Synthesis of triazole-functionalized tetrahydroindazolones by 1,3-dipolar cycloadditions between azides and alkynes

Tetrahedron Letters

Volumn 50, Issue 25, 2009, Pages 3046-3049

  Strakova, Inta ^a   Turks, Maris ^a   Strakovs, Andris ^a  

^a RIGA TECHNICAL UNIVERSITY   (Latvia)

Author keywords

Azides; Huisgen 1,3 dipolar cycloaddition; Tetrahydroindazolones; Triazoles

Indexed keywords

ALKYNE DERIVATIVE; AZIDE; INDAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; TETRAHYDROINDAZOLONE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; NUCLEAR OVERHAUSER EFFECT; OLIGOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 65449158717     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.009     Document Type: Article

References (44)

1. Wolf, A. D. Ger. Offen. DE2646628, 1977; Chem. Abstr. 1977, 87, 68350.
2. Wolf, A. D. U.S. Patent 4124373, 1978; Chem. Abstr. 1979, 90, 152175.
3. Lyga J.W., Patera R.M., Plummer M.J., Halling B.P., and Yuhas D.A. Pestic. Sci. 42 (1994) 29-36
4. Heistracher, E.; Rueb, L.; von dem Bussche-Huennefeld, E.; Hamprecht, G.; Klintz, R.; Schaefer, P.; Westphalen, K.-O.; Gerber, M.; Walter, H. Int. Pat. Appl. WO9606830, 1996; Chem. Abstr. 1996, 125, 86636.
5. Nagakura M., Ota T., Shimidzu N., Kawamura K., Eto Y., and Wada Y. J. Med. Chem. 22 (1979) 48-52
6. McQuaid L.A., Latz J.E., Clemens J.A., Fuller R.W., Wong D.T., and Mason N.R. J. Med. Chem. 32 (1989) 2388-2396
7. Connolly P.J., Westin C.D., Laughey D.A., and Minor L.K. J. Med. Chem. 36 (1993) 3674-3685
8. Connolly, P. J.; Wachter, M. P. U.S. Patent 5134155, 1992; Chem. Abstr. 1992, 117, 212493.
9. Connolly, P. J.; Wachter, M. P. U.S. Patent 5387693, 1995; Chem. Abstr. 1995, 122, 265369.
10. Pevarello, P.; Villa, M.; Varasi, M.; Isacchi, A. Int. Pat. Appl. WO0069846, 2000; Chem. Abstr. 2000, 133, 362767.
11. Bryant, H. J.; Chambers, M. S. Int. Pat. Appl. WO0040565, 2000; Chem. Abstr. 2000, 133, 105033.
12. Maynard, G.; Albaugh, P.; Rachwal, S.; Gustavson, L. M. Int. Pat. Appl. WO0220492, 2002; Chem. Abstr. 2002, 136, 247578.
13. Schiemann, K.; Finsinger, D.; Zenke, F. Int. Pat. Appl. WO2008080455, 2008; Chem. Abstr. 2008, 149, 153070.
14. Xia, M.; Zhang, T.; Wang, Y.; Xing, G. Int. Pat. Appl. WO2006133634, 2006; Chem. Abstr. 2007, 146, 62711.
15. Huang, K. H.; Ommen, A. J.; Barta, T. E.; Hughes, P. F.; Veal, J.; Ma, W.; Smith, E. D.; Woodward, A. R.; McCall, W. S. Int. Pat. Appl. WO2008130879, 2008; Chem. Abstr. 2008, 149, 534224.
16. Prasanna S., Manivannan E., and Chaturvedi S.C. Arch. Pharm. Pharm. Med. Chem. 337 (2004) 440-444
17. Prasanna S., Manivannan E., and Chaturvedi S.C. Bioorg. Med. Chem. Lett. 15 (2005) 2097-2102
18. Wiener J.J.M., Gomez L., Venkatesan H., Santillian A., Allison B.D., Schwarz K.K., Shinde S., Tang L., Hack M.D., Morrow B.J., Motley S.T., Goldschmidt R.M., Shaw K.J., Jones T.K., and Grice C.A. Bioorg. Med. Chem. Lett. 17 (2007) 2718-2722
19. Gomez L., Hack M.D., Wu J., Wiener J.J.M., Venkatesan H., Santillian A., Pippel D.J., Mani N., Morrow B.J., Motley S.T., Shaw K.J., Wolin R., Grice C.A., and Jones T.K. Bioorg. Med. Chem. Lett. 17 (2007) 2723-2727
