Oxidative dehydrogenative couplings of pyrazol-5-amines selectively forming azopyrroles

Journal of Organic Chemistry

Volumn 79, Issue 9, 2014, Pages 4018-4024

  Jiang, Bo ^a   Ning, Yi ^a   Fan, Wei ^a   Tu, Shu Jiang ^a   Li, Guigen ^b,c  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

^c TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES;

AZO COMPOUND; DEHYDROGENATIVE COUPLING; OXIDATIVE COUPLINGS; SELECTIVE SYNTHESIS; SONOGASHIRA CROSS-COUPLING; TERMINAL ALKYNE;

COUPLINGS;

ALKYNE; AZO COMPOUND; AZOPYRROLE DERIVATIVE; CARBON; COPPER; FUNCTIONAL GROUP; IODINE; NITROGEN; PHENANTHROLINE; PYRAZOL 5 AMINE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; AMINE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CROSS COUPLING REACTION; IODINATION; OXIDATION; OXIDATIVE COUPLING; OXIDATIVE DEHYDROGENATION; SONOGASHIRA REACTION; SUBSTITUTION REACTION; SYNTHESIS; CHEMISTRY; HYDROGENATION; OXIDATION REDUCTION REACTION;

AMINES; AZO COMPOUNDS; HYDROGENATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRAZOLES;

EID: 84899844998     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5004967     Document Type: Article

References (51)

1. Hunger, K. Industrial Dyes: Chemistry, Properties, Applications; Wiley-VCH: Weinheim, 2003.
2. Anderson, R. G.; Nickless, G. Analyst 1967, 92, 207
3. Ashutosh, P. N. D.; Mehrotra, J. K. Colourage 1979, 26, 25
4. Athey, R. D., Jr. Eur. Coatings J. 1998, 3, 146
5. Sheppard, C. S. Encycl. Polym. Sci. Eng. 1985, 2, 143
6. Hoult, J. R. S. Drugs 1986, 32, 18
7. Sandborn, W. J. Am. J. Gastroenterol. 2002, 97, 2939
8. Cation, S. C.; Farris, E. Concise Encyclopedia of Chemical Technology; Wiley: New York, 1985.
9. Cisnetti, F.; Ballardini, R.; Credi, A.; Gandolfi, M. T.; Masiero, S.; Negri, F.; Pieraccini, S.; Spada, G. P. Chem.-Eur. J. 2004, 10, 2011
10. Bandara, D.; Burdette, C. S. Chem. Soc. Rev. 2012, 41, 1809
11. Ikeda, T.; Tsutsumi, O. Science 1995, 268, 1873
12. Tamaoki, N. Adv. Mater. 2001, 13, 1135
13. Beharry, A. A.; Wong, L.; Tropepe, V.; Woolley, G. A. Angew. Chem., Int. Ed. 2011, 50, 1325
14. Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kutinake, M.; Nakashima, N. J. Am. Chem. Soc. 1997, 119, 7605
15. Grirrane, A.; Corma, A.; Garca, H. Science 2008, 322, 1661
16. Corma, A.; Concepcin, P.; Serna, P. Angew. Chem. 2007, 119, 7404
17. Angew. Chem., Int. Ed. 2007, 46, 7266.
18. Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 1326
19. Lim, Y.-K.; Lee, K.-S.; Cho, C.-G. Org. Lett. 2003, 5, 979
20. Drug, E.; Gozin, M. J. Am. Chem. Soc. 2007, 129, 13784
21. Baumgarten, H. E.; Staklis, A.; Miller, E. M. J. Org. Chem. 1965, 30, 1203
22. Firouzabadi, H.; Mostafavippor, Z. Bull. Chem. Soc. Jpn. 1983, 56, 914
23. Birchall, J. M.; Haszeldine, R. N.; Kemp, J. E. G. Chem. Commun. 1970, 449
24. Wenkert, K.; Wickberg, B. J. Am. Chem. Soc. 1962, 84, 4914
25. Farhadi, S.; Zaringhadam, P.; Sahamieh, R. Z. Acta Chim. Slov. 2007, 54, 647
26. Goldstein, S. L.; McNelis, E. J. Org. Chem. 1973, 38, 183
27. Huang, H.; Sommerfeld, D.; Dunn, B. C.; Lloyd, C. R.; Eyring, E. M. J. Chem. Soc., Dalton Trans. 2001, 1301
28. Kumar, A.; Bhattacharjee, G. J. Indian Chem. Soc. 1991, 68, 523
29. Wang, M. X.; Funabiki, K.; Matsui, M. Dyes Pigments 2003, 57, 77
30. Dabbagh, H. A.; Teimouri, A.; Chermahini, A. N. Dyes Pigments 2007, 73, 239
31. Salaheldin, A. M.; Oliveira-Campos, A. M. F.; Rodrigues, L. M. Tetrahedron Lett. 2007, 48, 8819
32. Hill, J. G.; Rossiter, B. E.; Sharpless, K. B. J. Org. Chem. 1983, 48, 3607
33. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810
34. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 56
35. Zhang, J.; Zhu, D.; Yu, C.; Wan, C.; Wang, Z. Org. Lett. 2010, 12, 2841
36. Wan, C.; Gao, L.; Wang, Q.; Zhang, J.; Wang, Z. Org. Lett. 2010, 12, 3902
37. Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, K. R. Org. Lett. 2013, 15, 1092
38. Frota, C.; Casagrande, G. A.; Pizzuti, L.; Raminelli, C. Curr. Org. Synth. 2013, 10, 265
39. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874
40. Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566
41. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 1998.
42. Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002.
43. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 2004.
44. For the preparation of 4-iodopyrazoles, see: Kim, M. M.; Ruck, R. T.; Zhao, D.; Huffman, M. A. Tetrahedron Lett. 2008, 49, 4026
45. Hub, W.; Schneider, S.; Doerr, F.; Oxman, J. D.; Lewis, F. D. J. Am. Chem. Soc. 1984, 106, 701
46. Scaiano, J. C.; Garca, S.; Garca, H. Tetrahedron Lett. 1997, 38, 5929
47. Brede, O.; Maroz, A.; Hermann, R.; Naumov, S. J. Phys. Chem. A 2005, 109, 8081
48. Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2010, 49, 6174
49. Gogoi, A.; Guin, S.; Rout, S. K.; Patel, B. K. Org. Lett. 2013, 15, 1802
50. Xia, X.-F.; Zhang, L.-L.; Song, X.-R.; Niu, Y.-N.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2013, 1410
51. Cheng, K.; Huang, L.; Zhang, Y. Org. Lett. 2009, 11, 2908