New heteroaromatic azo compounds based on pyridine, isoxazole, and benzothiazole for efficient and highly selective amidation and mono-N-benzylation of amines under Mitsunobu conditions

Bulletin of the Chemical Society of Japan

Volumn 83, Issue 8, 2010, Pages 923-934

  Iranpoor, Nasser ^a   Firouzabadi, Habib ^a   Khalili, Dariush ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDATION; AROMATIC AMINES; AZO COMPOUND; AZOPYRIDINE; BENZOTHIAZOLES; ISOXAZOLES; MITSUNOBU CONDITION; MITSUNOBU REACTIONS; N-BENZYLATION; PRIMARY AROMATIC AMINES; SIDE PRODUCTS; TRIPHENYL PHOSPHINES;

AMIDES; AROMATIC COMPOUNDS; AROMATIZATION; CARBOXYLIC ACIDS; FILTRATION; ORGANIC ACIDS;

AMINES;

EID: 77955839027     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20090269     Document Type: Article

References (90)

1. a) M. North, Contemp. Org. Synth. 1994, 1, 475.
2. b) C. E. Mabermann, in Encyclopedia of Chemical Technology, ed. by J. I. Kroschwitz, Wiley, New York, 1991, Vol.1, pp. 251266.
3. c) D. Lipp, in Encyclopedia of Chemical Technology, ed. by J. I. Kroschwitz, Wiley, New York, 1991, Vol.1, pp. 266287.
4. a) C. Lamberth, H.-J. Kempf, M. Križ, Pest Manage. Sci. 2007, 63, 57.
5. b) H. M. D. Navickiene, J. E. Miranda, S. A. Bortoli, M. J. Kato, V. S. Bolzani, M. Furlan, Pest Manage. Sci. 2007, 63, 399.
6. c) I. Yildiz Ören, E. Aki-Şener, C. ErtaŞ, Ö. Temiz-Arpaci, I. Yalçin, N. Altanlar, Turk. J. Chem. 2004, 28, 441.
7. d) I. Kobayashi, H. Muraoka, M. Hasegawa, T. Saika, M. Nishida, M. Kawamura, R. Ando, J. Antimicrob. Chemother. 2002, 50, 129.
8. e) E. Aki-Şener, K. K. Bingöl, Ö. Temiz-Arpaci, I. Yalçin, N. Altanlar, Il Farmaco 2002, 57, 451.
9. A. R. Katritzky, C. Cai, K. Suzuki, S. K. Singh, J. Org. Chem. 2004, 69, 811.
10. D.J.Dale, J. Draper, P. J. Dunn, M. L. Hughes, F. Hussain, P. C. Levett, G. B. Ward, A. S. Wood, Org. Process Res. Dev. 2002, 6, 767.
11. A. Shaabani, E. Soleimani, A. H. Rezayan, Tetrahedron Lett. 2007, 48, 6137.
12. a) M. B. Soellner, B. L. Nilsson, R. T. Raines, J. Org. Chem. 2002, 67, 4993.
13. b) E. Saxon, J. I. Armstrong, C. R. Bertozzi, Org. Lett. 2000, 2, 2141.
14. a) C. O. Kappe, Angew. Chem., Int. Ed. 2004, 43, 6250.
15. b) L. Perreux, A. Loupy, F. Volatron, Tetrahedron 2002, 58, 2155.
16. Y. Aoki, S. Kobayashi, J. Comb. Chem. 1999, 1, 371.
17. a) H. Fujiwara, Y. Ogasawara, K. Yamaguchi, N. Mizuno, Angew. Chem., Int. Ed. 2007, 46, 5202.
18. b) Ch. R. Reddy, P. P. Madhavi, A. S. Reddy, Tetrahedron Lett. 2007, 48, 7169.
19. c) E. Takács, C. Varga, R. Skoda-Földes, L. Kollár, Tetrahedron Lett. 2007, 48, 2453.
20. d) T. Maki, K. Ishihara, H. Yamamoto, Tetrahedron 2007, 63, 8645.
21. e) M. P. Cassidy, J. Raushel, V. V. Fokin, Angew. Chem., Int. Ed. 2006, 45, 3154.
22. f) E. Callens, A. J. Burton, A. G. M. Barrett, Tetrahedron Lett. 2006, 47, 8699.