20. Peterlin-Mašič L., Mlinšek G., Šolmajer T., Trampuš-Bakija A., Stegnar M., and Kikelj D. Bioorg. Med. Chem. Lett. 13 (2003) 789-794
21. Corbera J., Vano D., Martinez D., Vela J.M., Zamanillo D., Dordal A., Andreu F., Hernandez E., Perez R., Escriche M., Salgaro L., Yeste S., Serafini M.T., Pascual R., Alegre J., Calvet M.C., Cano N., Carro M., Buschmann H., and Holenz J. Chem. Med. Chem. 1 (2006) 140-154
22. Lyga J.W., Henrie R.N., Meier G.A., Creekmore W., and Patera R.M. Magn. Reson. Chem. 31 (1993) 323-328
23. For a recent review, see:. Delyatitskaya L., and Strakovs A. Latv. J. Chem. (2002) 129-151
24. For a recent example, see:. Nakhai A., and Bergman J. Tetrahedron 65 (2009) 2298-2306
25. Meegalla S.K., Doller D., Liu R., Sha D., Soll R.M., and Dhanoa D.S. Tetrahedron Lett. 43 (2002) 8639-8642
26. Middleton R.J., Mellor S.L., Chhabra S.R., Bycroft B.W., and Chang W.C. Tetrahedron Lett. 45 (2004) 1237-1242
27. Kashima C. Heterocycles 60 (2003) 959-987
28. Molteni V., Hamilton M.M., Mao L., Crane C.M., Termin A.P., and Wilson D.M. Synthesis (2002) 1669-1674
29. Claramunt R.M., Lopez C., Perez-Medina C., Pinilla E., Torres M.R., and Elguerro J. Tetrahedron 62 (2006) 11704-11713 and references therein
30. Strakov A.Ya., Gudrinietse E.Yu., and Strakova I.A. Chem. Heterocycl. Comp. 24 (1988) 585-599
31. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
32. For a recent review of the mechanistic and synthetic aspects of Cu(I)-catalyzed alkyne-azide couplings, including the choice of catalysts and the regiochemical outcomes of the reactions, see:. Bock V.D., Hiemstra H., and van Maarseveen J.H. Eur. J. Org. Chem. (2006) 51-68 and references cited therein
33. For a recent example, see example:. Kamal A., Shankaraiah N., Devaiah V., Laxma Reddy K., Juvekar A., Sen S., Kurian N., and Zingde S. Bioorg. Med. Chem. Lett. 18 (2008) 1468-1473 and references cited therein
34. Strakov A.Ya., Strakova I.A., Zicane D.R., and Gudriniece E.Y. Dokl. Akad. Nauk SSSR Ser. Khim. 210 (1973) 1352-1354 Doklady Chem. 1973, 210, 518-520
35. Strakov A.Ya., Strakova I.A., Zicane D.R., and Gudriniece E.Y. Izv. Akad. Nauk LatvSSR, Ser. Khim. (1973) 737-740 Chem. Abstr. 1974, 80, 82797d
36. Strakov A.Ya., Strakova I.A., Zicane D.R., and Gudriniece E.Y. Izv. Akad. Nauk LatvSSR, Ser. Khim. (1974) 68-71 Chem. Abstr. 1974, 80, 133332h
37. Strakova I.A., Strakov A.Ya., and Petrova M.V. Latv. J. Chem. (1994) 733-737
38. Strakova I.A., Strakov A.Y., and Petrova M.V. Chem. Heterocycl. Compd. 31 (1995) 303-306
39. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
40. For a recent application, see:. Quader S., Boyd S.E., Jenkins I.D., and Houston T.A. J. Org. Chem. 72 (2007) 1962-1979
41. For a recent application, see:. Punidha S., Sinha J., Kumar A., and Ravikanth M. J. Org. Chem. 73 (2008) 323-326
42. Crystallographic data for 4j have been deposited with the Cambridge Crystallographic Data Centre as a Supplementary Publication No. CCDC 719565.
43. Crystallographic data for 4m have been deposited with the Cambridge Crystallographic Data Centre as a Supplementary Publication No. CCDC 719566.
44. For experimental procedures and characterization of products, see Supplementary data.