Halogen dance in pyrazole 1-oxides: Synthesis of pyrazolo[3,4-c]quinoline 1-oxides

Tetrahedron

Volumn 58, Issue 38, 2002, Pages 7635-7644

  Eskildsen, Jørgen ^a   Østergaard, Niels ^a,b   Vedsø, Per ^a   Begtrup, Mikael ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b ACADIA PHARMACEUTICALS INC   (United States)

Author keywords

Halogen dance; Metalation; Pyrazole 1 oxides; Pyrazolo 3,4 c quinolines

Indexed keywords

HALOGEN; PYRAZOLE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037119702     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00858-X     Document Type: Article

References (46)

1. For illustrative examples of syntheses and pharmacological data for this structural class see: (a) Baraldi P.G., Borea P.A. Trends Pharmacol. Sci. 21:2000;456-459 (b) Coletta V., Catarzi D., Varano F., Cecchi L., Filacchiono G., Martini C., Trincavelli L., Lucacchini A. J. Med. Chem. 43:2000;3118-3124 (c) Palazzino G., Cecchi L., Melani F., Colotta V., Filacchiono G., Martini C., Lucacchini A. J. Med. Chem. 30:1987;1737-1741 (d) Catarzi D., Coletta V., Varano F., Cecchi L., Filacchiono G., Galli A., Costagli C. Arch. Pharm. Pharm. Med. Chem. 330:1997;383-386 (e) MacLeod A.M., Grimwood S., Barton C., Bristow L., Saywell K.L., Marshall G.R., Ball R.G. J. Med. Chem. 38:1995;2239-2243 (f) Cusmano G., Macaluso G., Vivona N., Ruccia M. Heterocycles. 24:1986;3181-3186 (g) Nagarajan K., Shah R.K. Ind. J. Chem., Sect. B. 31:1992;316-321 (h) Ito K., Maruyama J. J. Heterocycl. Chem. 1988;1681-1687.
2. For illustrative examples of syntheses and pharmacological data for this structural class see: (a) Baraldi P.G., Borea P.A. Trends Pharmacol. Sci. 21:2000;456-459 (b) Coletta V., Catarzi D., Varano F., Cecchi L., Filacchiono G., Martini C., Trincavelli L., Lucacchini A. J. Med. Chem. 43:2000;3118-3124 (c) Palazzino G., Cecchi L., Melani F., Colotta V., Filacchiono G., Martini C., Lucacchini A. J. Med. Chem. 30:1987;1737-1741 (d) Catarzi D., Coletta V., Varano F., Cecchi L., Filacchiono G., Galli A., Costagli C. Arch. Pharm. Pharm. Med. Chem. 330:1997;383-386 (e) MacLeod A.M., Grimwood S., Barton C., Bristow L., Saywell K.L., Marshall G.R., Ball R.G. J. Med. Chem. 38:1995;2239-2243 (f) Cusmano G., Macaluso G., Vivona N., Ruccia M. Heterocycles. 24:1986;3181-3186 (g) Nagarajan K., Shah R.K. Ind. J. Chem., Sect. B. 31:1992;316-321 (h) Ito K., Maruyama J. J. Heterocycl. Chem. 1988;1681-1687.
3. For illustrative examples of syntheses and pharmacological data for this structural class see: (a) Baraldi P.G., Borea P.A. Trends Pharmacol. Sci. 21:2000;456-459 (b) Coletta V., Catarzi D., Varano F., Cecchi L., Filacchiono G., Martini C., Trincavelli L., Lucacchini A. J. Med. Chem. 43:2000;3118-3124 (c) Palazzino G., Cecchi L., Melani F., Colotta V., Filacchiono G., Martini C., Lucacchini A. J. Med. Chem. 30:1987;1737-1741 (d) Catarzi D., Coletta V., Varano F., Cecchi L., Filacchiono G., Galli A., Costagli C. Arch. Pharm. Pharm. Med. Chem. 330:1997;383-386 (e) MacLeod A.M., Grimwood S., Barton C., Bristow L., Saywell K.L., Marshall G.R., Ball R.G. J. Med. Chem. 38:1995;2239-2243 (f) Cusmano G., Macaluso G., Vivona N., Ruccia M. Heterocycles. 24:1986;3181-3186 (g) Nagarajan K., Shah R.K. Ind. J. Chem., Sect. B. 31:1992;316-321 (h) Ito K., Maruyama J. J. Heterocycl. Chem. 1988;1681-1687.
