The 4-methoxybenzyl (PMB) function as a versatile protecting group in the synthesis of N-unsubstituted pyrazolones

Heterocycles

Volumn 63, Issue 11, 2004, Pages 2537-2555

  Eller, Gernot A ^a   Holzer, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 METHOXYBENZYL) 2,4 DIHYDRO 3H PYRAZOL 3 ONE; 4 ACYL 5 HYDROXY 1 4 METHOXYBENZYLHYDRAZINE 1H PYRAZOLE DERIVATIVE; 4 BENZYLIDENE DERIVATIVE; 4 DIMETHYLAMINOMETHYLENE; 4 METHOXYBENZYL GROUP; 4 METHOXYBENZYLHYDRAZINE; BENZALDEHYDE; BENZYLIDENE DERIVATIVE; CALCIUM HYDROXIDE; CARBENOID; CARBOXYLIC ACID; DIOXANE; ETHOXYMETHYLENEMALONIC ACID DIETHYL ESTER; FUNCTIONAL GROUP; HYDRAZINE DERIVATIVE; MALONIC ACID DERIVATIVE; N,N DIMETHYLFORMAMIDE; NITROGEN; PYRAZOLE; PYRAZOLE DERIVATIVE; PYRAZOLONE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; NITROGEN NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 9444240273     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-04-10190     Document Type: Article

References (38)

1. J. Elguero, 'Comprehensive Heterocyclic Chemistry: Pyrazoles and their Benzo Derivatives', Vol. 5; ed. by A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, pp. 167-303.
2. K. Kirschke, 'Houben-Weyl: Methoden der Organischen Chemie', Vol. E8b, ed. by E. Schaumann, Thieme Verlag, Stuttgart - New York, 1994, pp. 399-763.
3. J. Elguero, C. Marzin, and A. R. Katritzky, 'Advances in Heterocyclic Chemistry, Suppl. 1: The Tautomerism of Heterocycles', Academic Press, New York, 1976, pp. 313-336.
4. V. I. Minkin, A. D. Garnovskii, J. Elguero, A. R. Katritzky, and O. V. Denisko, 'The tautomerism of heterocycles: Five-membered rings with two or more heteroatoms', Advances in Heterocyclic Chemistry, 2000, 76, 157-323; and references cited therein.
5. H. Dorn, J. Prakt. Chem., 1973, 315, 382.
6. L. N. Kurkovskaya, N. N. Shapet'ko, A. S. Vitvitskaya, and A. Y. Kvitko, J. Org. Chem. USSR (Engl. Transl.), 1977, 13, 1618; original paper: Zh. Org. Khim., 1977, 13, 1750.
7. L. N. Kurkovskaya, N. N. Shapet'ko, A. S. Vitvitskaya, and A. Y. Kvitko, J. Org. Chem. USSR (Engl. Transl.), 1977, 13, 1618; original paper: Zh. Org. Khim., 1977, 13, 1750.
8. W. Holzer, K. Mereiter, and B. Plagens, Heterocycles, 1999, 50, 799.
9. W. Holzer and I. Krca, Heterocycles, 2003, 60, 2323.
10. W. Holzer and L. Hallak, Heterocycles, 2004, 63, 1311.
11. W. Holzer, C. Kautsch, C. Laggner, R. M. Claramunt, M. Pérez-Torralba, I. Alkorta, and J. Elguero, Tetrahedron, 2004, 60, 6791.
12. H. Wamhoff, D. Schramm, and F. Korte, Synthesis, 1971, 216.
13. B. S. Jensen, Acta Chem. Scand., 1959, 13, 1668.
14. M. Begtrup, Bull. Soc. Chim. Belg., 1988, 97, 573.
15. M. Begtrup, P. Larsen, and P. Vedsø, Acta Chem. Scand., 1992, 46, 972.
16. A. Werner, A. Sánchez-Migallón, A. Fruchier, J. Elguero, C. Fernández-Castano, and C. Foces-Foces, Tetrahedron, 1995, 51, 4779.
17. C. Subramanyam, Synth. Commun., 1995, 25, 761.
18. J. Eskildsen, J. Kristensen, P. Vedsø, and M. Begtrup, J. Org. Chem., 2001, 66, 8654.
19. I. A. Zavialov, V. H. Dahanukar, H. Nguyen, C. Orr, and D. R. Andrews, Org. Lett., 2004, 6, 2237.
20. D. R. Buckle and C. J. M. Rockell, J. Chem. Soc., Perkin Trans. 1, 1982, 627.
21. A. Michaelis, Liebigs Ann. Chem., 1911, 385, 1.
22. T. Curtius and F. Schneiders, J. Prakt. Chem., 1912, 85, 37.
23. W. Holzer, R. M. Claramunt, M. Pérez-Torralba, D. Guggi, and T. H. Brehmer, J. Org. Chem., 2003, 68, 7943.
24. D. G. Davis and A. Bax, J. Am. Chem. Soc., 1985, 107, 7197.
25. S. K. Sarkar and A. Bax, J. Magn. Reson., 1985, 62, 109.
26. A. Bax, J. Magn. Reson., 1984, 57, 314.
27. T. Jippo, O. Kamo, and N. Nagayama, J. Magn. Reson., 1986, 66, 344.
28. G. A. Morris and R. Freeman, J. Am. Chem. Soc., 1979, 101, 760.
29. D. P. Burum and R. R. Ernst, J. Magn. Reson., 1980, 39, 163.
30. L. E. Kay, P. Keifer, and T. Saarinen, J. Am. Chem. Soc., 1992, 114, 10663.
31. A. G. Palmer III, J. Cavanagh, P. E. Wright, and M. Rance, J. Magn. Reson., 1991, 93, 151.
32. J. Schleucher, M. Schwendinger, M. Sattler, P. Schmidt, O. Schedletzky, S. J. Glaser, O. W. Sørensen, and C. Griesinger, J. Biomol. NMR, 1994, 4, 301.
33. W. Willker, D. Leibfritz, R. Kerssebaum, and W. Bermel, Magn. Reson. Chem., 1993, 31, 287.
34. W. Holzer and G. A. Eller, manuscript in preparation.
35. ACD/Name, version 8.05, Advanced Chemistry Development, Inc., Toronto ON, Canada, www.acdlabs.com, 2004.
36. J. I. Finneman and J. C. Fishbein, J. Am. Chem. Soc., 1995, 117, 4228.
37. M. K. Pedersen, I. T. Birk, A. B. Orth, B. K. Singh, B. Tecle, V. Kameswaran, and S. S. Szuces, 2002, WO 2002006512 (Chem. Abstr., 2002, 136, 97843).
38. S. Nishijo and C. Fukuda, 1953, JP 28001588 (Chem. Abstr., 1954, 48, 68274).