An easy synthetic approach to 1,2,3-triazole-fused heterocycles

Tetrahedron

Volumn 66, Issue 46, 2010, Pages 8846-8853

  Fiandanese, Vito ^a   Marchese, Giuseppe ^a   Punzi, Angela ^a   Iannone, Francesco ^a   Rafaschieri, Giacomo G ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Alkynes; Azides; Click chemistry; Cycloaddition; Triazole fused heterocycles

Indexed keywords

1 (2 BROMOBENZYL) 4 (4 METHYLPHENYL) 1H 1,2,3 TRIAZOLE; 1 (2 BROMOBENZYL) 4 (CYCLOPENTYLMETHYL) 1H 1,2,3 TRIAZOLE; 1 (2 BROMOBENZYL) 4 (THIOPHEN 3 YL) 1H 1,2,3 TRIAZOLE; 1 (2 BROMOBENZYL) 4 CYCLOHEXYL 1H 1,2,3 TRIAZOLE; 1 (2 IODOBENZYL) 4 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOLE; 1 (2 IODOBENZYL) 4 OCTYL 1H 1,2,3 TRIAZOLE; 1 (2 IODOBENZYL) 4 PHENYL 1H 1,2,3 TRIAZOLE; 1 (4 METHOXYPHENYL) 5,6 DIHYDRO[1,2,3]TRIAZOLO [5,1 A]ISOQUINOLINE; 1 (4 METHYLPHENYL) 5,6 DIHYDRO[1,2,3]TRIAZOLO [5,1 A]ISOQUINOLINE; 1 (THIOPHEN 3 YL) 5,6 DIHYDRO[1,2,3]TRIAZOLO [5,1 A]ISOQUINOLINE; 1 [2 (2 BROMOPHENYL)ETHYL] 4 (THIOPHEN 3 YL) 1H 1,2,3 TRIAZOLE; 1 [2 (2 BROMOPHENYL)ETHYL] 4 CYCLOHEXYL 1H 1,2,3 TRIAZOLE; 1 [2 (2 IODOPHENYL)ETHYL] 4 OCTYL 1H 1,2,3 TRIAZOLE; 1 [2 (2 IODOPHENYL)ETHYL] 4 PENTYL 1H 1,2,3 TRIAZOLE; 1 [2 (2 IODOPHENYL)ETHYL] 4 PHENYL 1H 1,2,3 TRIAZOLE; 1 CYCLOHEXYL 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE; 1 OCTYL 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE; 1 PENTYL 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE; 1 PHENYL 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE; 1,2,3 TRIAZOLE; 3 (4 METHOXYPHENYL) 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE; 3 (4 METHYLPHENYL) 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE; 3 (CYCLOPENTYLMETHYL) 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE; 3 (THIOPHEN 3 YL) 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE; 3 CYCLOHEXYL 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE; 3 OCTYL 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE; 3 PHENYL 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE; TRIAZOLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; PRIORITY JOURNAL;

EID: 77958182736     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.09.068     Document Type: Article

References (62)

