The solid-state Michael addition of indole to 4-arylidene-3-methyl-5- pyrazolone

Journal of Heterocyclic Chemistry

Volumn 36, Issue 3, 1999, Pages 697-701

  Li, Xiao Liu ^a,b   Wang, Yong Mei ^a   Matsuura, Teruo ^a   Meng, Ji Ben ^a  

^a NANKAI UNIVERSITY   (China)

^b AGRICULTURAL UNIVERSITY OF HEBEI   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE; PYRAZOLONE DERIVATIVE;

ARTICLE; REACTION ANALYSIS; SOLID STATE; SYNTHESIS;

EID: 0032779606     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570360320     Document Type: Article

References (24)

1. G. R. Desiraju, Organic Solid State Chemistry, Elsevier, Amsterdam, 1987.
2. For reviews on organic solid state reactions, see: [a] F. Toda, Synlett, 5, 303 (1993); [b] N. B. Singh, R. J. Singh and N. P. Singh, Tetrahedron, 50, 6441 (1994); [c] G. R. Desiraju, Organic Solid State Chemistry, Elsevier Science Publishers, Amsterdam, 1987; [d] X. L. Li, Y. M. Wang, J. B. Meng and C. P. Du, Youji Huaxue, 18, 20 (1998).
3. For reviews on organic solid state reactions, see: [a] F. Toda, Synlett, 5, 303 (1993); [b] N. B. Singh, R. J. Singh and N. P. Singh, Tetrahedron, 50, 6441 (1994); [c] G. R. Desiraju, Organic Solid State Chemistry, Elsevier Science Publishers, Amsterdam, 1987; [d] X. L. Li, Y. M. Wang, J. B. Meng and C. P. Du, Youji Huaxue, 18, 20 (1998).
4. For reviews on organic solid state reactions, see: [a] F. Toda, Synlett, 5, 303 (1993); [b] N. B. Singh, R. J. Singh and N. P. Singh, Tetrahedron, 50, 6441 (1994); [c] G. R. Desiraju, Organic Solid State Chemistry, Elsevier Science Publishers, Amsterdam, 1987; [d] X. L. Li, Y. M. Wang, J. B. Meng and C. P. Du, Youji Huaxue, 18, 20 (1998).
5. For reviews on organic solid state reactions, see: [a] F. Toda, Synlett, 5, 303 (1993); [b] N. B. Singh, R. J. Singh and N. P. Singh, Tetrahedron, 50, 6441 (1994); [c] G. R. Desiraju, Organic Solid State Chemistry, Elsevier Science Publishers, Amsterdam, 1987; [d] X. L. Li, Y. M. Wang, J. B. Meng and C. P. Du, Youji Huaxue, 18, 20 (1998).
6. F. Toda and H. Akai, J. Org. Chem., 55, 3446 (1990).
7. F. Toda, K. Tanaka and J. Sato, Tetrahedron Asymmetry, 4, 1771 (1993).
8. M. Smricina, S. Vyskocil, V. Hanus, M. Polasek, V. Langer, B. G. M. Chew, D. B. Zax, H. Verrier, K. Harper, T. A. Claxton and P. Kocovsky, J. Am. Chem. Soc., 118, 487 (1996).
9. J. B. Meng, H. Ma and Y. M. Wang, Chin. Chem. Letters, 4, 475 (1993).
10. [a] D. M. Du, S. M. Meng, Y. M. Wang, J. B. Meng and X. Z. Zhou, Chin. J. Chem., 13, 520 (1995);
11. [b] D. M. Du, S. M. Meng, Y. M. Wang, J. B. Meng, X. Z. Zhou and Y. Zhu, Chin. J. Struct. Chem., 14, 277 (1995).
12. J. B. Meng, D. M. Du, Y. M. Wang, R. J. Wang and H. G. Wang, Chin. Chem. Letters, 3, 247 (1992).
13. J. B. Meng, Z. Wen, Y. M. Wang and H. G. Wang, Chin. Chem. Letters, 4, 865 (1993).
14. X. L. Li, H. Ma, Y. M. Wang and J. B. Meng, Chem. J. Chinese Univ., 16, 1903 (1996).
15. Y. M. Wang, Z. Wen, X. M. Chen, D. M. Du, T. Matsuura and J. B. Meng, J. Heterocylic Chem., 35, 313 (1998).
16. X. L. Li, Y. M. Wang, B. Tian, T. Matsuura and J. B. Meng, J. Heterocylic Chem., 35, 129 (1998).
17. W. A. Remers, Properties and Reactions of Indoles, Isoindoles and their Hydrogenated Derivatives in Indole, Part One, W. J. Houlihan, ed, John Wiley and Sons Inc., New York, 1972, pp 1-226.
18. J. Szmuzkovicz, J. Am. Chem. Soc., 79, 2819, (1957).
19. W. E. Noland and R. F. Lange, J. Am. Chem. Soc., 81, 1203, (1959).
20. Z. Iqeal, A. H. Jaackson and K. R. N. Rao, Tetrahedron Letters, 29, 2577, (1988).
21. R. Dworczak, W. M. F. Fabian, H. Sterk, C. Kratky and H. Junek, Liebigs Ann. Chem., 7, (1992).
22. max (dimethyl sulfoxide): 409.5 nm (log ε = 3.86).
23. M. Abdel-Rahman and H. Abdel-Ghany, Synth. Commun, 19, 1987 (1989).
24. E. D. Berganann, D. Ginsberg and R. Pappo, The Michael Reaction, in Organic Reactions, Vol. 10, R. Adams, ed, John Wiley and Sons Inc., New York, 1959, p 179.