Pyridinium chloride: A new reagent for N-demethylation of N-methylazinium derivatives

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6205-6208

  Ruiz, Anthony ^a   Rocca, Patrick ^a   Marsais, Francis ^a   Godard, Alain ^a   Quéguiner, Guy ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; METHYLAZINIUM DERIVATIVE; PYRIDINIUM DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; DEMETHYLATION; DRUG SYNTHESIS; REACTION ANALYSIS; REACTION TIME;

EID: 0030877117     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01399-3     Document Type: Article

References (22)

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2. Royer, R.; Demerseman, P. Bull. Soc. Chim. Fr. 1968, 2633-2648. Radl, S. Chem. Listy 1985, 79, 1233-1255.
3. Royer, R.; Bachelet, J.-P.; Demerseman, P. Bull. Soc. Chim. Fr. 1973, 611-615.
4. Trécourt, F.; Quéguiner, G. J. Chem. Res. M 1982, 912-942, S 1982, 76-77.
5. Trécourt, F.; Quéguiner, G. J. Chem. Res. M 1982, 912-942, S 1982, 76-77.
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7. Mongin, F.; Mongin, O.; Trécourt, F.; Godard, A.; Quéguiner, G. Tetrahedron Lett. 1996, 37, 6695-6698.
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9. a: Clavet, P.A.; Williams, G.H. J. Chem. Soc. (C) 1969, 146-151. Ahlbrecht, H.; Vonderheid, C. Chem. Ber. 1975, 108, 2300-2311.
10. b: Deady, L.W.; Finlayson, W.L. Synth. Commun. 1980, 10, 947-950.
11. c: Katritzky, A.R.; Thind, S.S. J. Chem. Soc., Perldn Trans. 1 1980, 1895-1900.
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14. e: Ramsey, V.G.; Baldwin, W.E.; Tipson, R.S. J. Am. Chem. Soc. 1947, 69, 67-70. Schultz, O.-E.; Amschler, U. Justus Liebigs Ann. Chem. 1970, 740, 192-195.
15. f: Kutney, J.P.; Noda, M.; Lewis, N.G.; Monteiro, B.; Mostowicz, D. and Worth, B.R. Heterocycles 1981, 16, 1469-1472. Tolmachev, A.A.; Babichenko, L.N.; Sheinkman, A.K. Ukr. Khim. Zh. 1990, 9, 1007-1008.
16. f: Kutney, J.P.; Noda, M.; Lewis, N.G.; Monteiro, B.; Mostowicz, D. and Worth, B.R. Heterocycles 1981, 16, 1469-1472. Tolmachev, A.A.; Babichenko, L.N.; Sheinkman, A.K. Ukr. Khim. Zh. 1990, 9, 1007-1008.
17. g: Blokhin, A.V.; Tyurekhodzhaeva, M.A.; Bazhenov, D.V.; Bobrovskii, S.I.; Bundel, Yu.G. Khim. Geterotsikl. Soedin 1990, 9, 1226-1229.
18. Szantay, C.; Blasko, G.; Honty, K.; Dornyei, G. The Alkaloids; Academic: Orlando 1986, 27, 131-268.
19. Compounds 3a-i as well as compound 1, were prepared according to a classical route by heating them in ethanol with a large excess (10 eq) of iodomethane during 3 days (Godard, A.; Lamour, P.; Ribéreau, P.; Quéguiner, G. Tetrahedron Lett. 1995, 51, 3247-3264).
20. Typical procedure: anhydrous boiling (215°C) pyridinium chloride (20g) is added to the required N-methylpyridinium compound (2 mmoles), and the resulting mixture is refluxed for 10 minutes. The resulting hot solution is poured onto a mixture of ice and concentrated ammonia. Extraction of the aqueous layer by ethyl acetate, drying over magnesium sulfate and solvent removal give the corresponding pyridine derivatives as pure material.
21. Katritzky, A.R. Tetrahedron 1980, 36, 679-699 and references cited therein.
22. 2I (310.1) C 46.5%; H 3.6%; N 9.0%. Found C 46.5%; H 3.5%; N 9.1%.