23. g) K. Yamaguchi, M. Matsushita, N. Mizuno, Angew. Chem., Int. Ed. 2004, 43, 1576.
24. h) J. L. Davis, R. Dhawan, B. A. Arndtsen, Angew. Chem., Int. Ed. 2004, 43, 590.
25. i) J.-L. Liang, X.-Q. Yu, C.-M. Che, Chem. Commun. 2002, 124.
26. j) S. I. Lee, S. U. Son, Y. K. Chung, Chem. Commun. 2002, 1310.
27. F. Y. Rachinskii, T. G. Potapenko, O. D. Shapilov, V. T. Osipyan, A. A. Krupenina, Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.) 1968, 41, 1072.
28. a) M. B. Smith, J. March, March's Advanced Organic Chemistry, 6th ed., Wiley, New Jersy, 2007, p. 555.
29. b) K. Mohri, K. Suzuki, M. Usui, K. Isobe, Y. Tsuda, Chem. Pharm. Bull. 1995, 43, 159.
30. a) M. H. S. A. Hamid, J. M. J. Williams, Chem. Commun. 2007, 725.
31. b) Y. Watanabe, Y. Morisaki, T. Kondo, T. Mitsudo, J. Org. Chem. 1996, 61, 4214.
32. c) C.-H. Jun, D.-C. Hwang, S.-J. Na, Chem. Commun. 1998, 1405.
33. d) G. Bitsi, E. Schleiffer, F. Antoni, G. Jenner, J. Organomet. Chem. 1989, 373, 343.
34. a) R. Grigg, T. R. B. Mitchell, S. Sutthivaiyakit, N. Tongpenyai, J. Chem. Soc., Chem. Commun. 1981, 611.
35. b) T. Rische, B. Kitsos-Rzychon, P. Eilbracht, Tetrahedron 1998, 54, 2723.
36. K. Fujita, Z. Li, N. Ozeki, R. Yamaguchi, Tetrahedron Lett. 2003, 44, 2687.
37. M. S. R. Murty, B. Jyothirmai, P. R. Krishna, J. S. Yadav, Synth. Commun. 2003, 33, 2483.
38. M. Kimura, M. Futamata, K. Shibata, Y. Tamaru, Chem. Commun. 2003, 234.
39. F. Valot, F. Fache, R. Jacquot, M. Spagnol, M. Lemaire, Tetrahedron Lett. 1999, 40, 3689.
40. F. Matloubi Moghaddam, S. M. DokhtTaimoory, H. Ismaili, G. Rezanejade Bardajee, Synth. Commun. 2006, 36, 3599.
41. a) B.-C. Chen, J. E. Sundeen, P. Guo, M. S. Bednarz, R. Zhao, Tetrahedron Lett. 2001, 42, 1245.
42. b) A. K. Szardenings, T. S. Burkoth, G. C. Look, D. A. Campbell, J. Org. Chem. 1996, 61, 6720.
43. c) F. Fache, F. Valot, A. Milenkovic, M. Lemaire, Tetrahedron 1996, 52, 9777.
44. S. Salomaa, in The Chemistry of the Carbonyl Group, ed. by S. Patai, Wiley, New York, 1966, Vol.1, pp. 177210.
45. a) R. N. Salvatore, A. S. Nagle, K. W. Jung, J. Org. Chem. 2002, 67, 674.
46. b) C. Chiappe, D. Pieraccini, Green Chem. 2003, 5, 193.
47. a) O. Mitsunobu, Synthesis 1981, 1.
48. b) K. C. Kumara Swamy, N. N. Bhuvan Kumar, E. Balaraman, K. V. P. Pavan Kumar, Chem. Rev. 2009, 109, 2551.
49. a) E. A. Véliz, P. A. Beal, Tetrahedron Lett. 2006, 47, 3153.
50. b) D. P. Curran, R. Bajpai, E. Sanger, Adv. Synth. Catal. 2006, 348, 1621.
51. c) C. A. Fleckenstein, H. Plenio, Adv. Synth. Catal. 2006, 348, 1058.
52. d) A.-M. Bálint, A. Bodor, Á. Gömöry, K. Vékey, D. Szabó, J. Rábai, J. Fluorine Chem. 2005, 126, 1524.
53. e) A. M. Harned, H. S. He, P. H. Toy, D. L. Flynn, P. R. Hanson, J. Am. Chem. Soc. 2005, 127, 52.
54. a) T. Y. S. But, P. H. Toy, Chem. Asian J. 2007, 2, 1340.
55. b) S. Dandapani, D. P. Curran, Chem.-Eur. J. 2004, 10, 3130.