4. For illustrative examples of syntheses and pharmacological data for this structural class see: (a) Baraldi P.G., Borea P.A. Trends Pharmacol. Sci. 21:2000;456-459 (b) Coletta V., Catarzi D., Varano F., Cecchi L., Filacchiono G., Martini C., Trincavelli L., Lucacchini A. J. Med. Chem. 43:2000;3118-3124 (c) Palazzino G., Cecchi L., Melani F., Colotta V., Filacchiono G., Martini C., Lucacchini A. J. Med. Chem. 30:1987;1737-1741 (d) Catarzi D., Coletta V., Varano F., Cecchi L., Filacchiono G., Galli A., Costagli C. Arch. Pharm. Pharm. Med. Chem. 330:1997;383-386 (e) MacLeod A.M., Grimwood S., Barton C., Bristow L., Saywell K.L., Marshall G.R., Ball R.G. J. Med. Chem. 38:1995;2239-2243 (f) Cusmano G., Macaluso G., Vivona N., Ruccia M. Heterocycles. 24:1986;3181-3186 (g) Nagarajan K., Shah R.K. Ind. J. Chem., Sect. B. 31:1992;316-321 (h) Ito K., Maruyama J. J. Heterocycl. Chem. 1988;1681-1687.
5. For illustrative examples of syntheses and pharmacological data for this structural class see: (a) Baraldi P.G., Borea P.A. Trends Pharmacol. Sci. 21:2000;456-459 (b) Coletta V., Catarzi D., Varano F., Cecchi L., Filacchiono G., Martini C., Trincavelli L., Lucacchini A. J. Med. Chem. 43:2000;3118-3124 (c) Palazzino G., Cecchi L., Melani F., Colotta V., Filacchiono G., Martini C., Lucacchini A. J. Med. Chem. 30:1987;1737-1741 (d) Catarzi D., Coletta V., Varano F., Cecchi L., Filacchiono G., Galli A., Costagli C. Arch. Pharm. Pharm. Med. Chem. 330:1997;383-386 (e) MacLeod A.M., Grimwood S., Barton C., Bristow L., Saywell K.L., Marshall G.R., Ball R.G. J. Med. Chem. 38:1995;2239-2243 (f) Cusmano G., Macaluso G., Vivona N., Ruccia M. Heterocycles. 24:1986;3181-3186 (g) Nagarajan K., Shah R.K. Ind. J. Chem., Sect. B. 31:1992;316-321 (h) Ito K., Maruyama J. J. Heterocycl. Chem. 1988;1681-1687.
6. For illustrative examples of syntheses and pharmacological data for this structural class see: (a) Baraldi P.G., Borea P.A. Trends Pharmacol. Sci. 21:2000;456-459 (b) Coletta V., Catarzi D., Varano F., Cecchi L., Filacchiono G., Martini C., Trincavelli L., Lucacchini A. J. Med. Chem. 43:2000;3118-3124 (c) Palazzino G., Cecchi L., Melani F., Colotta V., Filacchiono G., Martini C., Lucacchini A. J. Med. Chem. 30:1987;1737-1741 (d) Catarzi D., Coletta V., Varano F., Cecchi L., Filacchiono G., Galli A., Costagli C. Arch. Pharm. Pharm. Med. Chem. 330:1997;383-386 (e) MacLeod A.M., Grimwood S., Barton C., Bristow L., Saywell K.L., Marshall G.R., Ball R.G. J. Med. Chem. 38:1995;2239-2243 (f) Cusmano G., Macaluso G., Vivona N., Ruccia M. Heterocycles. 24:1986;3181-3186 (g) Nagarajan K., Shah R.K. Ind. J. Chem., Sect. B. 31:1992;316-321 (h) Ito K., Maruyama J. J. Heterocycl. Chem. 1988;1681-1687.
