A novel domino synthesis of quinazolinediones by palladium-catalyzed double carbonylation

Chemistry - A European Journal

Volumn 20, Issue 28, 2014, Pages 8541-8544

  Li, Haoquan ^a   Li, Wanfang ^a   Spannenberg, Anke ^a   Baumann, Wolfgang ^a   Neumann, Helfried ^a   Beller, Matthias ^a   Wu, Xiao Feng ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

carbonylation; coupling; domino reactions; multicomponent reactions; palladium

Indexed keywords

CATALYSIS; COUPLINGS; CYCLIZATION; PALLADIUM; REACTION KINETICS;

DOMINO REACTIONS; MULTI-COMPONENT REACTIONS; PALLADIUM-CATALYZED;

CARBONYLATION;

EID: 84903745542     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403417     Document Type: Article

References (51)

1. A. R. Katritzky, C. W. Rees, Comprehensive Heterocyclic Chemistry: The Structure, Reaction, Synthesis and Uses of Heterocyclic Compounds, Pergamon Press, New York, 1984
2. L. D. Quin, J. A. Tyrell, Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals, Wiley-VCH, Weinheim, 2010.
3. Top 200 Pharmaceutical Products by Worldwide Sales in 2009, compiled and produced by the Njardarson Group (Cornell University): D. J. Mack, M. Brichacek, A. Plichta, J. T. Njardarson.
4. S. W. Pelletier, Alkaloids: Chemical and Biological Prospectives, Wiley, New York, 1983
5. D. Arora, H. Kumar, D. Malhotra, M. Malhotra, Pharmacologyonline 2011, 3, 659-668
6. N. Malecki, P. Carato, G. Rigo, J. F. Goossens, R. Houssin, C. Bailly, J. P. Henichart, Bioorg. Med. Chem. 2004, 12, 641-647.
7. P. Sohár, A. Csámpai, A. E. Szabõ, G. Stájer, J. Mol. Struct. 2004, 694, 139-147
8. U. A. Kshirsagar, N. P. Argade, Tetrahedron 2009, 65, 5244-5250.
9. D. J. Connolly, D. Cusack, T. P. O'Sullivan, P. J. Guiry, Tetrahedron 2005, 61, 10153-10202
10. L. He, H. Li, J. Chen, X.-F. Wu, RSC Adv. 2014, 4, 12065-12077; for selected examples on the synthesis of quinazolinediones, see
11. L. A. Shemchuk, V. P. Chernykh, O. S. Krys kiv, Russ. J. Org. Chem. 2006, 42, 382-387
12. M. Kurihara, J. Org. Chem. 1969, 34, 2123-2125
13. J. Khalafy, R. H. Prager, Aust. J. Chem. 1998, 51, 925-929
14. M. Mahdavi, R. Najafi, M. Saeedi, E. Alipour, A. Shafiee, A. Foroumadi, Helv. Chim. Acta 2013, 96, 419-423.
15. L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006
16. L. F. Tietze, Chem. Rev. 1996, 96, 115-136
17. E. Ruijter, R. Scheffelaar, R. V. A. Orru, Angew. Chem. 2011, 123, 6358-6371
18. Angew. Chem. Int. Ed. 2011, 50, 6234-6246
19. D. M. D Souza, T. J. J. Müller, Chem. Soc. Rev. 2007, 36, 1095-1108
20. B. Willy, T. J. J. Müller, Curr. Org. Chem. 2009, 13, 1777-1790
21. L. F. Tietze, A. Modi, Med. Res. Rev. 2000, 20, 304-322
22. J. E. Rixson, T. Chaloner, C. H. Heath, L. F. Tietze, S. G. Stewart, Eur. J. Org. Chem. 2012, 544-558
23. D. L. Priebbenow, S. G. Stewart, F. M. Pfeffer, Org. Biomol. Chem. 2011, 9, 1508-1515
24. D. L. Priebbenow, S. G. Stewart, F. M. Pfeffer, Tetrahedron Lett. 2012, 53, 1468-1471
25. C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51-80
26. E. Merkul, T. Oeser, T. J. J. Müller, Chem. Eur. J. 2009, 15, 5006-5011
27. A. V. Rotaru, I. D. Druta, T. Oeser, T. J. J. Müller, Helv. Chim. Acta 2005, 88, 1798-1812.
28. A. Schoenberg, I. Bartolet, R. F. Heck, J. Org. Chem. 1974, 39, 3318-3326
29. A. Schoenberg, R. F. Heck, J. Org. Chem. 1974, 39, 3327-3331
30. A. Brennführer, H. Neumann, M. Beller, Angew. Chem. 2009, 121, 4176-4196
31. Angew. Chem. Int. Ed. 2009, 48, 4114-4133
32. X.-F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev. 2011, 40, 4986-5009
33. X.-F. Wu, H. Neumann, M. Beller, Chem. Rev. 2013, 113, 1-35
34. X.-F. Wu, X. Fang, L. Wu, R. Jackstell, H. Neumann, M. Beller, Acc. Chem. Res. 2014, 47, 1041-1053.
35. X.-F. Wu, J. Schranck, H. Neumann, M. Beller, Chem. Eur. J. 2011, 17, 12246-12249
36. X.-F. Wu, B. Sundararaju, P. Anbarasan, H. Neumann, P. H. Dixneuf, M. Beller, Chem. Eur. J. 2011, 17, 8014-8017
37. H. Li, H. Neumann, M. Beller, X.-F. Wu, Angew. Chem. 2014, 126, 3247-3250
38. Angew. Chem. Int. Ed. 2014, 53, 3183-3186.
39. X. F. Wu, H. Neumann, M. Beller, Eur. J. Org. Chem. 2011, 4919-4924
40. X.-F. Wu, L. He, H. Neumann, M. Beller, Chem. Eur. J. 2013, 19, 12635-12638
41. X.-F. Wu, H. Neumann, S. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 13619-13623
42. X.-F. Wu, H. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 12595-12598
43. X.-F. Wu, H. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 12599-12602
44. X.-F. Wu, H. Neumann, S. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 8596-8599
45. J. Schranck, X.-F. Wu, H. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 4827-4831
46. X.-F. Wu, H. Neumann, M. Beller, Org. Biomol. Chem. 2011, 9, 8003-8005
47. H. Li, A. Spannenberg, H. Neumann, M. Beller, X.-F. Wu, Chem. Commun. 2014, 50, 2114-2116
48. H. Li, L. He, H. Neumann, M. Beller, X.-F. Wu, Green Chem. 2014, 16, 1336-1343
49. L. He, H. Li, H. Neumann, M. Beller, X.-F. Wu, Angew. Chem. 2014, 126, 1444-1448
50. Angew. Chem. Int. Ed. 2014, 53, 1420-1424.
51. R. É. Valter, R. B. Kampare, S. P. Valtere, D. É. Balode, A. É. Batse, Chem. Heterocycl. Compd. 1983, 19, 1290-1292.