Synthesis and structural characterization of 1- and 2-substituted indazoles: Ester and carboxylic acid derivatives

Molecules

Volumn 11, Issue 11, 2006, Pages 867-889

  Teixeira, Fátima C ^a   Ramos, Hélène ^a   Antunes, Inês F ^a   Curto, M João M ^a   Duarte, M Teresa ^b   Bento, Isabel ^c  

^a INETI   (Portugal)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^c INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

Author keywords

Indazole; N 1 and N 2 isomers; Spectroscopic characterization; X ray diffraction studies

Indexed keywords

ACETIC ACID; CARBON; CARBOXYLIC ACID; ESTER; INDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ACETIC ACID; CARBON ISOTOPES; CARBOXYLIC ACIDS; ESTERS; HYDROGEN BONDING; INDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 33845402420     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/11110867     Document Type: Article

References (57)

1. (a) Elguero, J. In Comprehensive Heterocyclic Chemistry: Pyrazoles and their benzo derivatives; Katritzky, A. R.; Rees, C. W., Ed.; Pergamon Press: Oxford, 1984; Vol. 5, pp. 167-303;
2. (b) Elguero, J. In Comprehensive Heterocyclic Chemistry II: Pyrazoles, Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 3, pp. 1-75.
3. (a) Stadlbauer, W. In Houben-Weyl, Methoden der Organischen Chemie: Indazole (Benzopyrazole); Schaumann, E.; Ed.; Georg-Thieme-Verlag Stuttgart: New York, 1994; Vol. E8b, Hetarenes III/2, pp. 764-864;
4. (b) Stadlbauer W. In Science of Synthesis: Indazoles, Neier, R., Ed.; Georg-Thieme-Verlag Stuttgart: New York, 2002; Vol. 2.12.4 (Hetarenes), pp. 227-324.
5. Ikeda, Y.; Takano, N.; Matsushita, H.; Shiraki, Y.; Koide, T.; Nagashima, R.; Fujimura, Y.; Shindo, M.; Suzuki, S.; Iwasaki, T. Arzneim.-Forsch. 1979, 29, 511-520.
6. Picciola, G.; Ravenna, F.; Carenini, G.; Gentili, P.; Riva, M. Farmaco Ed. Sci. 1981, 36, 1037-1056.
7. The Merck Index, 12th edition; Budavari, S., Ed,; Merck & Co.: Rahway, New Jersey, 1996.
8. Mosti, L.; Menozzi, G.; Fossa, P.; Schenone, P.; Lampa, E.; Parrillo, C.; D'Amisco, M.; Rossi, F. Farmaco 1992, 47, 567-584.
9. Andronati, S.; Sava, V.; Makan, S.; Kolodeev, G. Pharmazie 1999, 54, 99-101.
10. Kharitonov, V. G.; Sharma, V. S.; Magde, D.; Koesling, D. Biochemistry 1999, 38, 10699-10706.
11. (a) Rodgers, J. D.; Johnson, B. L.; Wang, H.; Greenberg, R. A.; Erickson-Viitanen, S.; Klabe, R. M.; Cordova, B. C.; Rayner, M. M.; Lam, G. N.; Chang, C.-H. Bioorg. Med. Chem. Lett. 1996, 6, 2919-2924;
12. (b) Sun, J.-H.; Teleha, C. A.; Yan, J.-S.; Rodgers; J. D.; Nugiel, D. A. J. Org. Chem. 1997, 62, 5627-5629.
13. (a) Morie, T.; Harada, H.; Kato, S. Synth. Commun. 1997, 27, 559-566;
14. (b) Bermudez, J.; Fake, C. S.; Joiner, G. F.; Joiner, K. A.; King, F. D.; Miner, W. D.; Sanger, G. J. J. Med. Chem. 1990, 33, 1924-1929.
15. Nofre, C.; Tinti, J. M.; Quar, F. FR Patent 26099603, 1988.
16. Catalán, J.; Valle, J. C.; Claramunt, R. M.; Boyer, G.; Laynez, J.; Gómez, J.; Jiménez, P.; Tomás, F.; Elguero, J. J. Phys. Chem. 1994, 41, 10606-10612.
17. (a) Escande, A.; Lapasset, J.; Faure, R.; Vicenta, E.-J.; Elguero, J. Tetrahedron 1974, 30, 2903-2909;
18. (b) Faure, R.; Vicent, E. J.; Elguero, J. Heterocycles 1983, 20, 1713-1716;
19. (c) Catalán, J.; Paz, J. L. G.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1996, 57-60;
20. (d) Foces-Foces, C.; Hager, O.; Jagerovic, N.; Jimeno, M. L.; Elguero, J. Chem. Eur. J. 1997, 3, 121-126.
21. (a) Black, P. J.; Heffernan, M. L. Aust. J. Chem. 1963, 14, 1051-1055;
