A new and facile route for the synthesis of thiocarbamates from aniline, carbon monoxide, and thiols mediated by selenium

Chemistry Letters

Volumn 34, Issue 4, 2005, Pages 606-607

  Zhang, Xiaopeng ^a,b   Lu, Shiwei ^a,b  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; CARBON MONOXIDE; SELENIUM; THIOCARBAMIC ACID DERIVATIVE; THIOL DERIVATIVE; TRIETHYLAMINE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; REACTION ANALYSIS; RECYCLING;

EID: 21544435661     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.606     Document Type: Article

References (34)

1. a) M. Beji, H. Sbihi, A. Baklouti, and A. Cambon, J. Fluorine Chem., 99, 17 (1999).
2. b) A. Goel, S. J. Mazur, R. J. Fattah, T. L. Hartman, J. A. Turpin, M. Huang, W. G. Rice, E. Appella, and J. K. Inman, Bioorg. Med. Chem. Lett., 12, 767 (2002).
3. c) Y. Oku, K. Sakuma, K. Yokoyama, and M. Miyaji, Nippon Ishinkin Gakkai Zasshi, 43, 181 (2002).
4. a) M. Xue, B. H. Long, C. Fairchild, K. Johnston, W. C. Rose, J. F. Kadow, D. M. Vyas, and S. H. Chen, Bioorg. Med. Chem. Lett., 10, 1327 (2000).
5. b) H. G. Hahn, H. K. Rhee, C. K. Lee, and K. J. Whang, Korean J. Med. Chem., 10, 66 (2000).
6. a) J. L. Harwood, Biochem. Soc. Trans., 22, 621 (1994).
7. b) S. Yoshida, T. Abe, M. Furushima, T. Maruyama, Jpn. Kokai Tokkyo Koho JP 06256117.
8. a) Z. S. Li-Pan, H. V. Joshi, and G. A. Digenis, J. Enzyme Inhib., 15, 63 (1999).
9. b) N. P. Rodis, and G. A. Digenis, J. Enzyme Inhib., 16, 95 (2001).
10. c) R. M. Nathan and C. J. Peter, J. Med. Chem., 46, 1066 (2003).
11. a) "The Pesticide Mannal," 9th ed., ed. by C. R. Worthing, British Crop Protection Council, London (1991).
12. b) W. A. Breiter, J. M. Baker, and W. C. Koskinen, J. Agric. Food Chem., 46, 1624 (1998).
13. c) S. J. Lee, P. Caboni, M. Tomizawa, and J. E. Casida, J. Agric. Food Chem., 52, 95 (2004).
14. a) Y. S. Chen, I. Schuphan, and J. E. Casida, J. Agric. Food Chem., 27, 709 (1979).
15. b) H. J. Sanders, Chem. Eng. News, 59, 20 (1981).
16. c) T. Mizuno, I. Nishiguchi, T. Okushi, and T. Hirashima, Tetrahedron Lett., 32, 6867 (1991).
17. d) Y. Nagao, Y. Abe, T. Misono, N. Ichizen, Y. Shima, H. Iesaka, and M. Furushima, Nippon Kagaku Kaishi, 1993, 719.
18. e) N. Sonoda, T. Mizuno, S. Murakami, K. Konda, A. Ogawa, and I. Ryu, Angew. Chem., Int. Ed. Engl., 28, 452 (1989).
19. a) T. Mizuno, I. Nishiguchi, and N. Sonoda, Tetrahedron, 50, 5669 (1994).
20. b) T. Mizuno, T. Daigaku, and I. Nishiguchi, Tetrahedron Lett., 36, 1533 (1995).
21. c) T. Mizuno, T. Junko, and A. Ogawa, Tetrahedron, 59, 1327 (2003).
22. d) T. Mizuno, T. Iwai, A. Ogawa, and T. Ito, Tetrahedron, 60, 2869 (2004).
23. a) H. Kwart and E. R. Evans, J. Org. Chem., 31, 410 (1966).
24. b) R. E. Hackler and T. W. Balko, J. Org. Chem., 38, 2106 (1973).
25. c) M. Sakamoto, M. Yoshiaki, M. Takahashi, T. Fujita, and S. Watanabe, J. Chem. Soc., Perkin Trans. I, 1995, 373.
26. d) A. Bohme and H. J. Gais, Tetrahedron: Asymmetry, 10, 2511 (1999).
27. A. Ricci, R. Danieli, and G. Pirazzini, J. Chem. Soc., Perkin Trans. I, 1977, 1069.
28. a) W. D. Jones, K. A. Reynolds, C. K. Sperry, R. J. Lachicotte, S. A. Godleski, and R. R. Valente, Organometallics, 19, 1661 (2000).
29. b) J. Jacob, K. A. Reynolds, W. D. Jones, S. A. Godleski, and R. R. Valente, Organometallics, 20, 1028 (2001).
30. P. Koch, Tetrahedron Lett., 25, 2087 (1975).
31. N. Sonoda, G. Yamamoto, K. Natsukawa, K. Kondo, and S. Murai, Tetrahedron Lett., 24, 1969 (1975).
32. J. H. Wynne, S. D. Jensen, and A. W. Snow, J. Org. Chem., 68, 3733 (2003).
33. 3) δ 7.42-7.07 (m,6H), 2.95 (t, J = 8.0 Hz, 2H), 1.68 (sextet, J = 8.0 Hz, 2H), 0.99 (t, J = 8.0 Hz, 3H).
34. R. S. Birch, W. S. Gowan, and P. Norris, J. Chem. Soc., 127, 904 (1925).