Direct synthesis of quinazolines through copper-catalyzed reaction of aniline-derived benzamidines

Organic Letters

Volumn 12, Issue 17, 2010, Pages 3963-3965

  Ohta, Yusuke ^a   Tokimizu, Yusuke ^a   Oishi, Shinya ^a   Fujii, Nobutaka ^a   Ohno, Hiroaki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; ANILINE DERIVATIVE; BENZAMIDINE DERIVATIVE; COPPER; QUINAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

ANILINE COMPOUNDS; BENZAMIDINES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; CYCLIZATION; MOLECULAR STRUCTURE; QUINAZOLINES;

EID: 77956221924     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1016756     Document Type: Article

References (46)

1. Gundla, R.; Kazemi, R.; Sanam, R.; Muttineni, R.; Sarma, J. A. R. P.; Dayam, R.; Neamati, N. J. Med. Chem. 2008, 51, 3367
2. Mendes da Silva, J. F.; Walters, M.; Al-Damluji, S.; Ganellin, C. R. Bioorg. Med. Chem. 2008, 16, 7254
3. For recent reviews, see: Connolly, D. J.; Cusack, D.; O'Sullivan, T. P.; Guiry, P. J. Tetrahedron 2005, 61, 10153
4. Michael, J. P. Nat. Prod. Rep. 2007, 24, 223
5. For C-H alkynylation of heteroarenes in the presence of a stoichiometric amount of metal, see: Kalinin, V. K.; Pashchenko, D. N.; She, F. M. Mendeleev Commun. 1992, 2, 60
6. Trofimov, B. A.; Stepanova, Z. V.; Sobenina, L. N.; Mikhaleva, A. I.; Ushakov, I. A. Tetrahedron Lett. 2004, 45, 6513
7. Trofimov, B. A.; Sobenina, L. N.; Stepanova, Z. V.; Vakulskaya, T. I.; Kazheva, O. N.; Aleksandrov, G. G.; Dyachenko, O. A.; Mikhaleva, A. I. Tetrahedron 2008, 64, 5541 For a related radical reaction, see: Martelli, G.; Spagnolo, P.; Tiecco, M. J. Chem. Soc. B 1970, 1413
8. Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742 For other reactions of a highly reactive C-H bond on a heteroaryl ring, see: Gu, Y.; Wang, X. Tetrahedron Lett. 2009, 50, 763
9. Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 4156
10. Besseliévre, F.; Piguel, S. Angew. Chem., Int. Ed. 2009, 48, 9553
11. Kitahara, M.; Hirano, K.; Tsurugi, H.; Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 1772
12. Kobayashi, K.; Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2002, 124, 8528
13. Amemiya, R.; Fujii, M.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333
14. Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250
15. For dehydrogenative C-H alkynylation of activated arenes, see: de Haro, T.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 1512
16. Wei, Y.; Zhao, H.; Kan, J.; Su, W.; Hong, M. J. Am. Chem. Soc. 2010, 132, 2522
17. Yang, L.; Zhao, L.; Li, C.-J. Chem. Commun. 2010, 4184
18. For a recent review, see: Dudnik, A. S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2096
19. Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., Int. Ed. 2009, 48, 9346
20. For related C-H alkynylation of anilines, see refs 6b and 6c.
21. For selected examples of nitrogen alkynylation using alkynyliodonium salts, see: Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255
22. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440
23. Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426 For a reaction including 1,2-silyl migration, see: Witulski, B.; Stengel, T. Angew. Chem., Int. Ed 1998, 37, 489 For reviews, see: Zhdankin, V. V.; Stang, P. J. Tetrahedron 1998, 54, 10927
24. DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev 2010, DOI: 10.1021/cr100003s.
25. For a related arene-ynamide cyclization, see: Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slafer, B. W.; Davis, A. Org. Lett. 2005, 7, 1047 See also: Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572
26. Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932
27. Palladium-catalyzed quinazolin-2-one formation by rearrangement of benzo[ d ][1,3]oxazinamine derivatives
28. Costa, M.; Della Cá, N.; Gabriele, B.; Massera, C.; Salerno, G.; Soliani, M. J. Org. Chem. 2004, 69, 2469
29. Platinum-catalyzed quinazolin-2-one formation from alkoxy-substituted urea derivatives
30. Nakamura, I.; Sato, Y.; Terada, M. J. Am. Chem. Soc. 2009, 131, 4198
31. TfOH-mediated quinazolin-2-one formation
32. Wang, H.; Liu, L.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. Tetrahedron Lett. 2009, 50, 6841
33. Gold-catalyzed selective synthesis of quinazolin-2-ones over indoles
34. Gimeno, A.; Medio-Simon, M.; Ramírez de Arellano, C.; Asensio, G.; Cuenca, A. B. Org. Lett. 2010, 12, 1900
35. In this study, we focused on the reaction using copper salts (especially halides), generally cheaper than many other transition-metal salts/complexes including those of palladium, nickel, and gallium.
36. For synthesis of related 1-alkynylbenziodoxoles, see: Ochiai, M.; Masaki, Y.; Shiro, M. J. Org. Chem. 1991, 56, 5511
37. Zhdankin, V. V.; Kuehl, C. J.; Krasutsky, A. P.; Bolz, J. T.; Simonsen, A. J. J. Org. Chem. 1996, 61, 6547 For a related reaction, see: Nicolai, S.; Erard, S.; Fernández González, D.; Waser, J. Org. Lett. 2010, 12, 384
38. Fernández González, D.; Brand, J. P.; Waser, J. Chem.-Eur. J. 2010, DOI: chem.201001539.
39. The reaction conditions including solvent, base, and catalyst loading were not optimized with 2i.
40. Anderson, R. K.; Carter, S. D.; Cheeseman, G. W. H. Tetrahedron 1979, 35, 2463
41. For related electrophilic reactions with iodoxolane reagents, see: Eisenberger, P.; Gischig, S.; Togni, A. Chem.-Eur. J. 2006, 12, 2579
42. Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem., Int. Ed. 2007, 46, 754
43. Eisenberger, P.; Kieltsch, I.; Armanino, N.; Togni, A. Chem. Commun. 2008, 1575
44. Stanek, K.; Koller, R.; Togni, A. J. Org. Chem. 2008, 73, 7678
45. Koller, R.; Stanek, K.; Stolz, D.; Aardoom, R.; Niedermann, K.; Togni, A. Angew. Chem., Int. Ed. 2009, 48, 4332
46. Niedermann, K.; Welch, J. M.; Koller, R.; Cvengroŝ, J.; Santschi, N.; Battaglia, P.; Togni, A. Tetrahedron 2010, 66, 5753 See also: Zhdankin, V. V.; Kuehl, C. J.; Krasutsky, A. P.; Bolz, J. T.; Mismash, B.; Woodward, J. K.; Simonsen, A. J. Tetrahedron Lett. 1995, 36, 7975