A solvent- and metal-free synthesis of 3-chacogenyl-indoles employing DMSO/I2 as an eco-friendly catalytic oxidation system

Journal of Organic Chemistry

Volumn 79, Issue 9, 2014, Pages 4125-4130

  Azeredo, Juliano B ^a   Godoi, Marcelo ^a   Martins, Guilherme M ^b   Silveira, Claudio C ^b   Braga, Antonio L ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^b FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC OXIDATION;

DICHALCOGENIDES; ECO-FRIENDLY; METAL-FREE SYNTHESIS; MOLECULAR IODINE;

ENVIRONMENTAL PROTECTION;

3 CHACOGENYLINDOLE; CHALCOGEN; DIMETHYL SULFOXIDE; INDOLE DERIVATIVE; IODINE; METAL; OXIDIZING AGENT; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; DRUG STRUCTURE; DRUG SYNTHESIS; GREEN CHEMISTRY; MICROWAVE IRRADIATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION OPTIMIZATION; REACTION TIME; TEMPERATURE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATALYSIS; DIMETHYL SULFOXIDE; INDOLES; IODINE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SOLVENTS;

EID: 84899801004     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5000779     Document Type: Article

References (65)

1. Sundberg, R. J. Indoles; Academic Press: New York, 1997.
2. Joule, J. A. Indole and its Derivatives in Science of Synthesis: Howben-Weyl Methods of Molecular Transformations; Thomas, E. J., Ed.; George Thieme: Stuttgart, 2001; Vol. 10, Chapter 10.13.
3. Saxton, J. E. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998.
4. Bandini, M.; Eichholzer, A. Angew. Chem, Int. Ed. 2009, 48, 9608-9644
5. La Regina, G.; Gatti, V.; Famiglini, V.; Piscitelli, F.; Silvestri, R. ACS Comb. Sci. 2012, 14, 258-262
6. Zhou, N.; Zeller, W.; Krohn, M.; Anderson, H.; Zhang, J.; Onua, E.; Kiselyov, A. S.; Ramirez, J.; Halldorsdottir, G.; Andrésson, P.; Gurney, M. E.; Singh, J. Bioorg. Med. Chem. Lett. 2009, 19, 123-126
7. La Regina, G.; Bai, R.; Rensen, W. M.; Di Cesare, E.; Coluccia, A.; Piscitelli, F.; Famiglini, V.; Regio, A.; Nalli, M.; Pelliccia, S.; Da Pozzo, E.; Costa, B.; Granata, I.; Porta, A.; Maresca, B.; Soriani, A.; Iannitto, M. L.; Santoni, A.; Li, J.; Cona, M. M.; Chen, F.; Ni, Y.; Brancale, A.; Dondio, G.; Vultaggio, S.; Varasi, M.; Mercurio, C.; Martini, C.; Hamel, E.; Lavia, P.; Novellino, E.; Silvestri, R. J. Med. Chem. 2013, 56, 123-149
8. Cianchi, F.; Cortesini, C.; Magnelli, L.; Fanti, E.; Papucci, L.; Schiavone, N.; Messerini, L.; Vannacci, A.; Capaccioli, S.; Perna, F.; Lulli, M.; Fabbroni, V.; Perigli, G.; Bechi, P.; Masini, E. Mol. Cancer Ther. 2006, 5, 2716-2726
9. Nuth, M.; Guan, H.; Zhukovskaya, N.; Saw, Y. L.; Ricciardi, R. P. J. Med. Chem. 2013, 56, 3235-3246
10. Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Chem. Rev. 2004, 104, 6255-6285
11. Alberto, E. E.; Nascimento, V.; Braga, A. L. J. Braz. Chem. Soc. 2010, 21, 2032-2041
12. Nogueira, C. W.; Rocha, J. B. T. J. Braz. Chem. Soc. 2010, 21, 2055-2071
13. Nascimento, V.; Alberto, E. E.; Tondo, D. W.; Dambrowski, D.; Detty, M. R.; Nome, F.; Braga, A. L. J. Am. Chem. Soc. 2012, 134, 138-141
14. Sarma, B. K.; Mugesh, G. J. Am. Chem. Soc. 2005, 127, 11477-11485
15. Roy, G.; Nethaji, M.; Mugesh, G. J. Am. Chem. Soc. 2004, 126, 2712-2713
16. Back, T. G. Organoselenium Chemistry-A Practical Approach; Oxford University Press: Oxford, U.K., 1999.
17. Guo, Y. J.; Tang, R. Y.; Li, J. H.; Zhong, P.; Zhang, X. G. Adv. Synth. Catal. 2009, 351, 2615-2618
18. Sanz, R.; Guilarte, V.; Castroviejo, M. P. Synlett 2008, 3006-3010
19. Barraja, P.; Diana, P.; Carbone, A.; Cirrincione, G. Tetrahedron 2008, 64, 11625-11631
20. Baig, N. B. R.; Chandrakala, R. N.; Sudhir, V. S.; Chandrasekaran, S. J. Org. Chem. 2010, 75, 2910-2921
21. Yadav, J. S.; Subba Reddy, B. V.; Jayasudhan Reddy, Y. Tetrahedron Lett. 2007, 48, 7034-7037
22. Yadav, J. S.; Subba Reddy, B. V.; Reddy, Y. J.; Praneeth, K. Synthesis 2009, 1520-1524