56. c) R. Dembinski, Eur. J. Org. Chem. 2004, 2763.
57. D. H. Valentine, Jr., J. H. Hillhouse, Synthesis 2003, 317, and the reference cited therein.
58. a) N. Iranpoor, H. Firouzabadi, N. Nowrouzi, Tetrahedron 2006, 62, 5498.
59. b) N. Iranpoor, H. Firouzabadi, N. Nowrouzi, Tetrahedron Lett. 2006, 47, 8247.
60. c) N. Iranpoor, H. Firouzabadi, B. Akhlaghinia, N. Nowrouzi, Tetrahedron Lett. 2004, 45, 3291.
61. d) N. Iranpoor, H. Firouzabadi, B. Akhlaghinia, R. Azadi, Synthesis 2004, 92.
62. e) N. Iranpoor, H. Firouzabadi, Gh. Aghapour, A. R. Vaez Zadeh, Tetrahedron 2002, 58, 8689.
63. N. Iranpoor, H. Firouzabadi, D. Khalili, S. Motevalli, J. Org. Chem. 2008, 73, 4882.
64. J. P. Launay, M. Tourrel-Pagis, J. F. Lipskier, V. Marvaud, C. Joachim, Inorg. Chem. 1991, 30, 1033.
65. a) F. Zaragoza, H. Stephensen, Tetrahedron Lett. 2000, 41, 1841.
66. b) S. S. Nikam, B. E. Kornberg, M. F. Rafferty, J. Org. Chem. 1997, 62, 3754.
67. c) T. Tsunoda, F. Ozaki, N. Shirakata, Y. Tamaoka, H. Yamamoto, S. Itô, Tetrahedron Lett. 1996, 37, 2463.
68. d) M. A. Walker, Tetrahedron Lett. 1996, 37, 8133.
69. e) R. C. Bernotas, R. V. Cube, Tetrahedron Lett. 1991, 32, 161.
70. f) J. R. Pfister, Synthesis 1984, 969.
71. M. L. Edwards, D. M. Stemerick, J. R. McCarthy, Tetrahedron 1994, 50, 5579.
72. a) Z. J. Jia, S. Kelberlau, L. Olsson, G. Anilkumar, B. Fraser-Reid, Synlett 1999, 565.
73. b) M. A. Walker, J. Org. Chem. 1995, 60, 5352.
74. D. L. Comins, G. Jianhua, Tetrahedron Lett. 1994, 35, 2819.
75. a) D. L. Hughes, R. A. Reamer, J. Org. Chem. 1996, 61, 2967.
76. b) J. A. Dodge, J. I. Trujillo, M. Presnell, J. Org. Chem. 1994, 59, 234.
77. a) CRC Handbook of Chemistry and Physics, 87th ed., ed. by D. R. Lide, CRC Press, London, 2006-2007.
78. b) Y. Saito, H. Ouchi, H. Takahata, Tetrahedron 2008, 64, 11129.
79. c) A. R. Katritzky, C. Cai, S. K. Singh, J. Org. Chem. 2006, 71, 3375.
80. d) W. J. Houlihan, V. A. Parrino, Y. Uike, J. Org. Chem. 1981, 46, 4511.
81. e) Z. Zhang, Y. Yu, L. S. Liebeskind, Org. Lett. 2008, 10, 3005.
82. f) A. K. Prasad, V. Kumar, S. Malhotra, V. T. Ravikumar, Y. S. Sanghvi, V. S. Parmar, Bioorg. Med. Chem. 2005, 13, 4467.
83. g) A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, K. Shudo, Tetrahedron Lett. 1989, 30, 6177.
84. h) I. Mohammadpoor-Baltork, H. R. Memarian, K. Bahrami, Monatsh. Chem. 2004, 135, 411.
85. i) M. J. Zacuto, F. Xu, J. Org. Chem. 2007, 72, 6298.
86. j) K. Fujita, Y. Enoki, R. Yamaguchi, Tetrahedron 2008, 64, 1943.
87. k) R. Apodaca, W. Xiao, Org. Lett. 2001, 3, 1745.
88. l) A. Heydari, S. Khaksar, M. Esfandyari, M. Tajbakhsh, Tetrahedron 2007, 63, 3363.
89. m) M. Zhang, J. D. Moore, D. L. Flynn, P. R. Hanson, Org. Lett. 2004, 6, 2657.
90. n) C. Guisado, J. E. Waterhouse, W. S. Price, M. R. Jorgensen, A. D. Miller, Org. Biomol. Chem. 2005, 3, 1049.