication Ethics ·
- Recently Accepted Articles ·
- Reviewers Acknowledgment ·
- Submit a Manuscript ·
- Subscription Information ·
- Table of Contents
ISRN Organic Chemistry
Volume 2012 (2012), Article ID 342738, 7 pages
“On-Water” Catalyst-Free Ecofriendly Synthesis of the Hantzsch Dihydropyridines
1Department of Chemistry, Taki Government College, North 24 Pgs 743 429, India
2Department of Chemistry, Surendranath Evening College, Kolkata 700 009, India
3Department of Chemistry, Jadavpur University, Kolkata 700 032, India
Received 5 April 2012; Accepted 13 May 2012
Academic Editors: G. Giambastiani, G. Kirsch, and I. Tellitu
Copyright © 2012 Amit Pramanik et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- D. Mauzerall and F. H. Westheimer, “1-Benzyldihydronicotinamide—a model for reduced DPN,” Journal of the American Chemical Society, vol. 77, no. 8, pp. 2261–2264, 1955.
- V. Klusa, “Cerebrocrast. Neuroprotectant, cognition enhancer,” Drugs of the Future, vol. 20, no. 2, pp. 135–138, 1995.
- R. S. Kumar, A. Idhayadhulla, A. J. A. Nasser, and J. Selvin, “Synthesis and anticoagulant activity of a new series of 1,4-dihydropyridine derivatives,” European Journal of Medicinal Chemistry, vol. 46, no. 2, pp. 804–810, 2011.
- R. Boer and V. Gekeler, “Chemosensitizers in tumor therapy: new compounds promise better efficacy,” Drugs of the Future, vol. 20, no. 5, pp. 499–509, 1995.
- F. Bossert, H. Meyer, and E. Wehinger, “4-Aryldihydropyridines, a new class of highly active calcium antagonists,” Angewandte Chemie International Edition, vol. 20, no. 9, pp. 762–769, 1981.
- N. Nakamichi, Y. Kawashita, and M. Hayashi, “Activated carbon-promoted oxidative aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines using molecular oxygen,” Synthesis, no. 7, pp. 1015–1020, 2004.
- B. Han, Q. Liu, Z. Liu et al., “A metal-free catalytic aerobic aromatization of Hantzsch 1,4-dihydropyridines by N-hydroxyphthalimide,” Synlett, no. 15, pp. 2333–2334, 2005.
- A. McKillop and A. J. Boulton, “Synthesis of six-membered rings,” in Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees, Eds., vol. 2, pp. 87–88, Pergamon Press, London, UK, 1984.
- L. Öhberg and J. Westman, “An efficient and fast procedure for the Hantzsch dihydropyridine synthesis under microwave conditions,” Synlett, no. 8, pp. 1296–1298, 2001.
- J. S. Yadav, B. V. Subba Reddy, P. Thirupati, et al., “Unprecedented synthesis of Hantzsch 1,4-dihydropyridines under biginelli reaction conditions,” Synthetic Communications, vol. 31, no. 3, pp. 425–430, 2001.
- M. Anniyappam, D. Muralidharan, and P. T. Perumal, “Synthesis of Hantzsch 1, 4-dihydropyridines under microwave irradiation,” Synthetic Communications, vol. 32, no. 4, pp. 659–663, 2002.
- R. S. Varma, Advances in Green Chemistry: Chemical Syntheses Using Microwave Irradiation, AstraZeneca Research Foundation India, Bangalore, India, 2003.
- G. V. M. Sharma, K. L. Reddy, P. S. Lakshmi, and P. R. Krishna, “‘In situ’ generated “HCl”—an efficient catalyst for solvent-free Hantzsch reaction at room temperature: Synthesis of new dihydropyridine glycoconjugates,” Synthesis, no. 1, Article ID P05205SS, pp. 55–58, 2006.
- K. L. Bridgwood, G. E. Veitch, and S. V. Ley, “Magnesium nitride as a convenient source of ammonia: preparation of dihydropyridines,” Organic Letters, vol. 10, no. 16, pp. 3627–3629, 2008.
- B. Khalili, P. Jajarmi, B. Eftekhari-Sis, and M. M. Hashemi, “Novel one-pot, three-component synthesis of new 2-alkyl-5-aryl-(1H)-pyrrole-4-ol in water,” Journal of Organic Chemistry, vol. 73, no. 6, pp. 2090–2095, 2008.
- M. M. Heravi, S. Sadjadi, H. A. Oskooie, R. H. Shoar, and F. F. Bamoharram, “A direct oxidative route for the synthesis of pyrimidines using heteropolyacids,” Tetrahedron Letters, vol. 50, no. 6, pp. 662–666, 2009.
- G. Sabitha, G. S. K. K. Reddy, C. S. Reddy, and J. S. Yadav, “A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature,” Tetrahedron Letters, vol. 44, no. 21, pp. 4129–4131, 2003.
- N. Tewari, N. Dwivedi, and R. P. Tripathi, “Tetrabutylammonium hydrogen sulfate catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines,” Tetrahedron Letters, vol. 45, no. 49, pp. 9011–9014, 2004.
- J. H. Lee, “Synthesis of Hantsch 1,4-dihydropyridines by fermenting bakers' yeast,” Tetrahedron Letters, vol. 46, no. 43, pp. 7329–7330, 2005.
- A. Kumar and R. A. Maurya, “Efficient synthesis of Hantzsch esters and polyhydroquinoline derivatives in aqueous micelles,” Synlett, no. 6, pp. 883–885, 2008.
- A. Debache, R. Boulcina, A. Belfaitah, S. Rhouati, and B. Carboni, “One-pot synthesis of 1,4-dihydropyridines via a phenylboronic acid catalyzed Hantzsch three-component reaction,” Synlett, no. 4, pp. 509–512, 2008.
