Abstract
The combination of the Biginelli reaction with click chemistry has been used for the one-pot synthesis of 1,2,3-triazole linked dihydropyrimidinones from azides, aromatic aldehydes containing a propargyl ether group, urea, and 1,3-dicarbonyl compounds using Cu(OAc)2/sodium ascorbate as catalyst in acetic acid under mild reaction conditions.
Similar content being viewed by others
References
Huisgen R (1984) In: Padwa A (ed) 1,3-Dipolar cycloaddition chemistry. Wiley, New York, pp 1–117
Sha C-K, Mohanakrishnan AK (2003) In: Padwa A, Pearson WH (eds) Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products. Wiley, New York, pp 623–680
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem Int Ed 41: 2596–2599. doi:10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40: 2004–2021. doi:10.1002/1521-3773(20010601)
Lee LV, Mitchell ML, Huang SJ, Fokin VV, Sharpless KB, Wong CH (2003) A potent and highly selective inhibitor of human α-1,3-fucosyltransferase via click chemistry. J Am Chem Soc 125: 9588–9589. doi:10.1021/ja0302836
Brik A, Muldoon J, Lin YC, Elder JH, Goodsell DS, Olson AJ, Fokin V, Sharpless KB, Wong CH (2003) Rapid diversity-oriented synthesis in microtiter plates for in situ screening of HIV protease inhibitors. ChemBioChem 4: 1246–1248. doi:10.1002/cbic.200300724
Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG (2003) Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. J Am Chem Soc 125: 3192–3193. doi:10.1021/ja021381e
Speers AE, Adam GC, Cravatt BF (2003) Activity-based protein profiling in vivo using a copper(I) catalyzed azide-alkyne [3 + 2] cycloaddition. J Am Chem Soc 125: 4686–4687. doi:10.1021/ja034490h
Link AJ, Tirell DA (2003) Cell surface labeling of Escherichia coli via copper(I)-catalyzed [3+2] cycloaddition. J Am Chem Soc 125: 11164–11165. doi:10.1021/ja036765z
Burley GA, Gierlich J, Mofid MR, Nir H, Tal S, Eichen Y, Carell TJ (2006) Directed DNA metallization. J Am Chem Soc 128: 1398–1399. doi:10.1021/ja055517v
Wu P, Feldmann AK, Nugent AK, Hawker CJ, Scheel A, Voit B, Pyun J, Frechet JMJ, Sharpless KB, Fokin VV (2004) Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes. Angew Chem Int Ed 43: 3928–3932. doi:10.1002/anie.200454078
Helms B, Mynar JL, Hawker CJ, Frechet JM (2004) Dendronized linear polymers via “click chemistry”. J Am Chem Soc 126: 15020–15021. doi:10.1021/ja044744e
van Steenis DJVC, David ORP, van Strijdonck GPF, van Maarseveen J H, Reek JNH (2005) Click-chemistry as an efficient synthetic tool for the preparation of novel conjugated polymers. Chem Commun 29: 4333–4335. doi:10.1039/b507776a
Hawker CJ, Wooley KL (2005) The convergence of synthetic organic and polymer chemistries. Science 309: 1200–1205. doi:10.1126/science.1109778
Devadoss A, Chidsey CED (2007) Azide-modified graphitic surfaces for covalent attachment of alkyne-terminated molecules by “click” chemistry. J Am Chem Soc 129: 5370–5371. doi:10.1021/ja071291f
Ramachary DB, Barbas CF III (2004) Towards organo-click chemistry: development of organocatalytic multicomponent reactions through combinations of aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions. Chem Eur J 10: 5323–5331. doi:10.1002/chem.200400597
Akritopoulou-Zanze I, Gracias V, Djuric SW (2004) A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions. Tetrahedron Lett 45: 8439–8441. doi:10.1016/j.tetlet.2004.09.117
Gracias V, Darczak D, Gasiecki AF, Djuric SW (2005) Synthesis of fused triazolo-imidazole derivatives by sequential van Leusen/alkyne-azide cycloaddition reactions. Tetrahedron Lett 46: 9053–9056. doi:10.1016/j.tetlet.2005.10.090
Sreedhar B, Reddy PS, Kumar NS (2006) Cu(I)-catalyzed one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles via nucleophilic displacement and 1,3-dipolar cycloaddition. Tetrahedron Lett 47: 3055–3058. doi:10.1016/j.tetlet.2006.03.007
