Functionalization of Baylis-Hillman bromides with symmetric and asymmetric bifunctional aromatics

Australian Journal of Chemistry

Volumn 60, Issue 3, 2007, Pages 205-210

  Zulykama, Yusuf ^a   Perumal, Paramasivan T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; SUBSTITUTION REACTIONS;

BIFUNCTIONAL AROMATICS; FUNCTIONALIZATION; NUCLEOPHILIC SUBSTITUTION PRODUCTS; SYNTHONS;

BROMINE COMPOUNDS;

EID: 34047121443     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH06342     Document Type: Article

References (30)

1. (a) S. E. Drewes, G. H. P. Roos, Tetrahedron 1988, 44, 4653. doi:10.1016/S0040-4020(01)86168-8
2. (b) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001. doi:10.1016/0040-4020(96)00154-8
3. (c) E. Ciganek, in Organic Reactions 1997, Vol. 51, Ch. 2, pp. 201-350 (Wiley: New York, NY).
4. (d) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811. doi:10.1021/CR010043D
5. (a) K. Y. Lee, J. M. Kim, J. N. Kim, Bull. Korean Chem. Soc. 2003, 24, 17.
6. (b) K. Y. Lee, J. M. Kim, J. N. Kim, Tetrahedron Lett. 2003, 44, 6737. doi:10.1016/S0040-4039(03)01648-4
7. (c) V. K. Aggarwal, A. Patin, S. Tisserand, Org. Lett. 2005, 7, 2555. doi:10.1021/OL050584F
8. (d) S. Chandrasekhar, D. Basu, Ch. Rambabu, Tetrahedron Lett. 2006, 47, 3059. doi:10.1016/J.TETLET.2006.03.037
9. (a) J. S. Yadav, B. V. Subba Reddy, A. K. Basak, A. V. Narasaiah, A. Prabhakar, B. Jagadeesh, Tetrahedron Lett. 2005, 46, 639. doi:10.1016/J.TETLET.2004.11.139
10. (b) V. Singh, R. Pathak, S. Kanojiya, S. Batra, Synlett 2005, 2465.
11. (c) C.-W. Cho, J.-R. Kong, M. J. Krische, Org. Lett. 2004, 6, 1337. doi:10.1021/OL049600J
12. (d) Y. Du, X. Han, X. Lu, Tetrahedron Lett. 2004, 45, 4967. doi:10.1016/J.TETLET.2004.04.135
13. (e) J. Li, X. Wang, Y. Zhang, Tetrahedron Lett. 2005, 46, 5233. doi:10.1016/J.TETLET.2005.05.107
14. (a) V. Singh, S. Batra, Synthesis 2006, 63. doi:10.1055/S-2005-918441
15. (b) S. Batra, A. K. Roy, Synthesis 2004, 2550. doi:10.1055/S-2004-831179
16. (c) D. Basavaiah, D. S. Sharada, A. Veerendhar, Tetrahedron Lett. 2004, 45, 3081. doi:10.1016/J.TETLET.2004.02.107
17. (d) S. Gowrisankar, K. Y. Lee, C. G. Lee, J. N. Kim, Tetrahedron Lett. 2004, 45, 6141. doi:10.1016/J.TETLET.2004.06.057
18. (a) D. Basavaiah, M. Bakthadoss, S. Pandiaraju, Chem. Commun. 1998, 1639. doi:10.1039/A804796K
19. (b) B. M. Trost, H.-C. Tsui, F. D. Toste, J.Am. Chem. Soc. 2000, 122, 3534. doi:10.1021/JA994326N
20. (c) D. Basavaiah, N. Kumaragurubaram, D. S. Sharada, R. M. Reddy, Tetrahedron 2001, 57, 8167. doi:10.1016/80040-4020(01) 00786-4
21. (d) O. Roy, A. Riahi, F. Henin, J. Muzart, Tetrahedron 2000, 56, 8133. doi:10.1016/S0040-4020(00)00727-4
22. (a) R. Buchholz, H. M. R. Hoffmann, Helv. Chim. Acta 1991, 74, 1213. doi:10.1002/HLCA.19910740608
23. (b) H.-Y. Chen, L. N. Patkar, S.-H. Ueng, C.-C. Lin, A. S.-Y. Lee, Synlett 2005, 2035. doi:10.1055/S-2005-871934
24. C. G. Lee, K. Y. Lee, S. Gowrisankar, J. N. Kim, Tetrahedron Lett. 2004, 45, 7409. doi:10.1016/J.TETLET.2004.08.075
25. S. C. Kim, S. Gowrisankar, J. N. Kim, Bull. Korean Chem. Soc. 2005, 26, 1001.
26. C. G. Lee, K. Y. Lee, S. Lee, J. N. Kim, Tetrahedron 2005, 61, 1493. doi:10.1016/J.TET.2004.11.082
27. J. M. Kim, K. Y. Lee, J. N. Kim, Bull. Korean Chem. Soc. 2002, 23, 1055.
28. Addition products of o-phenylenediamine and 2-aminophenol were found to decompose with time.
29. For Baylis-Hillman adduots see: (a) V. K. Aggarwal, A. Mereu, Chem. Commun. 1999, 2311. doi:10.1039/A907754E
30. (b) C. Yu, B. Liu, L. Hu, J. Org. Chem. 2001, 66, 5413. doi:10.1021/JO015628M