- A. Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati, and B. Carboni, “An efficient one-step synthesis of 1,4-dihydropyridines via a triphenylphosphine-catalyzed three-component Hantzsch reaction under mild conditions,” Tetrahedron Letters, vol. 50, no. 37, pp. 5248–5250, 2009.
- S. Tang, R. Bourne, R. Smith, and M. Poliakoff, “The 24 principles of green engineering and green chemistry: ‘Improvements Productively’,” Green Chemistry, vol. 10, no. 3, pp. 268–269, 2008.
- R. Breslow, “Hydrophobic effects on simple organic reactions in water,” Accounts of Chemical Research, vol. 24, no. 6, pp. 159–164, 1991.
- J. B. F. N. Engberts and M. J. Blandamer, “Understanding organic reactions in water: from hydrophobic encounters to surfactant aggregates,” Chemical Communications, no. 18, pp. 1701–1708, 2001.
- S. Mecking, A. Held, and F. M. Bauers, “Aqueous catalytic polymerization of olefins,” Angewandte Chemie International Edition, vol. 41, no. 4, pp. 544–561, 2002.
- N. E. Leadbeater and M. Marco, “Rapid and amenable Suzuki coupling reaction in water using microwave and conventional heating,” Journal of Organic Chemistry, vol. 68, no. 3, pp. 888–892, 2003.
- K. Yamaguchi, M. Matsushita, and N. Mizuno, “Efficient hydration of nitriles to amides in water, catalyzed by ruthenium hydroxide supported on alumina,” Angewandte Chemie International Edition, vol. 43, no. 12, pp. 1576–1580, 2004.
- S. Minakata, D. Kano, Y. Oderaotoshi, and M. Komatsu, “Silica-water reaction media: its application to the formation and ring opening of aziridines,” Angewandte Chemie International Edition, vol. 43, no. 1, pp. 79–81, 2004.
- N. E. Leadbeater, “Fast, easy, clean chemistry by using water as a solvent and microwave heating: the Suzuki coupling as an illustration,” Chemical Communications, vol. 23, pp. 2881–2902, 2005.
- S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, and K. B. Sharpless, “‘On water’: unique reactivity of organic compounds in aqueous suspension,” Angewandte Chemie International Edition, vol. 44, no. 21, pp. 3275–3279, 2005.
- H. Buchammagari, Y. Toda, M. Hirano, H. Hosono, D. Takeuchi, and K. Osakada, “Room temperature-stable electride as a synthetic organic reagent: application to pinacol coupling reaction in aqueous media,” Organic Letters, vol. 9, no. 21, pp. 4287–4289, 2007.
- N. Shapiro and A. Vigalok, “Highly efficient organic reactions “on water”, “in water”, and both,” Angewandte Chemie International Edition, vol. 47, no. 15, pp. 2849–2852, 2008.
- Q.-Y. Zhang, B.-K. Liu, W.-Q. Chen, Q. Wu, and X. F. Lin, “A green protocol for synthesis of benzo-fused N,S-, N,O- and N,N-heterocycles in water,” Green Chemistry, vol. 10, no. 9, pp. 972–977, 2008.
- L. D. S. Yadav, S. Singh, and V. K. Rai, “Catalyst-free, step and pot economic, efficient mercaptoacetylative cyclisation in H2O: synthesis of 3-mercaptocoumarins,” Green Chemistry, vol. 11, no. 6, pp. 878–882, 2009.
- J. W. Yang, M. T. Hechavarria Fouseca, and B. List, “A metal-free transfer hydrogenation: organocatalytic conjugate reduction of α, β-unsaturated aldehydes,” Angewandte Chemie International Edition, vol. 43, no. 48, pp. 6660–6662, 2004.
- A. E. Abdalla, D. Tirzite, G. Tirzitis, and J. P. Roozen, “Antioxidant activity of 1,4-dihydropyridine derivatives in β-carotene-methyl linoleate, sunflower oil and emulsions,” Food Chemistry, vol. 66, no. 2, pp. 189–195, 1999.
- R. A. Olek, W. Ziolkowski, J. J. Kaczor, L. Greci, J. Popinigis, and J. Antosiewicz, “Antioxidant activity of NADH and its analogue—an in vitro study,” Journal of Biochemistry and Molecular Biology, vol. 37, no. 4, pp. 416–421, 2004.
- B. E. Norcross, G. Clement, and M. Weinstein, “The Hantzsch pyridine synthesis: a factorial design experiment for the introductory organic laboratory,” Journal of Chemical Education, vol. 46, no. 10, pp. 694–695, 1969.
- A. P. Dicks, “A review of aqueous organic reactions for the undergraduate teaching laboratory,” Green Chemistry Letters and Reviews, vol. 2, no. 1, pp. 9–21, 2009.
- Material safety data sheet, http://msds.chem.ox.ac.uk/AM/ammonium_acetate.
- Material safety data sheet, http://msds.chem.ox.ac.uk/AM/ammonia_anhydrous.
- Material safety data sheet, http://msds.chem.ox.ac.uk/AM/ammonia_hydroxide.
- Material safety data sheet, http://msds.chem.ox.ac.uk/PA/paraformaldehyde.
- Material safety data sheet, http://msds.chem.ox.ac.uk/FO/formaldehyde.
- F. Tamaddon, Z. Razmi, and A. A. Jafari, “Synthesis of 3, 4-dihydropyrimidin-2(1H)-ones and 1, 4-dihydropyridines using ammonium carbonate in water,” Tetrahedron Letters, vol. 51, no. 8, pp. 1187–1189, 2010.