Reaction of N-methyl-5-tributylstannyl-4-fluoro-1H-pyrazole and its application to N-methyl-chromeno[2,3-d]pyrazol-9-one synthesis

Journal of Organic Chemistry

Volumn 73, Issue 12, 2008, Pages 4736-4739

  Hanamoto, Takeshi ^a   Hashimoto, Eri ^a   Miura, Masayuki ^a   Furuno, Hiroshi ^b   Inanaga, Junji ^b  

^a SAGA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; COMPLEXATION; KETONES; MICROFLUIDICS; SYNTHESIS (CHEMICAL); TELLURIUM COMPOUNDS; THREE DIMENSIONAL;

1H PYRAZOLE; AMERICAN CHEMICAL SOCIETY (ACS); CHEMICAL EQUATIONS; ELECTROPHILES; GOOD YIELDS; HIGH YIELD; IODOMETHANE; N-METHYLATION; SEQUENTIAL TREATMENTS; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); WIDE-RANGE;

ADDITION REACTIONS;

N METHYL 5 TRIBUTYLSTANNYL 4 FLUORO 1H PYRAZOLE; N METHYLCHROMENO[2,3 D]PYRAZOL 9 ONE; PYRAZOLE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; METHYLATION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MAGNETIC RESONANCE SPECTROSCOPY; PYRAZOLES;

EID: 45249103089     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800431t     Document Type: Article

References (55)

