Pyridine/potassium tert-butoxide catalyzed benzannulation of β-diketones with dimethyl acetylenedicarboxylate

Synthesis

Volumn , Issue 24, 2009, Pages 4137-4142

  Hu, Bin ^a   Meng, Ling Guo ^a   Liu, Yan Ling ^a   Liang, Mao ^a   Xue, Song ^a  

^a TIANJIN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

diketones; Benzannulation; Dimethyl acetylenedicarboxylate; Potassium tert butoxide; Pyridine

Indexed keywords

BENZANNULATION; BENZANNULATION REACTION; DIKETONES; DIMETHYL ACETYLENEDICARBOXYLATE; HIGH YIELD; POTASSIUM TERT-BUTOXIDE; STARTING MATERIALS; SUBSTITUTED BENZENES;

BENZENE; CATALYSIS; POTASSIUM; PYRIDINE; REACTION KINETICS;

KETONES;

1,3 DIKETONE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; POTASSIUM DERIVATIVE; POTASSIUM TERT BUTOXIDE; PYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; BENZANNULATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CYCLOADDITION; POLYMERIZATION; PROTON TRANSPORT; REACTION TIME;

EID: 78650719396     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217035     Document Type: Article

References (35)

1. (a) Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002.
2. (b) Eyley, S. C. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 707.
3. (a) Kotha, T.; Brahmachary, E.; Lahiri, K. Eur. J. Org. Chem. 2005, 4741.
4. (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
5. (c) Vollhardt, K. P. C. Ang. Chem. Int. Ed. Engl. 1984, 23, 539.
6. (a) Xi, Z.; Sato, K.; Gao, Y.; Lu, J.; Takahashi, T. J. Am. Chem. Soc. 2003, 125, 9568.
7. (b) Takahashi, T.; Ishikawa, M.; Huo, S. J. Am. Chem. Soc. 2002, 124, 388.
8. (c) Langer, P.; Bose, G. Angew. Chem. Int. Ed. 2003, 42, 4033.
9. (d) Katritzky, A. R.; Li, J.; Xie, L. Tetrahedron 1999, 55, 8263.
10. Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187.
11. Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925.
12. (a) Tius, M. A.; Gomez-Galeno, J. Tetrahedron Lett. 1986, 27, 2571.
13. (b) Chan, T. H.; Prasad, C. V. C. J. Org. Chem. 1986, 51, 3012.
14. (a) Serra, S.; Fuganti, C.; Moro, A. J. Org. Chem. 2001, 66, 7883.
15. (b) Turnbull, P.; Moore, H. W. J. Org. Chem. 1995, 60, 644.
16. (a) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
17. (b) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
18. (c) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901.
19. (d) Cowen, B. J.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 1098
20. (e) Ye, L.-W.; Sun, X.-L.; Wang, Q.-G.; Tang, Y. Angew. Chem. Int. Ed. 2007, 46, 5951.
21. (f) Ye, L.-W.; Han, X.; Sun, X.-L.; Tang, Y. Tetrahedron 2008, 64, 1487.
22. (g) Denmark, S. E.; Beutner, G. L. Angew. Chem. Int. Ed. 2008, 47, 1560.
23. (h) Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140.
24. (a) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677.
25. (b) Shi, Y.-L.; Shi, M. Chem. Eur. J. 2006, 12, 3374.
26. (c) Gabillet, S.; Lecerclé, D.; Loreau, O.; Carboni, M.; Dézard, S.; Gomis, J.-M.; Taran, F. Org. Lett. 2007, 9, 3925.
27. (d) Zhu, X.-F.; Henry, C. E.; Wang, J.; Dudding, T.; Kwon, O. Org. Lett. 2005, 7, 1387.
28. (e) Zhu, X.-F.; Schaffner, A.-P.; Li, R. C.; Kwon, O. Org. Lett. 2005, 7, 2977.
29. (f) Wurz, R. P.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 12234.
30. (g) Nair, V.; Menon, R. S.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520.
31. (h) Fang, Y.-Q.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 5660.
32. Zhou, Q.-F.; Yang, F.; Guo, Q.-X.; Xue, S. Synlett 2007, 2073.
33. Zhou, Q.-F.; Yang, F.; Guo, Q.-X.; Xue, S. Synlett 2007, 215.
34. Nair, V.; Vidya, N.; Biju, A. T.; Deepthi, A.; Abhilash, K. G.; Suresh, E. Tetrahedron 2006, 62, 10136
35. 3; F000 = 928; Residuals: R, Rw: 0.0597, 0.1465.