22. (b) Jaffari, G. A.; Nunn, A. J. J. Chem. Soc., Perkin Trans. 1 1973, 2371-2374;
23. (c) Palmer, M. H.; Findlay, R. H.; Kennedy, S. M. F.; McIntyre, P. S. J. Chem. Soc., Perkin Trans. 2 1975, 1695-1700;
24. (d) Brown, F. J.; Yee, Y. K.; Cronk, L. A.; Hebbel, K. C.; Krell, R. D.; Snyder, D. W. J. Med. Chem. 1990, 33, 1771-1781.
25. Yamazaki, T.; Baum, G.; Shechter, H. Tetrahedon Lett. 1974, 49-50, 4421-4424.
26. Begtrup, M.; Claramunt, R. M.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1978, 99-104.
27. Cheung, M.; Boloor, A.; Stafford, J. A. J. Org. Chem. 2003, 68, 4093-4095.
28. (a) Elguero, J.; Fruchier, A.; Jacquier, R. Bull. Soc. Chim. Fr. 1966, 2075-2084;
29. (b) Buu-Hoï, N. P.; Hoeffinger, J.-P.; Jacquignon, P. Bull. Soc. Chim. Fr. 1967, 2019-2020;
30. (c) Elguero, J.; Fruchier, A.; Jacquier, R. Bull. Soc. Chim. Fr. 1969, 2064-2076;
31. (d) Elguero, J.; Fruchier, A.; Jacquier, R.; Scheidegger, U. J. Chim. Phys. Phys.-Chim. Biol 1971., 68, 1113-1121;
32. (e) Palmer, M. H.; Findlay, R. H.; Kennedy, S. M. F.; McIntyre, P. S. J. Chem. Soc., Perkin Trans. 2 1975, 1695-1700;
33. (f) Bouchet, P.; Fruchier, A.; Joncheray, G.; Elguero, J. Org. Magn. Reson. 1977, 9, 716-718;
34. (g) Stefaniak, L. Org. Magn. Reson. 1978, 11, 385-389;
35. (h) Elguero, J.; Fruchier, A.; Tjiou, E. M.; Trofimenko, S. Khim. Geterotsikl. Soedin. 1995, 9, 1159-1179.
36. Kingsbury, W. D.; Gyurik, R. J.; Theodorides, V. J.; Parish, R. C.; Gallagher, Jr., G. J. Med. Chem. 1976, 19, 839-840.
37. Auwers, K. V.; Allardt, H. G. Ber. 1926, 59, 95-100.
38. Levy, D. E.; Smyth M. S.; Scarborough, R. M. WO Patent 03/022214, 2003.
39. Costa, M. R. G.; Curto, M. J. M.; Davies, S. G.; Duarte, M. T.; Resende, C.; Teixeira, F. C. J. Organomet. Chem. 2000, 604, 157-169.
40. Farrugia, L. J. J. Appl. Cryst. 1997, 30, 565 (based on ORTEP-III (v.1.0.3.) by Johnson C. K.; Burnett, M. N.).
41. (a) Allen, F. H. Acta Cryst. 2002, B58, 380-388;
42. (b) Bruno, I. J.; Cole, J. C.; Edginton, P. R.; Kessler, M.; Macrae, C. F.; MacCabe, P. M.; Pearson, J.; Taylor, R. Acta Cryst. 2002, B58, 389-397.
43. (a) Ferguson, G.; Gallagher; J. F.; McAlees, A. J. Acta Cryst. 1995, C51, 454-458;
44. (b) Bernstein, J.; Davies, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555-1573;
45. (c) Allen, F. H.; Motherwell, W. D. S.; Raithby, P. R.; Shields, G. P.; Taylor, R. New J. Chem. 1999, 25-34.
46. (a) Foces-Foces, C. Acta Cryst. 2005, E61, o337-o339;
47. (b) Hager, O.; Foces-Foces, C.; Jagerovic, N.; Elguero, J.; Trofimenko, S. Acta Cryst. 1996, C52, 2894-2896.
48. (a) Foces-Foces, C.; Echevarría, A.; Jagerovic, N.; Alkorta, I.; Elguero, J.; Langer, U.; Klein, O.; Minguet-Bomvehí, M.; Limbach, H.-H. J. Am. Chem. Soc. 2001, 123, 7898-7906;
49. (b) Foces-Foces, C.; Alkorta, I.; Elguero, J. Acta Cryst. 2000, B56, 1018-1028;
50. (c) Ching, N.; Pan, L.; Huang, X.; Li, J. Acta Cryst. 2000, C56, 1124-1125.
51. Boa, A. N.; Crane, J. D. Acta Cryst. 2004, E60, o966-o967.
52. Aakeröy, C. B.; Salmon, D. J. Cryst. Eng. Comm. 2005, 7, 439-448.
53. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2nd Edition; Pergamon Press: Oxford, 1980.
54. Konoike, T.; Araki, Y.; Hayashi, T.; Sakurai, K.; Tozyo, T. EP Patent 628569, 1994.
55. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Cryst. 1999, 32, 115-119.
56. Sheldrick, G. M. SHELXL, A Program for Refining Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
57. Farrugia, L. J. J. Appl. Cryst. 1999, 32, 837-837.