One-pot synthesis of amine-substituted aryl sulfides and benzo[ b ]thiophene derivatives

Organic Letters

Volumn 12, Issue 10, 2010, Pages 2430-2433

  Duan, Zhongyu ^a   Ranjit, Sadananda ^a   Liu, Xiaogang ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BENZOTHIOPHENE; SULFIDE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFIDES; THIOPHENES;

EID: 77952403309     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100816g     Document Type: Article

References (45)

1. Marcincal-Letebvre, A.; Gesquiere, C.; Lemer, C.; Dupuis, B. J. Med. Chem. 1981, 24, 889
2. Liu, G.; Link, J. T.; Pei, Z.; Reilly, E. B.; Leitza, S.; Nguyen, B.; Marsh, K. C.; Okasinski, G. F.; von Geldem, T. W.; Ormes, M.; Fowler, K.; Gallatin, M. J. Med. Chem. 2000, 43, 4025
3. Gangjee, A.; Zeng, Y.; Talreja, T.; McGuire, J. J.; Kisliuk, R. L.; Queener, S. F. J. Med. Chem. 2007, 50, 3046
4. Jarkas, N.; McConathy, J.; Voll, R. J.; Goodman, M. M. J. Med. Chem. 2005, 48, 4254
5. Carril, M.; SanMartin, R; Dominguez, E.; Tellitu, I. Chem.- Eur. J. 2007, 13, 5100
6. Zhang, H.; Cao, W.; Ma, D. Synth. Commun. 2007, 37, 25
7. Wong, Y. C.; Jayanth, T. T.; Cheng, C.H. Org. Lett. 2006, 8, 5613
8. Fernandez-Rodriguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180
9. Ham, J.; Cho, S. J.; Ko, J.; Chin, J.; Kang, H. J. Org. Chem. 2006, 71, 5781
10. Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem. 2009, 74, 3189
11. Fernandez-Rodriguez, M. A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1163
12. Feng, Y.; Wang, H.; Sun, F.; Li, Y.; Fu, X.; Jin, K. Tetrahedron 2009, 65, 9737
13. Taniguchi, N. J. Org. Chem. 2004, 69, 6904
14. Sperotto, E.; Klink, G. P. M. V.; Vries, J. G. D.; Koten, G. V. J. Org. Chem. 2008, 73, 5625
15. Jarkas, N.; McConathy, J.; Voll, R. J.; Goodman, M. M. J. Med. Chem. 2005, 48, 4254
16. Wrobel, Z. Tetrahedron 2003, 59, 101
17. Taniguchi, N. J. Org. Chem. 2007, 72, 1241
18. Taniguchi, N. Synlett 2006, 9, 1351
19. Varala, R.; Ramu, E.; Alam, M. M.; Adapa, S. R. Chem. Lett. 2004, 33, 1614
20. Heldebrant, D.; Jessop, P. G. J. Am. Chem. Soc. 2003, 125, 5600
21. Perrier, S.; Gemici, H.; Li, S. Chem. Commun. 2004, 604
22. Zhang, Z.-H.; Yin, L.; Wang, Y.-M.; Liu, J.-Y.; Li, Y. Green Chem. 2004, 6, 563
23. Chandrasekhar, S.; Narsihmulu, Ch.; Shameem Sultana, S.; Ramakrishna Redd, N. Org. Lett. 2002, 4, 4399
24. Wang, L.; Zhang, Y.; Liu, L.; Wang, Y. J. Org. Chem. 2006, 71, 1284
25. Tzitzios, V.; Basina, G.; Gjoka, M.; Alexandrakis, V.; Georgakilas, V.; Niarchos, D.; Boukos, N.; Petridis, D. Nanotechnology 2006, 17, 3750
26. Agrawal, A.; Tratnyek, P. G. Environ. Sci. Technol. 1995, 30, 153
27. Fry, A. J. In The Chemistry of Amino, Nitroso, and Nitro Compounds and Their Derivatives; Patai, S., Ed.; Wiley-Interscience: Chichester, 1982.
28. Zuman, P.; Shah, B. Chem. Rev. 1994, 94, 1621
29. Smentowski, F. J. J. Am. Chem. Soc. 1963, 85, 3036
30. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367
31. Hutchinson, I.; Jennings, S. A.; Vishnuvajjala, B. R.; Westwell, A. D.; Stevens, M. F. G. J. Med. Chem. 2002, 45, 744
32. Gao, H.; Katzenellenbogen, J. A.; Garg, R.; Hansch, C. Chem. Rev. 1999, 99, 723
33. McInerney, E.; Katzenellenbogen, B. S. J. Biol. Chem. 1996, 271, 24172
34. Kondolff, I.; Santelli, H. D. M. J. Heterocycl. Chem. 2008, 45, 109
35. Yasuike, S.; Qin, W.; Sugawaraa, Y.; Kuritaa, J. Tetrahedron Lett. 2007, 48, 721
36. Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997
37. Yang, S.; Sun, C.; Fang, Z.; Li, B.; Li, Y.; Shi, Z Angew. Chem., Int. Ed. 2008, 47, 1473
38. Nandurkar, N. S.; Bhanushali, M. J.; Bhor, M. D.; Bhanage, B. M. Tetrahedron Lett. 2008, 49, 1045
39. Chiong, H. A.; Daugulis, O. Org. Lett. 2007, 9, 1449
40. Bíró, A. B.; Kotschy, A. Eur. J. Org. Chem. 2007, 8, 1364
41. Aitken, R. A.; Burns, G. J. Chem. Soc., Perkin Trans. 1 1994, 17, 2455
42. Arnoldi, A.; Carughi, M. Synthesis 1988, 2, 155
43. Nishhio, T.; Okuda, N.; Kashima, C. J. Heterocycl. Chem. 1988, 25, 1437
44. Duan, Z.; Ranjit, S.; Zhang, P.; Liu, X. Chem.- Eur. J. 2009, 15, 3666
45. Beutler, U.; Fuenfschilling, P. C.; Steinkemper, A. Org. Process Res. Dev. 2007, 11, 341