23. Li, Z.; Hong, J. Q.; Zhou, X. J. Tetrahedron 2011, 67, 3690-3697
24. Ge, W.; Wei, Y. Synthesis 2012, 44, 934-940
25. Maeda, Y.; Koyabu, M.; Nishimuraand, T.; Uemura, S. J. Org. Chem. 2004, 69, 7688-7693
26. Tudge, M.; Tamiya, M.; Savarin, C.; Humphrey, G. R. Org. Lett. 2006, 8, 565-568
27. Matsugi, M.; Murata, K.; Gotanda, K.; Nambu, H.; Anilkumar, G.; Matsumoto, K.; Kita, Y. J. Org. Chem. 2001, 66, 2434-2441
28. Silveira, C. C.; Mendes, S. R.; Wolf, L.; Martins, G. M. Tetrahedron Lett. 2010, 51, 2014-2016
29. Zhao, X.; Yu, Z.; Xu, T.; Wu, P.; Yu, H. Y. Org. Lett. 2007, 9, 5263-5266
30. Marcantoni, E.; Cipolletti, R.; Marsili, L.; Menichetti, S.; Properzi, R.; Viglianisi, C. Eur. J. Org. Chem. 2013, 132-140
31. Yang, F. L.; Tian, S. K. Angew. Chem., Int. Ed. 2013, 52, 4929-4932
32. Wu, Q.; Zhao, D.; Qin, X.; Lan, J.; You, J. Chem. Commun. 2011, 47, 9188-9190
33. Chen, Y.; Cho, C.; Shi, F.; Larock, R. C. J. Org. Chem. 2009, 74, 6802-6811
34. Chen, Y.; C. Cho, C.; Larock, R. C. Org. Lett. 2009, 11, 173-176
35. Li, Z.; Hong, L.; Liu, R.; Shen, J.; Zhou, X. Tetrahedron Lett. 2011, 52, 1343-1347
36. Sperança, A.; Godoi, B.; Menezes, P. H.; Zeni, G. Synlett 2013, 24, 1125-1132
37. Liu, J.; Li, P.; Chen, W.; Wang, L. Chem. Commun. 2012, 48, 10052-10054
38. Zimmermann, E.; Thurow, S.; Freitas, C.; Mendes, S. R.; Perin, G.; Alves, D.; Jacob, R.; Lenardão, E. J. Molecules 2013, 18, 4081-4090
39. Silveira, C. C.; Mendes, S. R.; Wolf, L.; Martins, G. M.; von Mühlen, L. Tetrahedron 2012, 68, 10464-10469
40. Ge, Y.; Wei, Y. Green Chem. 2012, 14, 2066-2070
41. Xiao, F.; Xie, H.; Liu, S.; Deng, G. J. Adv. Synth. Catal. 2014, 356, 364-368
42. Ju, Y.; Kumar, D.; Varma, R. S. J. Org. Chem. 2006, 71, 6697-6700
43. Wu, Q.; Zhao, D.; Qin, X.; Lan, J.; You, J. Chem. Commun. 2011, 47, 9188-9190
44. Görmer, K.; Waldmann, H.; Triola, G. J. Org. Chem. 2010, 75, 1811-1813
45. Botteselle, G. V.; Godoi, M.; Galetto, F. Z.; Bettanin, L.; Singh, D.; Rodrigues, O. E. D.; Braga, A. L. J. Mol. Catal. A 2012, 365, 186-193
46. Azeredo, J. B.; Godoi, M.; Schwab, R. S.; Botteselle, G. V.; Braga, A. L. Eur. J. Org. Chem. 2013, 5188-5194
47. Herrero, M. A.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2008, 73, 36-47
48. Strauss, C. R.; Rooney, D. W. Green Chem. 2010, 12, 1340-1345
49. Najeebullah, M.; Knight, D. W.; Munawar, M. A.; Yaseenx, A.; Vincenzo, F. Tetrahedron 2010, 66, 6761-6764
50. Barros, M. T.; Petrova, K. T.; Correia-da-Silva, P.; Potewar, T. M. Green Chem. 2011, 13, 1897-1906
51. Nadagouda, M. N.; Speth, T. F.; Varma, R. S. Acc. Chem. Res. 2011, 44, 469-478
52. Braga, A. L.; Paixão, M. W.; Westermann, B.; Schneider, P. H.; Wessjohann, L. A. J. Org. Chem. 2008, 73, 2879-2882
53. Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563-2591
54. Obermayer, D.; Gutmann, B.; Kappe, C. O. Angew. Chem., Int. Ed. 2009, 48, 8321-8324
55. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283
56. Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250-6284
57. Varma, R. S. Green Chem. 1999, 1, 43-55
58. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025-1074
59. Godoi, M.; Ricardo, E. W.; Botteselle, G. V.; Galetto, F. Z.; Azeredo, J. B.; Braga, A. L. Green Chem. 2012, 14, 456-460
60. Perin, G.; Jacob, R. G.; Dutra, L. G.; Azambuja, F.; Santos, G. F. F.; Lenardão, E. J. Tetrahedron Lett. 2006, 47, 935-938
61. Perin, G.; Mendes, S. R.; Silva, M. S.; Lenardão, E. J.; Jacob, R. G.; Santos, P. C. Synth. Commun. 2006, 36, 2587-2595
62. Ananikov, V. P.; Gayduk, K. A.; Beletskaya, I. P.; Khrustalev, V. N.; Antipin, M. Y. Chem.-Eur. J. 2008, 14, 2420-2434
63. Hiller, F. W.; Krueger, J. H. Inorg. Chem. 1967, 6, 528-533
64. Tamres, M.; Bhat, S. N. J. Am. Chem. Soc. 1972, 94, 2577-2578
65. Lo, S. J.; Tamres, M. Can. J. Chem. 1983, 61, 1933-1940 Nível Superior