Copper-catalyzed cascade preparation of dihydropyrimidin-4-ones from N -(Prop-2-yn-1-yl)amides and azides

Journal of Organic Chemistry

Volumn 78, Issue 17, 2013, Pages 8816-8820

  Wang, Jinjin ^a   Wang, Jing ^a   Lu, Ping ^a   Wang, Yanguang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE PROCESS; COPPER-CATALYZED REACTIONS; KETENIMINES; NUCLEOPHILIC ADDITIONS;

ADDITION REACTIONS; AMIDES; COPPER;

CATALYSIS;

ALKYNE DERIVATIVE; AMIDE; AZIDE; COPPER; DIHYDROPYRIMIDIN 4 ONE DERIVATIVE; IMINE; KETENIMINE DERIVATIVE; N (PROP 2 YN 1 YL)AMIDE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REPRODUCIBILITY;

AMIDES; AZIDES; CATALYSIS; COPPER; MOLECULAR STRUCTURE; PYRIMIDINONES;

EID: 84883818826     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401094j     Document Type: Article

References (32)

1. Wan, J.-P.; Pan, Y. Mini Rev. Med. Chem. 2012, 12, 337
2. Lewis, R. W.; Mabry, J.; Polisar, J. G.; Eagen, K. P.; Ganem, B.; Hess, G. P. Biochemistry 2010, 49, 4841
3. Jeong, L. S.; Buenger, G.; McCormack, J. J.; Cooney, D. A.; Zhang, H.; Marquez, V. E. J. Med. Chem. 1998, 41, 2572
4. Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971
5. Mai, A.; Sbardella, G.; Artico, M.; Ragno, R.; Massa, S.; Novellino, E.; Greco, G.; Lavecchia, A.; Musiu, C.; La Colla, M.; Murgioni, C.; La Colla, P.; Loddo, R. J. Med. Chem. 2001, 44, 2544
6. Mugnaini, C.; Alongi, M.; Togninelli, A.; Gevaiya, H.; Brizzi, A.; Manetti, F.; Bernardini, C.; Angeli, L.; Tafi, A.; Bellucci, L.; Corelli, F.; Massa, S.; Maga, G.; Samuele, A.; Facchini, M.; Clotet-Codina, I.; Armand-Ugon, M.; Este, J. A.; Botta, M. J. Med. Chem. 2007, 50, 6580
7. Rotili, D.; Tarantino, D.; Artico, M.; Nawrozkij, M. B.; Gonzalez-Ortega, E.; Clotet, B.; Samuele, A.; Este, J. A.; Maga, G.; Mai, A. J. Med. Chem. 2011, 54, 3091
8. Gahr, M.; Kölle, M. A.; Schönfeldt-Lecuona, C.; Lepping, P.; Freudenmann, R. W. Drug Des. Devel. Ther. 2011, 5, 125
9. Riva, R.; Banfi, L.; Castaldi, G.; Ghislieri, D.; Malpezzi, L.; Musumeci, F.; Tufaro, R.; Rasparini, M. Eur. J. Org. Chem. 2011, 231
10. Kunio, I.; Yoshiko, K.; Yuji, H. J. Heterocyclic Chem. 2005, 42, 583
11. Dzhavakhishvili, S. G.; Gorobets, N. Y.; Shishkina, S. V.; Shishkin, O. V.; Dedenko, S. M.; Groth, U. M. J. Comb. Chem. 2009, 11, 508
12. Ostras, K. S.; Gorobets, N. Y.; Desenko, S. M.; Musatov, V. I. Mol. Divers. 2006, 10, 483
13. Mirza-Aghayan, M.; Baie Lashaki, T.; Rahimifard, M.; Boukherroub, R.; Tarlani, A. A. J. Iran. Chem. Soc. 2011, 8, 280
14. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
15. Bae, I.; Han, H.; Chang, S. J. Am. Chem. Soc. 2005, 127, 2038
16. Lu, P.; Wang, Y. Chem. Soc. Rev. 2012, 41, 5687
17. Kim, S. H.; Park, S. H.; Choi, J. H.; Chang, S. Chem.-Asian J. 2011, 6, 2618
18. Yoo, E. J.; Chang, S. Curr. Org. Chem. 2009, 13, 1766
19. Lu, P.; Wang, Y. G. Synlett 2010, 2, 165
20. Cui, S. L.; Lin, X. F.; Wang, Y. G. Org. Lett. 2006, 8, 4517
21. Cui, S. L.; Wang, J.; Wang, Y. G. Tetrahedron 2008, 64, 487
22. Shen, Y.; Cui, S. L.; Wang, J.; Chen, X. P.; Lu, P.; Wang, Y. G. Adv. Synth. Catal. 2010, 352, 1139
23. Cui, S. L.; Wang, J.; Wang, Y. G. Org. Lett. 2007, 9, 5023
24. Li, Y.; Hong, D.; Zhu, Y. X.; Lu, P.; Wang, Y. G. Tetrahedron 2011, 67, 8086
25. Song, W. Z.; Lu, W.; Wang, J.; Lu, P.; Wang, Y. G. J. Org. Chem. 2010, 75, 3481
26. Song, W. Z.; Lei, M.; Shen, Y.; Cai, S. Y.; Lu, W.; Lu, P.; Wang, Y. G. Adv. Synth. Catal. 2010, 352, 2432
27. Wang, J.; Wang, J.; Zhu, Y.; Lu, P.; Wang, Y. G. Chem. Commun. 2011, 47, 3275
28. Yoo, E. J.; Chang, S. Org. Lett. 2008, 10, 1163
29. For ORTEPs of compound 3a, please see the Supporting Information. CCDC 943090 (3a) contains supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
30. Messina, F.; Botta, M.; Corelli, F.; Schneider, M. P.; Fazio, F. J. Org. Chem. 1999, 64, 3767
31. Beccalli, E. M.; Borsini, E.; Broggini, G.; Palmisano, G.; Sottocornola, S. J. Org. Chem. 2008, 73, 4746
32. McElwee-White, L.; Dougherty, D. A. J. Am. Chem. Soc. 1984, 106, 3466