Simple and selective one-pot replacement of the N-methyl group of tertiary amines by quaternization and demethylation with sodium sulfide or potassium thioacetate: An application to the synthesis of pergolide

Journal of the Chemical Society. Perkin Transactions 1

Volumn 1, Issue 19, 2001, Pages 2398-2403

  Anastasia, Luigi ^a   Cighetti, Giuliana ^a   Allevi, Pietro ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMMONIUM COMPOUNDS; POTASSIUM COMPOUNDS; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

DEMETHYLATION;

AMINES;

EID: 0034740847     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b104843k     Document Type: Article

References (17)

1. J.H. Cooley, E.J. Evain Synthesis 1989, 1.
2. J. von Braun Ber. Dtsch. Chem. Ges. 1900, 33, 1438.
3. J.D. Hobson, J.G. McCluskey J. Chem Soc. C 1967, 2015.
4. A. Coop, J.W. Janetka, J.W. Lewis, K.C. Rice J. Org. Chem. 1998, 63, 4392.
5. G.H. Posner, J.-S. Ting Synth. Commun. 1974, 4, 355.
6. M. Shamma, N.C. Deno, J.F. Remar Tetrahedron Lett. 1966, 1375.
7. T.S. Manoharan, K.M. Madyastha, B.B. Singh, S.P. Bhatnagar, U. Weiss Synthesis 1983, 809.
8. R.O. Hutchins, F.J. Dux J. Org. Chem. 1973, 38, 1961.
9. J.W. Misner, J.H. Kennedy, W.S. Biggs Org. Process. Res. Dev. 1997, 1, 77.
10. J.W. Misner, U.S. Pat., 5 463 060, 1995 (Chem. Abstr., 1994, 120, 270946v).
11. E.C. Kornfeld and N.J. Bach, US Pat., 4 166 182, 1979, (Chem. Abstr., 1980, 92, 181450q).
12. D.J. Sprankle and E.C. Jensen, in Analytical Profiles of Drug Substances and Excipients, ed. H. G. Brittain, Academic Press, New York, 1992, vol. 21, p. 375.
13. T. Kametani, K. Kigasawa, M. Hiiragi, N. Wagatsuma, K. Wakisaka Tetrahedron Lett. 1969, 635.
14. W.C. Still, M. Kahn, A. Mitra J. Org. Chem. 1978, 43, 2923.
15. J. Krepelka, A. Cerny, R. Kotva, M. Semonsky Collect. Czech. Chem. Commun. 1977, 42, 1209.
16. J.M.Z. Gladych, E.P. Taylor J. Chem. Soc. 1962, 1481.
17. A.L. Mndzhoyan, V.A. Mnatsakanyan, L.S. Arutyunyan Arm. Khim. Zh. 1969, 22, 842 Chem. Abstr. 1970, 72, 21808w.