Direct synthesis of 2-aryl-1,3-benzoselenazoles by reaction of bis(2-aminophenyl) diselenides with aryl aldehydes using sodium metabisulfite

Tetrahedron

Volumn 69, Issue 4, 2013, Pages 1316-1321

  Radatz, Cátia Schwartz ^a   Alves, Diego ^b   Schneider, Paulo Henrique ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

Author keywords

1,3 Benzoselenazoles; Aldehydes; Diselenides; Heterocycles; Reducing agent

Indexed keywords

1,3 BENZOSELENAZOLE DERIVATIVE; ALDEHYDE DERIVATIVE; BIS(2 AMINOPHENYL)DISELENIDE DERIVATIVE; DIMETHYL SULFOXIDE; DIPHENYL DISELENIDE; REDUCING AGENT; SELENAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MICROWAVE IRRADIATION; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 84871997160     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.11.091     Document Type: Article

References (113)

1. E. Oksuzoglu, B. Tekiner-Gulbas, S. Alper, O. Temiz-Arpaci, I. Ertan, T. Yildiz, N. Diril, E. Sener-Aki, and I. Yalcin J. Enzyme Inhib. Med. Chem. 23 2008 37
2. M.L. McKee, and S.M. Kerwin Bioorg. Med. Chem. 16 2008 1775
3. D. Kumar, M.R. Jacob, M.B. Reynolds, and S.M. Kerwin Bioorg. Med. Chem. 10 2002 3997
4. S.-T. Huang, I.-J. Hsei, and C. Chen Bioorg. Med. Chem. 14 2006 6106
5. L.-Q. Sun, J. Chen, M. Bruce, J.A. Deskus, J.R. Epperson, K. Takaki, G. Johnson, L. Iben, C.D. Mahle, E. Ryan, and C. Xu Bioorg. Med. Chem. Lett. 14 2004 3799
6. C.K. Lai, H.C. Liu, F.J. Li, K.L. Cheng, and H.S. Sheu Liq. Cryst. 32 2005 85
7. A. Tavares, P.H. Schneider, and A.A. Merlo Eur. J. Org. Chem. 2009 889
8. J.A. Passo, G.D. Vilela, P.H. Schneider, O.M.S. Ritter, and A.A. Merlo Liq. Cryst. 35 2008 833
9. X. Zhang, H. Gorohmaru, M. Kadowaki, T. Kobayashi, T. Ishi-I, T. Thiemann, and S. Mataka J. Mater. Chem. 14 2004 1901
10. F.S. Santos, T.M.H. Costa, V. Stefani, P.F.B. Gonçalves, R.R. Descalzo, E.V. Benvenutti, and F.S. Rodembusch J. Phys. Chem. A 115 2011 13390
11. S.P.G. Costa, G. Ferreira, J.A. Kirsch, and A.M.F. Oliveira-Campos J. Chem. Res. 1997 314
12. K. Oketani, T. Inoue, and M. Murakami Eur. J. Pharmacol. 427 2001 159
13. I. Hutchinson, M.-S. Chua, H.L. Browne, V. Trapani, T.D. Bradshaw, A.D. Westwell, and M.F.C. Stevens J. Med. Chem. 44 2001 1446
14. T.D. Bradshaw, M.F.G. Stevens, and A.D. Westwell Curr. Med. Chem. 8 2001 203
15. T. Mouri, J. Tokumura, S. Kochi, H. Fukui, J. Nakano, T. Ando, and M. Hori J. Pestic. Sci. 27 2002 353
16. A. Heynderickx, R. Guglielmetti, R. Dubest, J. Aubard, and A. Samat Synthesis 2003 1112
17. C.A. Mathis, Y. Wang, D.P. Holt, G.-F. Huang, M.L. Debnath, and W.E. Klunk J. Med. Chem. 46 2003 2740
18. T.D. Bradshaw, and A.D. Westwell Curr. Med. Chem. 11 2004 1009
19. C.G. Mortimer, G. Wells, J.-P. Crochard, E.L. Stone, T.D. Bradshaw, M.F.G. Stevens, and A.D. Westwell J. Med. Chem. 49 2006 179
20. E. Brantley, S. Antony, G. Kohlhagen, L.-H. Meng, K. Agama, S.F. Stinton, E.A. Sausville, and Y. Pommier Cancer Chemother. Pharmacol. 58 2006 62
