A novel and efficient synthesis of 3-aminomethyl-N-tosyl-indazoles

Tetrahedron

Volumn 66, Issue 46, 2010, Pages 8854-8861

  Kylmälä, Tuula ^a   Hämäläinen, Antti ^a   Kuuloja, Noora ^a   Tois, Jan ^a   Franzén, Robert ^a  

^a TAMPERE UNIVERSITY OF TECHNOLOGY   (Finland)

Author keywords

Anti Selective; Bisindazole; Copper; Cyclization; Indazole

Indexed keywords

3 (PIPERIDIN 1 YLMETHYL) 1 TOSYL 1H INDAZOLE; 3 (TERT BUTYLDIMETHYLSILYLOXY) N,N BIS[(1 TOSYL 1H INDAZOL 3 YL)METHYL)PROPAN 1 AMINE; 3 AMINOMETHYL N TOSYL INDAZOLE; 3 AMINOMETHYL N TOSYL INDAZOLE DERIVATIVE; 4 [(1 TOSYL 1H INDAZOL 3 YL)METHYL)MORPHOLINE; 4 [(5 METHOXY 1 TOSYL 1H INDAZOL 3 YL)METHYL)MORPHOLINE; 4 [(5,6 DIMETHOXY 1 TOSYL 1H INDAZOL 3YL)METHYL)MORPHOLINE; INDAZOLE DERIVATIVE; N [(1 TOSYL 1H INDAZOL 3 YL)METHYL)ANILINE; N' (1 (2 BROMO 4,5 DIMETHOXYPHENYL) 2 MORPHOLINOETHYLIDENE) 4 METHYLBENZENESULFONOHYDRAZIDE; N' (1 (2 BROMOPHENYL 5 METHOXYPHENYL) 2 MORPHOLINOETHYLIDENE) 4 METHYLBENZENESULFONOHYDRAZIDE; N' (1 (2 BROMOPHENYL) 2 (PIPERIDIN 1 YL)ETHYLIDENE) 4 METHYLBENZENESULFONOLHYDRAZIDE; N' (1 (2 BROMOPHENYL) 2 MORPHOLINOETHYLIDENE) 4 METHYLBENZENESULFONOHYDRAZIDE; N' (1 (6 BROMOBENZO[D][1,3]DIOXOL 5 YL) 2 MORPHOLINOETHYLIDENE) 4 METHYLBENZENESULFONOHYDRAZIDE; N'',N'' [(2,2 BENZYLAZANEDIYL)BIS(1 (2 BROMO PHENYL)ETHAN 2 YL 1 YLIDENE)]BIS(4 METHYLBENZENESULFONOHYDRAZIDE); N',N'' (2,2' (3 (TERT BUTYLDIMETHYLSILYLOXY)PROPYLAZANEDIYL)BIS(1 (2 BROMOPHENYL)ETHAN 2 YL 1 YLIDENE))BIS(4 METHYLBENZENESULFONOHYDRAZIDE); N',N'' (2,2' (PHENYLAZANEDIYL)BIS[1 (2 BROMOPHENYL)ETHAN 2 YL 1 YLIDENE)]BIS(4-METHYLBENZENESULFONOHYDRAZIDE); N,N BIS[(1 TOSYL 1H INDAZOL 3 YL)METHYL)ANILINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; PRIORITY JOURNAL; REACTION TIME;

EID: 77958166933     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.09.069     Document Type: Article

References (39)

