Acylation, cyanoethylation and alkylation of methyl and phenyl indolylmagnesium salts: Influence of the substituents on the C- and N- reaction products

Journal of Heterocyclic Chemistry

Volumn 36, Issue 1, 1999, Pages 129-135

  Rodríguez, J Gonzalo ^a   Urrutia, Anahí ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLONITRILE; MAGNESIUM SALT;

ACYLATION; ALKYLATION; ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; CYCLIZATION;

EID: 0032906007     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570360119     Document Type: Article

References (29)

1. R. M. Acheson, An Introduction to the Chemistry of Heterocyclic Compounds, 3rd Ed, Wiley-Interscience, New York, 1976; T. L. Gilchrist, Química Heterocíclica, 2nd. Ed, Addison-Wesley Iberoamericana, Wilmington, Delaware, 1995.
2. R. M. Acheson, An Introduction to the Chemistry of Heterocyclic Compounds, 3rd Ed, Wiley-Interscience, New York, 1976; T. L. Gilchrist, Química Heterocíclica, 2nd. Ed, Addison-Wesley Iberoamericana, Wilmington, Delaware, 1995.
3. [a] C. Pyun, J. Org. Chem., 37, 3066 (1972);
4. [b] W. C. Guida and D. J. Mathre, J. Org. Chem., 45, 3172 (1980);
5. [c] E. V. Dehmlow, Angew. Chem., Int. Ed. Engl., 16, 493 (1977);
6. [d] K. Sukata, Bull. Chem. Soc. Japan., 56, 280 (1983).
7. R. G. Pearson, Hard and Soft Acids and Bases, Dowden Hutchinson and Ross, Inc., Stroudsburg, PA, 1973.
8. G. M. Rubottom and J. C. Chabala, Synthesis, 566 (1972); H. Heaney and S.V. Ley, J. Chem. Soc., Perkin Traits. I, 499 (1973).
9. G. M. Rubottom and J. C. Chabala, Synthesis, 566 (1972); H. Heaney and S.V. Ley, J. Chem. Soc., Perkin Traits. I, 499 (1973).
10. V. Bocchi, G. Casnati, A. Dossena and F. Villani, Synthesis , 414 (1976), N. Wang, K. Teo and H. J. Anderson, Can. J. Chem., 55, 4112 (1977).
11. V. Bocchi, G. Casnati, A. Dossena and F. Villani, Synthesis , 414 (1976), N. Wang, K. Teo and H. J. Anderson, Can. J. Chem., 55, 4112 (1977).
12. E. Santaniello, C. Farachi and F. Ponti, Synthesis, 617 (1979).
13. C. Mateo, A. Urrutia, J. G. Rodríguez, I. Fonseca, and F. H. Cano, J. Org. Chem., 61, 810 (1996).
14. [a] R. Marchelli, O. Hutzinger, R. A. Heacock, Can. J. Chem., 23, 4375 (1969);
15. [b] J. I. DeGraw and J. G. Kennedy, J. Heterocyclic Chem., 3, 90 (1966);
16. [c] T. E. Young and M. F. Mizianty, J. Org. Chem., 29, 2030 (1964).
17. B. Carnati and A. Pochini, Chim. Ind. (Milan), 49, 172 (1967).
18. J. G. Rodríguez and A. San Andrés, J. Heterocyclic Chem., 28, 1293 (1991).
19. Reactions were made in a previously flamed-dried Schlenk tube, under a positive argon pressure. The system was successively placed at reduced pressure (0.9 torr), charged with argon and the operation was repeated three times. All the reagent solutions were purged with argon and charged through a septum under positive argon pressure.
20. J. Catalán, V. López, P. Pérez, R. Martín-Villamil and J. G. Rodríguez, Liebigs Ann. Chem., 241 (1995).
21. M. P. Martinez-Alcazar, I. Fonseca, F. H. Cano, J. G. Rodríguez and A. Urrutia, Acta Cryst., C53, 1345 (1997).
22. M. E. Specter and W. C. Anthony, J. Am. Chem. Soc., 76, 6208 (1954); H. Wieland, W. Konz and H. Mittasch, Liebigs Ann. Chem., 1, 513 (1934); S. Akabori and S. Kaito, Ber., 63, 2245 (1930).
23. M. E. Specter and W. C. Anthony, J. Am. Chem. Soc., 76, 6208 (1954); H. Wieland, W. Konz and H. Mittasch, Liebigs Ann. Chem., 1, 513 (1934); S. Akabori and S. Kaito, Ber., 63, 2245 (1930).
24. M. E. Specter and W. C. Anthony, J. Am. Chem. Soc., 76, 6208 (1954); H. Wieland, W. Konz and H. Mittasch, Liebigs Ann. Chem., 1, 513 (1934); S. Akabori and S. Kaito, Ber., 63, 2245 (1930).
25. J. C. Powers, J. Org. Chem., 30, 2534 (1965).
26. H. Buder, W. Oroshnik, J. Am. Chem. Soc., 81, 163 (1959).
27. J .G. Rodríguez, To be published.
28. D. Desmaële and J d'Angelo, J. Org. Chem., 59, 2292 (1994).
29. J. E. Baldwin, J. Chem Soc., Chem. Commun., 734 (1976).