Combining biginelli multicomponent and click chemistry: Generation of 6-(1,2,3-triazol-1-yl)-dihydropyrimidone libraries

Journal of Combinatorial Chemistry

Volumn 6, Issue 6, 2004, Pages 884-892

  Khanetskyy, Bogdan ^a   Dallinger, Doris ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AZIDE; COPPER; POLYMER; PYRIMIDINE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; BIGINELLI REACTION; BROMINATION; CATALYSIS; COMBINATORIAL CHEMISTRY; CYCLOADDITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICROWAVE RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 9344238756     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0498938     Document Type: Article

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14. For recent applications of Cu(I)-catalyzed azide acetylene cycloadditions, see: (a) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057. (b) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (c) Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588-9589. (c) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165. (d) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687. (e) Speers, A. E.; Cravatt, B. F. Chem. Biol. 2004, 11, 535-546. (f) Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem. 2003, 68, 609-612. (g) Löber, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett. 2003, 5, 1753-1755. (g) Tornøe, C. W.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H.; Meldal, M. J. Comb. Chem. 2004, 6, 312-324.
15. For recent applications of Cu(I)-catalyzed azide acetylene cycloadditions, see: (a) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057. (b) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (c) Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588-9589. (c) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165. (d) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687. (e) Speers, A. E.; Cravatt, B. F. Chem. Biol. 2004, 11, 535-546. (f) Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem. 2003, 68, 609-612. (g) Löber, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett. 2003, 5, 1753-1755. (g) Tornøe, C. W.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H.; Meldal, M. J. Comb. Chem. 2004, 6, 312-324.
16. For recent applications of Cu(I)-catalyzed azide acetylene cycloadditions, see: (a) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057. (b) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (c) Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588-9589. (c) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165. (d) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687. (e) Speers, A. E.; Cravatt, B. F. Chem. Biol. 2004, 11, 535-546. (f) Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem. 2003, 68, 609-612. (g) Löber, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett. 2003, 5, 1753-1755. (g) Tornøe, C. W.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H.; Meldal, M. J. Comb. Chem. 2004, 6, 312-324.
17. For recent applications of Cu(I)-catalyzed azide acetylene cycloadditions, see: (a) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057. (b) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (c) Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588-9589. (c) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165. (d) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687. (e) Speers, A. E.; Cravatt, B. F. Chem. Biol. 2004, 11, 535-546. (f) Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem. 2003, 68, 609-612. (g) Löber, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett. 2003, 5, 1753-1755. (g) Tornøe, C. W.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H.; Meldal, M. J. Comb. Chem. 2004, 6, 312-324.
18. For recent applications of Cu(I)-catalyzed azide acetylene cycloadditions, see: (a) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057. (b) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (c) Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588-9589. (c) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165. (d) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687. (e) Speers, A. E.; Cravatt, B. F. Chem. Biol. 2004, 11, 535-546. (f) Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem. 2003, 68, 609-612. (g) Löber, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett. 2003, 5, 1753-1755. (g) Tornøe, C. W.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H.; Meldal, M. J. Comb. Chem. 2004, 6, 312-324.
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56. For a recent example of microwave-assisted bromide-azide displacement, see the following: Singh, P. N. D.; Muthukrishnan, S.; Murthy, R. S.; Klima, R. F.; Mandel, S. M.; Hawk, M.; Yarbrough, N.; Gudmundsdottir, A. D. Tetrahedron Lett. 2003, 44, 9169-9171.
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58. (b) Kappe, C. O.; Stadler, A. In Combinatorial Chemistry, Part B; Bunin, B. B., Morales, G., Eds.; Elsevier: Amsterdam, 2003; Chapter 11, pp 197-223.
59. Sodium azide is known to form a complex with Cu ions and dimethylformamide (DMF). For details, see: (a) Baruah, S. D.; Dass, N. N. Makromol. Chem. 1981, 182, 3591-3601. (b) Maggio, F.; Cavasino, F. P. Ann. Chim. 1961, 51, 1392-1398.
60. Sodium azide is known to form a complex with Cu ions and dimethylformamide (DMF). For details, see: (a) Baruah, S. D.; Dass, N. N. Makromol. Chem. 1981, 182, 3591-3601. (b) Maggio, F.; Cavasino, F. P. Ann. Chim. 1961, 51, 1392-1398.