Chandrasekhar S, Basu D, Rambabu C (2006) Three-component coupling of alkynes, Baylis-Hillman adducts and sodium azide: a new synthesis of substituted triazoles. Tetrahedron Lett 47: 3059–3063. doi:10.1016/j.tetlet.2006.03.037
Khanetskyy B, Dallinger D, Kappe CO (2004) Combining biginelli multicomponent and click chemistry: generation of 6-(1,2,3-triazol-1-yl)-dihydropyrimidone libraries. J Comb Chem 6: 884–892. doi:10.1021/cc0498938
Ashok M, Holla BS, Kumari NS (2007) Convenient one pot synthesis of some novel derivatives of thiazolo[2,3-b]dihydropyrimidinone possessing 4-methylthiophenyl moiety and evaluation of their antibacterial and antifungal activities. Eur J Med Chem 42: 380–385. doi:10.1016/j.ejmech.2006.09.003
Hurst EW, Hull R (1961) Two new synthetic substances active against viruses of the psittacosis-lymphogranuloma-trachoma group. J Med Pharm Chem 3: 215–229
Bahekar SS, Shinde DB (2004) Synthesis and anti-inflammatory activity of some [4,6-(4-substituted aryl)-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetic acid derivatives. Bioorg Med Chem Lett 14: 1733–1736. doi:10.1016/j.bmcl.2004.01.039
Magerramov AM, Kurbanova MM, Abdinbekova RT, Rzaeva IA, Farzaliev VM, Allakhverdiev MA (2006) Synthesis and antioxidative properties of some 3,4-dihydropyrimidin-2(1H) ones (-thiones). Russ J Appl Chem 79: 787–790. doi:10.1134/S107042720605017X
Kappe CO (2000) Biologically active dihydropyrimidones of the Biginelli-type—a literature survey. Eur J Med Chem 35: 1043–1052. doi:10.1016/S0223-5234(00)01189-2
Grover GJ, Dzwonczyk S, McMullen DM, Normandin DE, Parham CS, Sleph PG, Moreland S (1995) Pharmacologic profile of the dihydropyrimidine calcium channel blockers SQ 32,547 and SQ 32,946. J Cardiovasc Pharmacol 26: 289–294
Dabiri M, Salehi P, Bahramnejad M, Sherafat F (2010) Synthesis of diheterocyclic compounds based on triazolyl methoxy phenylquinazolines via a one-pot four-component-click reaction. J Comb Chem 12: 638–642. doi:10.1021/cc100043z
Salehi P, Dabiri M, Zolfigol MA, Bodaghi Fard MA (2003) Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett 44: 2889–2891. doi:10.1016/S0040-4039(03)00436-2
Salehi P, Dabiri M, Zolfigol MA, Bodaghi Fard MA (2003) Efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones over silica sulfuric acid as a reusable catalyst under solvent-free conditions. Heterocycles 60: 2435–2440. doi:10.3987/COM-03-9837
Bräse S, Gil C, Knepper K, Zimmermann V (2005) Organic azides: an exploding diversity of a unique class of compounds. Angew Chem Int Ed 44: 5188–5240. doi:10.1002/anie.200400657
Scriven EFV, Turnbull K (1988) Azides: their preparation and synthetic uses. Chem Rev 88: 297–368. doi:10.1021/cr00084a001
Sandler S, Karo W (1971) Organic functional group preparations. Academic Press, New York, pp 268–284
Karaev SF, Garaeva ShV (1980) 1. Prop-2-ynyl ethers. Russ Chem Rev 49: 865–879. doi:10.1070/RC1980v049n09ABEH002512
Frixa C, Mahon MF, Thompson AS, Threadgill MD (2003) Synthesis of meso-substituted porphyrins carrying carboranes and oligo(ethylene glycol) units for potential applications in boron neutron capture therapy. Org Biomol Chem 1: 306–317. doi:10.1039/b209534c
Author information
Authors and Affiliations
Corresponding author
Electronic Supplementary Material
The Below is the Electronic Supplementary Material.
Rights and permissions
About this article
Cite this article
Salehi, P., Dabiri, M., Koohshari, M. et al. One-pot synthesis of 1,2,3-triazole linked dihydropyrimidinones via Huisgen 1,3-dipolar/Biginelli cycloaddition. Mol Divers 15, 833–837 (2011). https://doi.org/10.1007/s11030-011-9313-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-011-9313-6