21. M. Alamgir, D.S.C. Black, and N. Kumar Synthesis, Reactivity and Biological Activity of Benzimidazoles in Topics in Heterocyclic Chemistry Vol. 9 2007 Springer Berlin p 87 and references therein
22. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893
23. H. Yoshida, R. Nakao, H. Nohta, and M. Yamaguchi Dyes Pigm. 47 2000 239
24. A. Rao, A. Chimirri, E. De Clercq, A.M. Monforte, P. Monforte, C. Pannecouque, and M. Zappala II Farmaco 57 2002 819
25. D.J. Skalitzky, J.T. Marakovits, K.A. Maegley, A. Ekker, X.-H. Yu, Z. Hostomsky, S.E. Webber, B.W. Eastman, R. Almassy, J. Li, N.J. Curtin, D.R. Newell, A.H. Calvert, R.J. Griffin, and B.T. Golding J. Med. Chem. 46 2003 210
26. M. Wang, M. Gao, B.H. Mock, K.D. Miller, G.W. Sledge, G.D. Hutchins, and Q.-H. Zheng Bioorg. Med. Chem. 14 2006 8599
27. G.O.W. Lins, L.F. Campo, F.S. Rodembusch, and V. Stefani Dyes Pigm. 84 2010 114
28. Q. Sun, R. Wu, S. Cai, Y. Lin, L. Sellers, K. Sakamoto, B. He, and B.R. Peterson J. Med. Chem. 54 2011 1126
29. I. Hutchinson, S.A. Jenninga, B.R. Vishnuvajjala, A.D. Westwell, and M.F.G. Stevens J. Med. Chem. 45 2002 744
30. R. Caujolle, P. Loiseau, M. Payard, P. Gayral, and M.N. Kerhir Ann. Pharm. Fr. 47 1989 68
31. K. Yamamoto, M. Fujita, K. Tabashi, Y. Kawashima, E. Kato, M. Oya, T. Iso, and J. Iwao J. Med. Chem. 31 1988 919
32. I. Petkov, T. Deligeorgiev, P. Markov, M. Evstatiev, and S. Fakirov Polym. Degrad. Stab. 33 1991 53
33. R.C. Santos, N.V.S. Faleiro, L.F. Campo, M.L. Scroferneker, V.A. Corbellini, F.S. Rodembusch, and V. Stefani Tetrahedron Lett. 52 2011 3048
34. S.R. Grando, C.M. Pessoa, M.R. Gallas, T.M.H. Costa, F.S. Rodembusch, and E.V. Benvenutti Langmuir 25 2009 13219
35. F.S. Rodembusch, F.P. Leusin, L.F. Campo, and V. Stefani J. Lumin. 126 2007 728
36. H. Hioki, K. Matsushita, M. Kubo, K. Harada, M. Kodama, and Y. Fukuyama Tetrahedron 63 2007 11315
37. X. Fei, S. Yang, B. Zhang, Z. Liu, and Y. Gu J. Comb. Chem. 9 2007 943
38. J. Hyvl, and J. Srogl Eur. J. Org. Chem. 2010 2849
39. C. Zhu, and T. Akiyama Synlett 2010 2457
40. A. Stella, K. Segers, S. De Jonghe, B. Vanderhoydonck, J. Rozenski, J. Anne, and P. Herdewijn Chem. Biodiversity 8 2011 253
41. L. Ouyang, Y. Huang, Y. Zhao, G. He, Y. Xie, J. Liu, J. He, B. Liu, and Y. Wei Bioorg. Med. Chem. Lett. 22 2012 3044
42. X.-H. Shi, Z. Wang, Y. Xia, T.-H. Ye, M. Deng, Y.-Z. Xu, Y.-Q. Wei, and L.-T. Yu Molecules 17 2012 3933
43. M.T. Bogert, and A. Stull J. Am. Chem. Soc. 49 1927 2011
44. C. Hasan, and R.F. Hunter J. Chem. Soc. 1935 1762
45. S. Fujiwara, Y. Asanuma, T. Shinike, and N. Kambe J. Org. Chem. 72 2007 8087
46. M. Kaname, M. Minoura, and H. Sashida Tetrahedron Lett. 52 2011 505
47. K. Kobayashi, and Y. Yokoi Helv. Chim. Acta 95 2012 761
48. M.J. Parnham, and E. Graf Prog. Drug. Res. 36 1991 9
49. G. Mugesh, W.W. du Mont, and H. Sies Chem. Rev. 101 2001 2125
50. C.W. Nogueira, G. Zeni, and J.B.T. Rocha Chem. Rev. 104 2004 6255
51. E.E. Alberto, V. Nascimento, and A.L. Braga J. Braz. Chem. Soc. 21 2010 2032