7. For illustrative examples of syntheses and pharmacological data for this structural class see: (a) Baraldi P.G., Borea P.A. Trends Pharmacol. Sci. 21:2000;456-459 (b) Coletta V., Catarzi D., Varano F., Cecchi L., Filacchiono G., Martini C., Trincavelli L., Lucacchini A. J. Med. Chem. 43:2000;3118-3124 (c) Palazzino G., Cecchi L., Melani F., Colotta V., Filacchiono G., Martini C., Lucacchini A. J. Med. Chem. 30:1987;1737-1741 (d) Catarzi D., Coletta V., Varano F., Cecchi L., Filacchiono G., Galli A., Costagli C. Arch. Pharm. Pharm. Med. Chem. 330:1997;383-386 (e) MacLeod A.M., Grimwood S., Barton C., Bristow L., Saywell K.L., Marshall G.R., Ball R.G. J. Med. Chem. 38:1995;2239-2243 (f) Cusmano G., Macaluso G., Vivona N., Ruccia M. Heterocycles. 24:1986;3181-3186 (g) Nagarajan K., Shah R.K. Ind. J. Chem., Sect. B. 31:1992;316-321 (h) Ito K., Maruyama J. J. Heterocycl. Chem. 1988;1681-1687.
8. For illustrative examples of syntheses and pharmacological data for this structural class see: (a) Baraldi P.G., Borea P.A. Trends Pharmacol. Sci. 21:2000;456-459 (b) Coletta V., Catarzi D., Varano F., Cecchi L., Filacchiono G., Martini C., Trincavelli L., Lucacchini A. J. Med. Chem. 43:2000;3118-3124 (c) Palazzino G., Cecchi L., Melani F., Colotta V., Filacchiono G., Martini C., Lucacchini A. J. Med. Chem. 30:1987;1737-1741 (d) Catarzi D., Coletta V., Varano F., Cecchi L., Filacchiono G., Galli A., Costagli C. Arch. Pharm. Pharm. Med. Chem. 330:1997;383-386 (e) MacLeod A.M., Grimwood S., Barton C., Bristow L., Saywell K.L., Marshall G.R., Ball R.G. J. Med. Chem. 38:1995;2239-2243 (f) Cusmano G., Macaluso G., Vivona N., Ruccia M. Heterocycles. 24:1986;3181-3186 (g) Nagarajan K., Shah R.K. Ind. J. Chem., Sect. B. 31:1992;316-321 (h) Ito K., Maruyama J. J. Heterocycl. Chem. 1988;1681-1687.
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27. 2(2THF).
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29. Such reaction types have been referred to in the literature by different designations such as halogen scrambling, halogen migration, halogen isomerization, halogen dance, base catalyzed halogen dance, for reviews see: (a) Frölich J. Prog. Heterocycl. Chem. 6:1994;1-35 (b) Frölich J. Bull. Soc. Chim. Belg. 105:1996;615-634. and references cited herein.
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33. For pioneering investigations into base induced halogen dance see: (a) Bunnet J.F. J. Org. Chem. 5:1972;139-147 (b) Mach M.H., Bunnet J.F. J. Org. Chem. 45:1980;4660-4666. For an elegant example of the use of BCHD in synthesis see: (c) Arzel E., Rocca P., Grellier P., Labaeïd M., Frappier F., Guéritte F., Gaspard C., Marsais F., Godard A., Quéguiner G. J. Med. Chem. 44:2001;949-960.
34. For pioneering investigations into base induced halogen dance see: (a) Bunnet J.F. J. Org. Chem. 5:1972;139-147 (b) Mach M.H., Bunnet J.F. J. Org. Chem. 45:1980;4660-4666. For an elegant example of the use of BCHD in synthesis see: (c) Arzel E., Rocca P., Grellier P., Labaeïd M., Frappier F., Guéritte F., Gaspard C., Marsais F., Godard A., Quéguiner G. J. Med. Chem. 44:2001;949-960.
35. During the course of the present work, the preparation of vicinal dimagnesioimidazole dianions was described and their reaction with electrophiles to give 4,5-disubstitution in 27-71% yield, see: Butz R.H.J., Lindell S.D. J. Org. Chem. 67:2002;2699-2701.
36. 2-signals.
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42. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 184184. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
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