1. Elguero, J. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, UK, 1996; Vol. 5.
2. (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
3. (b) Bégué, J.-P.; Bonnet-Delpon, D. J. Fluorine Chem. 2006, 127, 992.
4. (c) Uneyama, K. Organofluorine Chemistry; Blackwell Publishing: Oxforf, UK, 2006.
5. (d) Chambers, R. D. Fluorine in Organic Chemistry; Blackwell Publishing: Oxford, UK, 2004.
6. (e) Lemal, D. M. J. Org. Chem. 2004, 69, 1.
7. (f) Hiyama, T. Organofluorine Compounds; Springer: Berlin, Germany, 2000.
8. (g) Hudlicky, M.; Pavlath. A. E. Chemistry of Organic Fluorine Compounds II; ACS Monogragh No. 187; American Chemical Society: Washington, DC, 1995.
9. (a) Liu, H.; Huang, X.; Shen, J.; Luo, X.; Li, M.; Xiong, B.; Chen, G.; Shen, L; Yang, Y.; Jiang, H.; Chen, K. J. Med. Chem. 2002, 45, 4816.
10. (b) Price, M. L. P.; Jørgensen, W. L. J. Am. Chem. Soc. 2000, 122, 9455.
11. (c) Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Doctor, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S, A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347.
12. (a) Hanamoto, T.; Koga, Y.; Kido, E.; Kawanami, T.; Furuno, H.; Inanaga, J. Chem. Commun. 2005, 2041.
13. (b) Hanamoto, T.; Suetake, T.; Koga, Y.; Kawanami, T.; Furuno, H.; Inanaga, J. Tetrahedron 2007, 63, 5062.
14. (a) Calle, M.; Calvo, M.; González-Ortega, A.; González-Nogal, A. Tetrahedron 2006, 62, 611.
15. (b) Cottineau, B.; Chenault, J.; Guillaumet, G. Tetrahedron Lett. 2006, 47, 817.
16. (c) Ivachtchenko, A. V.; Kravchenko, D. V.; Zheludeva, V. I.; Pershin, D. G. J. Heterocycl. Chem. 2004, 41, 931.
17. (d) Cottineau, B.; Chenault, J. Synlett 2002, 769.
18. (e) Smith, T. E.; Mourad, M. S.; Velander, A. J. Heterocycles 2002, 57, 1211.
19. (f) Katritzky, A. R.; Wang, M.; Zhang, S.; Voronkov, M. V.; Steel, P. J. J. Org. Chem. 2001, 66, 6787.
20. (g) Azami, H.; Barrett, D.; Tanaka, A.; Sasaki, H.; Matsuda, K.; Sakurai, M.; Terasawa, T.; Shirai, F.; Chiba, T.; Matsumoto, Y.; Tawara, S. Bioorg. Med. Chem. 2001, 9, 961.
21. (h) Calle, M.; Cuadrado, P.; González-Nogal, A. M.; Valero, R. Synthesis 2001, 1949.
22. (i) Okada, I.; Fukuchi, T. J. Pestic Sci. 2000, 25, 310. Chem. Abstr. 2000, 133, 218748.
23. (j) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039.
24. (k) Torrens, A.; Castrillo, J. A.; Redondo, J. Synlett 1999, 765.
25. (l) Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré, A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269.
26. (m) Yamamoto, S.; Sato, T.; Morimoto, K.; Makino, K. J. Heterocycl. Chem. 1991, 28, 1849.
27. (n) Effenberger, F.; Krebs, A. J. Org. Chem. 1984, 49, 4687.
28. Hanamoto, T.; Egashira, M.; Ishizuka, K.; Furuno, H.; Inanaga, J. Tetrahedron 2006, 62, 6332.
29. Harrison, P. G. Chemistry of Tin; Blackie & Son Limited: Glasgow, UK, 1989.
30. For the regiospecific C-5 lithiation of N-1 substituted pyrazoles, see:(a) Hoffmann, M. G. Tetrahedron 1995, 51, 9511.
31. (b) Subramanyam, C. Synth. Commun. 1995, 25, 761.
32. (c) Booker-Milburn, K. I. Synlett 1992, 327.
33. (d) Effenberger, F.; Roos, M.; Ahmad, R.; Krebs, A. Chem. Ber. 1991, 124, 1639.
34. (e) Heinisch, G.; Holzer, W.; Pock, S. J. Chem. Soc. Perkin. Trans. 1 1990, 1829.
35. For some reports on 4-fluoro-3,5-disubstituted-pyrazole derivatives, see: (a) Chanteau, F.; Plantier-Royon, R.; Portella, C. Synlett 2004, 512.
36. (b) Katoch-Rouse, T.; Pavlova, O. A.; Caulder, T.; Hoffman, A. F.; Mukhin, A. G.; Horti, A. G. J. Med. Chem. 2003, 46, 642.
37. (c) Sloop, J. C.; Bumgardner, C. L.; Loehle, W. D. J. Fluorine Chem. 2002, 118, 135.
38. (d) Bouillon, J.-P.; Didier, B.; Dondy, B.; Doussot, P.; Plantier-Royon, R.; Portella, C. Eur. J. Org. Chem. 2001, 187.
39. (e) Dondy, B.; Doussot, P.; Portella, C. Tetrahedron Lett. 1994, 35, 409.
40. (f) Bumgardner, C.; Sloop, J. C. J. Fluorine Chem. 1992, 56, 141.
41. (g) Ishihara, T.; Okada, Y.; Kuroboshi, M.; Shinozaki, T.; Ando, T. Chem. Lett. 1988, 819.
42. (a) Ghosh, T.; Bandyopadhyay, C. J. Heterocycl. Chem. 2006, 43, 1431.
43. (b) Atkinson, P.; Findlay, K. S.; Kielar, F.; Pal, R.; Parker, D.; Poole, R. A.; Puschmann, H.; Richardson, S. L.; Stenson, P. A.; Thompson, A. L.; Yu, J. Org. Biomol. Chem. 2006, 4, 1707.
44. (c) Kristensen, J. L.; Vedsø, P.; Begtrup, M. Tetrahedron 2002, 58, 2397.
45. (d) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349.
46. (e) Rampa, A.; Bisi, A.; Valenti, P.; Recanatini, M.; Cavalli, A.; Andrisano, V.; Cavrini, V.; Fin, L.; Buriani, A.; Giusti, P. J. Med. Chem. 1998, 41, 3976.
47. (f) Ghosh, C. K.; Sahana, S.; Ghosh, C. Indian J. Chem. Sect. B. 1996, 35, 669.
48. (g) Mongin, O.; Rocca, P.; Thomas-dit-Dumont, L.; Trécourt, F.; Marsais, F.; Godard, A.; Quéguiner, G. J. Chem. Soc., Perkin Trans. 1 1995, 2503.
49. (h) Ghosh, C. K.; Bhattacharya, K.; Ghosh, C. Tetrahedron 1994, 50, 4905.
50. (i) Ghosh, C. K.; Bhattacharyya, A.; Ghosh-Dastidar, P. P. Indian J. Chem. Sect. B. 1987, 26, 128.
51. (j) Beelitz, K.; Praefcke, K. Justus Liebigs Ann. Chem. 1979, 1081.
52. (k) Sliwa, H.; Cordonnier, G. J. Heterocycl. Chem. 1977, 14, 169.
53. (l) Villani, F. J.; Magatti, C. V. J. Heterocycl. Chem. 1975, 12, 1239.
54. (m) Villani, F. J.; Hannon, J.; Wefer, E. A.; Mann, T. A.; Morton, J. B. J. Org. Chem. 1975, 40, 1734.
55. 3 under similar conditions.