52. C.W. Nogueira, and J.B.T. Rocha J. Braz. Chem. Soc. 21 2010 2055
53. C.W. Nogueira, and J.B.T. Rocha Arch. Toxicol. 85 2011 1313
54. K.D. Volkova, V.B. Kovalska, M.Y. Losytskyy, A. Bento, L.V. Reis, P.F. Santos, P. Almeida, and S.M. Yarmoluk J. Fluoresc. 18 2008 877
55. P.F. Santos, L.V. Reis, P. Almeida, and D.E. Lynch CrystEngComm 13 2011 1333
56. N.R. Conley, A. Dragulescu-Andrasi, J. Rao, and W.E. Moerner Angew. Chem., Int. Ed. 51 2012 1
57. H.S. Kim, Y.J. Kim, H. Lee, K.Y. Park, C. Lee, and C.S. Chin Angew. Chem., Int. Ed. 41 2002 4300
58. E.J. Lenardão, S. Feijó, J.O. Thurow, G. Perin, R.G. Jacob, and C.C. Silveira Tetrahedron Lett. 50 2009 5215
59. E.J. Lenardão, E.L. Borges, S.R. Mendes, G. Perin, and R.G. Jacob Tetrahedron Lett. 49 2008 1919
60. E.J. Lenardão, S.R. Mendes, P.C. Ferreira, G. Perin, C.C. Silveira, and R.G. Jacob Tetrahedron Lett. 47 2006 7439
61. S. Thurow, V.A. Pereira, D.M. Martinez, D. Alves, G. Perin, R.G. Jacob, and E.J. Lenardão Tetrahedron Lett. 52 2011 640
62. E.E. Alberto, L.L. Rossato, S.H. Alves, D. Alves, and A.L. Braga Org. Biomol. Chem. 9 2011 1001
63. A.L. Braga, O.E.D. Rodrigues, M.W. Paixão, H.R. Appelt, C.C. Silveira, and D.P. Bottega Synthesis 2002 2338
64. A.L. Braga, M.W. Paixão, D.S. Ludtke, C.C. Silveira, and O.E.D. Rodrigues Org. Lett. 5 2003 2635
65. R.S. Rambo, and P.H. Schneider Tetrahedron: Asymmetry 21 2010 2254
66. A.L. Braga, F. Vargas, J.A. Sehnem, and R.C. Braga J. Org. Chem. 70 2005 9021
67. A.L. Braga, M.W. Paixão, and G. Marin Synlett 2005 1975
68. D.M. Freudendahl, S.A. Shahzad, and T. Wirth Eur. J. Org. Chem. 2009 1649
69. M. Godoi, M.W. Paixão, and A.L. Braga Dalton Trans. 40 2011 11347
70. H. Maeda, N. Kambe, N. Sonoda, S. Fujiwara, and T. Shin-ike Tetrahedron 53 1997 13667
71. P.-F. Zhang, and Z.-C. Chen Synthesis 2000 1219
72. K. Geisler, W.-D. Pfeiffer, C. Müller, E. Nobst, E. Bulka, and P. Langer Synthesis 2003 1215
73. K. Geisler, A. Künzler, H. Below, E. Bulka, W.-D. Pfeiffer, and P. Langer Synlett 2003 1195
74. K. Geisler, W.-D. Pfeiffer, A. Künzler, H. Below, E. Bulka, and P. Langer Synthesis 2004 875
75. K. Geisler, A. Künzler, H. Below, E. Bulka, W.-D. Pfeiffer, and P. Langer Synthesis 2004 97
76. H. Below, W.-D. Pfeiffer, K. Geisler, M. Lalk, and P. Langer Eur. J. Org. Chem. 2005 3637
77. M. Koketsu, K. Kanoh, H. Ando, and H. Ishihara Heteroat. Chem. 17 2006 88
78. M. Narender, M.S. Reddy, V.P. Kumar, V.P. Reddy, Y.V.D. Nageswar, and K.R. Rao J. Org. Chem. 72 2007 1849
79. H. Li, W.H. Hallows, J.S. Punzi, V.E. Marquez, H.L. Carrell, K.W. Pankiewicz, K.A. Watanabe, and B.M. Goldstein Biochemistry 33 1994 23
80. M. Koketsu, S.Y. Choi, H. Ishihara, B.O. Lim, H. Kim, and S.Y. Kim Chem. Pharm. Bull. 50 2002 1594
81. A. Sekiguchi, A. Nishina, H. Kimura, R. Fukumoto, K. Kanoh, H. Ishihara, and M. Koketsu Chem. Pharm. Bull. 53 2005 1439
82. P.F. Santos, L.V. Reis, P. Almeida, J.P. Serrano, A.S. Oliveira, and L.F.V. Ferreira J. Photochem. Photobiol., A 163 2004 267
