Regioselectivity in the formation of norbornene-fused pyrazoles: Preparation of 1-substituted derivatives of 4,5,6,7-tetrahydro-1H-4,7- methanoindazole

Tetrahedron

Volumn 62, Issue 14, 2006, Pages 3362-3369

  Fernández, Franco ^a   Caamaño, Olga ^a   García, Marcos Daniel ^a   Alkorta, Ibon ^b   Elguero, José ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

Norbornene fused pyrazoles; Pyrazolidines; Pyrazolines; Regioselectivity; Stabilizing effect

Indexed keywords

4,5,6,7 TETRAHYDRO 1H 4,7 METHANOINDAZOLE; INDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY ANALYSIS; X RAY DIFFRACTION;

EID: 33644889440     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.059     Document Type: Article

References (26)

1. R. Fusco R.H. Wiley Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles, and Condensed Rings 1967 Wiley New York
2. K. Schofield, M.R. Grimmett, and B.T.R. Keene The Azoles 1976 Cambridge University Cambridge
3. J. Elguero A.R. Katritzky C.W. Rees Comprehensive Heterocyclic Chemistry Vol. 5 1984 Pergamon New York 167 303
4. J. Elguero A.R. Katritzky C.W. Rees E.F.W. Scriven Comprehensive Heterocyclic Chemistry II Vol. 3 1996 Pergamon New York 1 75
5. K. Kirsche E. Schaumann Methoden der Organische Chemie (Houben-Weyl) Vol. 3 1994 Georg Thieme Stuttgart 399 763 Part 2
6. J. Elguero, A. Fruchier, N. Jagerovic, and A. Werner Org. Prep. Proc. Int. 27 1995 33 74
7. J. Elguero, I. Rozas, S.P. Singh, D. Kumar, H. Batra, and R. Naithani Can. J. Chem. 78 2000 1109 1120 and references therein
8. T. Norris, R. Colon-Cruz, and D.H.B. Ripin Org. Biomol. Chem. 3 2005 1844 1849
9. J. Elguero, and G.I. Yranzo J. Chem. Res. Synopses 1990 120 121
10. N.Z. Zefirov, S.I. Kozhushkov, T.S. Kuznetsova, B.A. Ershov, and S.I. Selivanov Tetrahedron 42 1986 709 713
11. M.D. García, O. Caamaño, F. Fernández, M.J. Figueira, and G. Gómez Synthesis 2003 2138 2144
12. 11
13. M.D. García, O. Caamaño, F. Fernández, C. López, and E. De Clercq Synthesis 2005 925 932
14. The regioselective formation of 1-substitued derivatives of 4,5,6,7-tetrahydro-4,7-methano-1H-indazole has also been observed in the reaction of camphor derivatives with substituted hydrazines: U. Grošelj, D. Bevk, R. Jakše, S. Rečnik, A. Meden, B. Stanovnik, and J. Svete Tetrahedron 61 2005 3991 3998 and references cited therein
15. W.H. Mills, and I.G. Nixon J. Chem. Soc. 1930 2510 2524
16. A. Martínez, M.L. Jimeno, and J. Elguero A Fruchier New J. Chem. 18 1994 269 277
17. I. Alkorta, and J. Elguero Struct. Chem. 8 1997 189 195
18. Martins, M. A. P.; Zanatta, N.; Bonacorso, H. G.; Rosa, F. A.; Claramunt, R. M.; García, M. A.; Santa María, M.D.; Elguero. J. ARKIVOC, in press.
19. M. Ramos, I. Alkorta, and J. Elguero Tetrahedron 53 1997 1403 1410
20. O. Exner N.B. Chapman J. Shorter The Hammett Equation - the Present Position Advances in Linear Free Energy Relationships 1972 Plenum London 28 29
21. A.K. Saksena, A.T. McPhail, and K.D. Onan Tetrahedron Lett. 22 1981 2067 2070
22. The crystallographic data (excluding structure factors) for the structures of 12 and 13 have been deposited at the Cambridge Crystallographic Data Centre as supplementary publications numbers CCDC 285543 and 285542. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ].
23. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
24. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
25. P.C. Hariharan, and J.A. Pople Theor. Chim. Acta 28 1973 213 222
26. E.L. Eliel, and S.H. Wilen Stereochemistry of Organic Compounds 1994 Wiley New York p 764