DMAP catalyzed reaction of β-ketoesters and dimethyl acetylenedicarboxylate: efficient synthesis of polysubstituted benzenes and biaryls

Tetrahedron

Volumn 62, Issue 43, 2006, Pages 10136-10140

  Nair, Vijay ^a   Vidya, N ^a   Biju, A T ^a   Deepthi, Ani ^a   Abhilash, K G ^a   Suresh, Eringathodi ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Ketoesters; Biaryl; DMAD; DMAP

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; BENZENE DERIVATIVE; BETA OXOCARBOXYLIC ACID ESTER; DIMETHYLAMINOPYRIDINE; ESTER; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DESICCATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 33748440197     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.031     Document Type: Article

References (37)

1. Saito S., and Yamamoto Y. Chem. Rev. 100 (2000) 2901
2. Sakakibara T., Tanaka Y., and Yamasaki S. Chem. Lett. 5 (1986) 797
3. Sato S., Isobe T., Ushijima T., and Nakamura E. Tetrahedron 61 (2005) 11449
4. Mohanakrishnan A.K., and Prakash C. Synlett (2005) 2224
5. Eyley S.C. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, New York, NY 707
6. Heaney H. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, New York, NY 733
7. Olah G.A. Friedel-Crafts Chemistry (1973), Wiley, New York, NY
8. Gilman H., and Bebb R.L. J. Am. Chem. Soc. 61 (1939) 109
9. Wittig G., and Fuhrman G. Chem. Ber. 73 (1940) 1197
10. Snieckus V. Chem. Rev. 90 (1990) 879
11. Reppe W., and Schweckendiek W.J. Justus Liebigs Ann. Chem. 560 (1948) 104
12. Suzuki D., Urabe H., and Sato F. J. Am. Chem. Soc. 123 (2001) 7925
13. Vollhardt K.P.C. Acc. Chem. Res. 10 (1977) 1
14. Vollhardt K.P.C. Angew. Chem., Int. Ed. Engl. 23 (1984) 539
15. Xi C., Chen C., Lin J., and Hong X. Org. Lett. 7 (2005) 347
16. Takahashi T., Xi Z., Yamazaki A., Liu Y., Nakajima K., and Kotora M. J. Am. Chem. Soc. 120 (1998) 1672
17. Yamamoto Y., Ishii J., Nishiyama H., and Itoh K. J. Am. Chem. Soc. 126 (2004) 3712
18. Arakawa T., Ogawa R., and Itoh K. J. Am. Chem. Soc. 125 (2003) 12143
19. Jhones R.R., and Bergman R.G. J. Am. Chem. Soc. 94 (1972) 660
20. Bergman R.G. Acc. Chem. Res. 6 (1973) 25
21. Hassan J., Sèvignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359
22. Bringmann G., Mortimer A.J.P., Keller P.A., Gesser M.J., Garner J., and Breuning M. Angew. Chem., Int. Ed. 44 (2005) 5384
23. Kraft A., Grimsdale A.C., and Holmes A.B. Angew. Chem., Int. Ed. 37 (1998) 402
24. Roncali J. Chem. Rev. 92 (1992) 711
25. Ullmann F., and Bielecki. J. Chem. Ber. 34 (1901) 2174
26. Gant T.G., and Meyers A.I. Tetrahedron 50 (1994) 2297
27. Studer A., Bossart M., and Vasella T. Org. Lett. 2 (2000) 985
28. Clive D.L.J., and Kang S. Tetrahedron Lett. 41 (2000) 1315
29. Bringmann G., and Tasler S. Tetrahedron 57 (2001) 331
30. Huisgen R., and Rist H. Justus Liebigs Ann. Chem. 594 (1955) 137
31. Nair V., Rajesh C., Vinod A.U., Bindu S., Sreekanth A.R., Mathen J.S., and Balagopal L. Acc. Chem. Res. 36 (2003) 899
32. Nair V., Sreekanth A.R., Abhilash N., Biju A.T., Remadevi B., Menon R.S., Rath N.P., and Srinivas R. Synthesis (2003) 1895
33. Nair V., Pillai A.N., Menon R.S., and Suresh E. Org. Lett. 7 (2005) 1189
34. Nair V., Pillai A.N., Beneesh P.B., and Suresh E. Org. Lett. 7 (2005) 4625
35. The crystal structure for compound 8d had been deposited at the Cambridge Crystallographic Data Center and allocated the reference no. CCDC 295899.
36. Taber D.F., Deker P.B., and Gaul M.D. J. Am. Chem. Soc. 109 (1987) 7488
37. Holmquist C.R., and Roskamp E.J. J. Org. Chem. 54 (1989) 3258