83. P.F. Santos, L.V. Reis, P. Almeida, A.S. Oliveira, and L.F.V. Ferreira J. Photochem. Photobiol., A 160 2003 159
84. L.V. Reis, J.P.C. Serrano, P. Almeida, and P.F. Santos Synlett 2002 1617
85. A.A. Weekes, M.C. Bagley, and A.D. Westwell Tetrahedron 67 2011 7743
86. Z. Wang, R. Tang, and J. Li Chin. J. Chem. 29 2011 314
87. H. Deng, Z. Li, F. Ke, and X. Zhou Chem. - Eur. J. 18 2012 4880
88. E.G. Janzen J. Phys. Chem. 76 1972 157
89. H.F. Ridley, R.G.W. Spickett, and G.M. Timmis J. Heterocycl. Chem. 2 1965 453
90. R.L. Lombardy, F.A. Tanious, K. Ramachandran, R.R. Tidwell, and W.D. Wilson J. Med. Chem. 39 1996 1452
91. H. Göker, C. Ku, D.W. Boykin, S. Yildiz, and N. Altanar Bioorg. Med. Chem. 10 2002 2589
92. S. Özden, D. Atabey, S. Yildiz, and H. Göker Bioorg. Med. Chem. 13 2005 1587
93. A.K.S. Chauhan, S.N. Bharti, R.C. Srivastava, R.J. Butcher, and A. Duthie J. Organomet. Chem. 75 2012 708
94. D.S. Rampon, F.S. Rodembusch, P.F.B. Gonçalves, R.V. Lourega, A.A. Merlo, and P.H. Schneider J. Braz. Chem. Soc. 21 2010 2100
95. D.S. Rampon, F.S. Rodembusch, J.M.F.M. Schneider, I.H. Bechtold, P.F.B. Gonçalves, A.A. Merlo, and P.H. Schneider J. Mater. Chem. 20 2010 715
96. D.S. Rampon, R. Giovenardi, T.L. Silva, R.S. Rambo, A.A. Merlo, and P.H. Schneider Eur. J. Org. Chem. 2011 7066
97. N.F. Pavin, F. Donato, F.W.S. Cibin, C.R. Jesse, P.H. Schneider, H.D. Salles, L.A. Soares, D. Alves, and L. Savegnago Eur. J. Pharmacol. 668 2011 169
98. C.S. Freitas, A.M. Barcellos, V.G. Ricordi, J.M. Pena, G. Perin, R.G. Jacob, E.J. Lenardão, and D. Alves Green Chem. 13 2011 2931
99. F.M. Libero, M.C.D. Xavier, F.N. Victoria, P.S. Nascente, L. Savegnago, G. Perin, and D. Alves Tetrahedron Lett. 53 2012 3091
100. V.G. Ricordi, C.S. Freitas, G. Perin, E.J. Lenardão, R.G. Jacob, L. Savegnago, and D. Alves Green Chem. 14 2012 1030
101. A.M. Deobald, L.R.S. Camargo, G. Tabarelli, M. Hörner, O.E.D. Rodrigues, D. Alves, and A.L. Braga Tetrahedron Lett. 51 2010 3364
102. P. Lidström, and J.P. Tierney Microwave-assisted Organic Synthesis 2005 Blackwell Oxford
103. A. Loupy Microwaves in Organic Synthesis 2nd ed. 2006 Wiley-VCH Weinheim
104. C.O. Kappe, D. Dallinger, and S.S. Murphree Practical Microwave Synthesis for Organic Chemists: Strategies, Instruments, and Protocols 2009 Wiley-VCH Weinheim
105. A. de la Hoz, A. Diaz-Ortis, A. Moreno, and F. Langa Eur. J. Org. Chem. 2000 3659
106. P. Lidström, J.P. Tierney, B. Wathey, and J. Westman Tetrahedron 57 2001 9225
107. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250
108. C.E. Leadbeater Chem. Commun. 2005 2881
109. B.A. Roberts, and C.R. Strauss Acc. Chem. Res. 38 2005 653
110. M.C. Bagley, and M.C. Lubinu Top. Heterocycl. Chem. 1 2006 31
111. S. Caddick, and R. Fitzmaurice Tetrahedron 65 2009 3325
112. P. Appukkuttan, V.P. Mehta, and E. Van der Eycken Chem. Soc. Rev. 39 2010 1467
113. W.L.F. Armarego, and D.D. Perrin Purification of Laboratory Chemicals 4th ed. 1996 Elsevier