1. T. Sugaya, Y. Mimura, Y. Shida, Y. Osawa, I. Matsukuma, S. Ikeda, S. Akinaga, M. Morimoto, T. Ashizawa, M. Okabe, H. Ohno, K. Gomi, and M. Kasai J. Med. Chem. 37 1994 1028 1032
2. A. Tanitame, Y. Oyamada, K. Ofuji, Y. Kyoya, K. Suzuki, H. Ito, M. Kawasaki, K. Nagai, M. Wachi, and J. Yamagishi Bioorg. Med. Chem. Lett. 14 2004 2857 2862
3. C.M. McBride, P.A. Renhowe, C. Heise, J.M. Jansen, S. Lapointe, S. Ma, R. Piñeda, J. Vora, M. Wiesmann, and C.M. Shafer Bioorg. Med. Chem. Lett. 16 2006 3595 3599
4. Y.-K. Lee, D.J. Parks, T. Lu, T.V. Thieu, T. Markotan, W. Pan, D.F. McComsey, K.L. Milkiewicz, C.S. Crysler, N. Ninan, M.C. Abad, E.C. Giardino, and B.E. Maryanoff J. Med. Chem. 51 2008 282 297
5. A. Vasudevan, A.J. Souers, J.C. Freeman, M.K. Verzal, J. Gao, M.H. Mulhern, D. Wodka, J.K. Lynch, K.M. Engstrom, S.H. Wagaw, S. Brodjian, B. Dayton, D.H. Falls, E. Bush, M. Brune, R.D. Shapiro, K.C. Marsh, L.E. Hernandez, C.A. Collins, and P.R. Kym Bioorg. Med. Chem. Lett. 15 2005 5293 5297
6. L.H. Jones, G. Allan, O. Barba, C. Burt, R. Corbau, T. Dupont, T. Knöchel, S. Irving, D.S. Middleton, C.E. Mowbray, M. Perros, H. Ringrose, N.A. Swain, R. Webster, M. Westby, and C. Phillips J. Med. Chem. 52 2009 1219 1223
7. A. Schmidt, A. Beutler, and B. Snovydovych Eur. J. Org. Chem. 2008 4073 4095
8. C.M. Counceller, C.C. Eichman, B.C. Wray, and J.P. Stambuli Org. Lett. 10 2008 1021 1023
9. B.R. Henke, C.J. Aquino, L.S. Birkemo, D.K. Croom, R.W. Dougherty Jr., G.N. Ervin, M.K. Grizzle, G.C. Hirst, M.K. James, M.F. Johnson, K.L. Queen, R.G. Sherrill, E.E. Sugg, E.M. Suh, J.W. Szewczyk, R.J. Unwalla, J. Yingling, and T.M. Willson J. Med. Chem. 40 1997 2706 2725
10. H.-J. Boehm, M. Boehringer, D. Bur, H. Gmuender, W. Huber, W. Klaus, D. Kostrewa, H. Kuehne, T. Luebbers, N. Meunier-Keller, and F. Mueller J. Med. Chem. 43 2000 2664 2674
11. F. Crestey, V. Collot, S. Stiebling, and S. Rault Tetrahedron 62 2006 7772 7775
12. H.-C. Zhang, C.K. Derian, P. Andrade-Gordon, W.J. Hoekstra, D.F. McComsey, K.B. White, B.L. Poulter, M.F. Addo, W.-M. Cheung, B.P. Damiano, D. Oksenberg, E.E. Reynolds, A. Pandey, R.M. Scarborough, and B.E. Maryanoff J. Med. Chem. 44 2001 1021 1024
13. G. Büchi, G.C.M. Lee, D. Yang, and S.R. Tannenbaum J. Am. Chem. Soc. 108 1986 4115 4119
14. H.R. Snyder, C.B. Thompson, and R.L. Hinman J. Am. Chem. Soc. 74 1952 2009 2012
15. N.K. Kochetkov, and N.V. Dudykina J. Gen. Chem. USSR 31 1961 189 191
16. F. Crestey, S. Stiebling, R. Legay, V. Collot, and S. Rault Tetrahedron 63 2007 419 428
17. T. Kylmälä, S. Udd, J. Tois, and R. Franzén Tetrahedron Lett. 51 2010 3613 3615
18. T. Tsuji, and E.M. Kosower J. Am. Chem. Soc. 91 1969 3375
19. P.M. Collins, D. Gardiner, S. Kumar, and W.G. Overend J. Chem. Soc., Perkin Trans. 1 1972 2596 2610
20. P.M. Collins, D. Gardiner, S. Kumar, and W.G. Overend J. Chem. Soc., Perkin Trans. 1 1972 2611 2618
21. P.M. Collins, J.R. Hurford, and W.G. Overend J. Chem. Soc., Perkin Trans. 1 1975 2163 2177
22. H. Salaheddine, S.L. Titouani, M. Soufiaoui, and A. Tahdi Tetrahedron Lett. 43 2002 4351 4353
23. G. Matthaiopoulos Chem. Ber. 1898 2396 2399
24. J.H. Smith, J.H. Heidema, E.T. Kaiser, J.B. Wetherington, and J.W. Moncrief J. Am. Chem. Soc. 94 1972 9274 9276
25. J.H. Smith, J.H. Heidema, and E.T. Kaiser J. Am. Chem. Soc. 94 1972 9276 9277
26. J.H. Smith, and E.T. Kaiser J. Org. Chem. 39 1974 728 730
27. K. Wimalasena, and D. Haines J. Org. Chem. 59 1994 6472 6475
28. T.L. Gilchrist Chem. Soc. Rev. 11 1983 53 73
29. I.M. Lyapkalo, and S.L. Ioffe Russ. Chem. Rev. 67 1998 467 484
30. For clarity, we decided to use terms anti/syn instead of E/Z (see picture below). Throughout this article, anti refers to the isomer having the aminomethyl group trans to the hydrazone N-H. In other words, the hydrazone N-H is cis to the aromatic ring.
31. A. Hassner, K.S.K. Murthy, A. Padwa, U. Chiacchio, D.C. Dean, and A.M. Schoffstall J. Org. Chem. 54 1989 5277 5286
32. A. Hassner, R. Maurya, O. Friedman, H.E. Gottlieb, A. Padwa, and D. Austin J. Org. Chem. 58 1993 4539 4546
33. S.E. Denmark, and M.S. Dappen J. Org. Chem. 49 1984 798 806
34. S.E. Denmark, M.S. Dappen, and J.A. Sternberg J. Org. Chem. 49 1984 4741 4743
35. S.E. Denmark, M.S. Dappen, N.L. Sear, and R.T. Jacobs J. Am. Chem. Soc. 112 1990 3466 3474
36. I. Korboukh, P. Kumar, and S.M. Weinreb J. Am. Chem. Soc. 129 2007 10342 10343
37. P. Li, M.M. Majireck, J.A. Witek, and S.M. Weinreb Tetrahedron Lett. 51 2010 2032 2035
38. M.M. Majireck, J.A. Witek, and S.M. Weinreb Tetrahedron Lett. 51 2010 3555 3557
39. S. Udd, R. Jokela, R. Franzén, and J. Tois Tetrahedron Lett. 51 2010 1030 1033