1. T. Lee, M. Cho, S.-Y. Ko, H.-J. Youn, D.J. Baek, W.-J. Cho, C.-Y. Kang, and S. Kim J. Med. Chem. 50 2007 585 589
2. Y. Xia, Z. Fan, J. Yao, Q. Liao, W. Li, F. Qu, and L. Peng Bioorg. Med. Chem. Lett. 16 2006 2693 2698
3. D. Fournier, R. Hoogenboom, and U.S. Schubert Chem. Soc. Rev. 36 2007 1369 1380
4. H. Nandivada, X. Jiang, and J. Lahann Adv. Mater. 19 2007 2197 2208
5. Y.L. Angell, and K. Burgess Chem. Soc. Rev. 36 2007 1369 1380
6. J.E. Moses, and A.D. Moorhouse Chem. Soc. Rev. 36 2007 1249 1262
7. J.-F. Lutz Angew. Chem., Int. Ed. 46 2007 1018 1025
8. M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.E. Emmert, S.A. Garmon, D.R. Graber, K.C. Grega, J.B. Hester, D.K. Hutchinson, J. Morris, R.J. Reischer, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert, and B.H. Yagi J. Med. Chem. 43 2000 953 970
9. D.R. Buckle, C.J.M. Rockell, H. Smith, and B.A. Spicer J. Med. Chem. 29 1986 2262 2267
10. D.R. Buckle, D.J. Outred, C.J.M. Rockell, H. Smith, and B.A. Spicer J. Med. Chem. 26 1983 251 254
11. M.J. Giffin, H. Heaslet, A. Brik, Y.-C. Lin, G. Cauvi, C.-H. Wong, D.E. McRee, J.H. Elder, C.D. Stout, and B.E. Torbett J. Med. Chem. 51 2008 6263 6270
12. R. Huisgen Pure Appl. Chem. 61 1989 613 628
13. R. Huisgen A. Padwa, 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley New York, NY 1 176
14. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596 2599
15. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057 3064
16. Selected reviewes:
17. F. Amblard, J.H. Cho, and R.F. Schinazi Chem. Rev. 109 2009 4207 4220
18. M. Meldal, and C.W. Tornøe Chem. Rev. 108 2008 2952 3015
19. M.V. Gil, M.J. Arévalo, and Ó. López Synthesis 2007 1589 1620
20. D. James, J.-M. Escudier, E. Amigues, J. Schulz, C. Vitry, T. Bordenave, M. Slozek-Pinaud, and E. Fouquet Tetrahedron Lett. 51 2010 1230 1232
21. O.D. Montagnat, G. Lessene, and A.B. Hughes J. Org. Chem. 75 2010 390 398
22. G. Cravotto, V.V. Fokin, D. Garella, A. Binello, L. Boffa, and A. Barge J. Comb. Chem. 12 2010 13 15
23. M. Jurícek, P.H.J. Kouwer, J. Rehák, J. Sly, and A.E. Rowan J. Org. Chem. 74 2009 21 25
24. Y. Xia, Y. Liu, J. Wan, M. Wang, P. Rocchi, F. Qu, J.L. Iovanna, and L. Peng J. Med. Chem. 52 2009 6083 6096
25. J. Broggi, S. Díez-González, J.L. Petersen, S. Berteina-Raboin, S.P. Nolan, and L.A. Agrofoglio Synthesis 2008 141 148
26. P. Li, L. Wang, and Y. Zhang Tetrahedron 64 2008 10825 10830
27. I. Jlalia, H. Elamari, F. Meganem, J. Herscovici, and C. Girard Tetrahedron Lett. 49 2008 6756 6758
28. Z.-X. Wang, and Z.-G. Zhao J. Heterocycl. Chem. 44 2007 89 92
29. S. Chassaing, M. Kumarraja, A.S.S. Sido, P. Pale, and J. Sommer Org. Lett. 9 2007 883 886
30. E.J. Yoo, M. Ahlquist, S.H. Kim, I. Bae, V.V. Fokin, K.B. Sharpless, and S. Chang Angew. Chem., Int. Ed. 46 2007 1730 1733
31. P. Bertrand, and J.P. Gesson J. Org. Chem. 72 2007 3596 3599
32. R.A. Brawn, M. Welzel, J.T. Lowe, and J.S. Panek Org. Lett. 2010 336 339
33. K.C. Majumdar, K. Ray, S. Ganai, and T. Ghosh Synthesis 2010 858 862
34. Y.-Y. Hu, J. Hu, X.-C. Wang, L.-N. Guo, X.-Z. Shu, Y.-N. Niu, and Y.-M. Liang Tetrahedron 66 2010 80 86
35. C. Chowdhury, S. Mukherjee, B. Das, and B. Achari J. Org. Chem. 74 2009 3612 3615
36. C. Chowdhury, A.K. Sasmal, and P.K. Dutta Tetrahedron Lett. 50 2009 2678 2681
37. D.K. Mohapatra, P.K. Maity, M. Shabab, and M.I. Khan Bioorg. Med. Chem. Lett. 19 2009 5241 5245
38. B. Laleu, and M. Lautens J. Org. Chem. 73 2008 9164 9167
39. W.L. Chen, C.L. Su, and X. Huang Synlett 2006 1446 1448
40. F. Dolhem, F.A. Thali, C. Livre, and G. Demailly Eur. J. Org. Chem. 2005 5019 5023
41. C. Chowdhury, S.B. Mandal, and B. Achari Tetrahedron Lett. 46 2005 8531 8534
42. E.A. Shafran, V.A. Bakulev, Y.A. Rozin, and Y.M. Shafran Chem. Heterocycl. Comp. 44 2008 1040 1069
43. Selected reviewes:
44. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, and O. Baudoin Chem. - Eur. J. 16 2010 2654 2672
45. L. Ackermann, R. Vicente, and A.R. Kapdi Angew. Chem., Int. Ed. 48 2009 9792 9826
46. X. Chen, K.M. Engle, D.-H. Wang, and J.-Q. Yu Angew. Chem., Int. Ed. 48 2009 5094 5115
47. O. Daugulis, H.-Q. Do, and D. Shabashov Acc. Chem. Res. 42 2009 1074 1086
48. V. Fiandanese, D. Bottalico, G. Marchese, and A. Punzi Tetrahedron 64 2008 53 60
49. V. Fiandanese, D. Bottalico, G. Marchese, and A. Punzi Tetrahedron 64 2008 7301 7306
50. V. Fiandanese, D. Bottalico, G. Marchese, and A. Punzi Tetrahedron 62 2006 5126 5132
51. V. Fiandanese, D. Bottalico, C. Cardellicchio, G. Marchese, and A. Punzi Tetrahedron 61 2005 4551 4556
52. V. Fiandanese, D. Bottalico, G. Marchese, and A. Punzi J. Organomet. Chem. 690 2005 3004 3008
53. V. Fiandanese, D. Bottalico, G. Marchese, and A. Punzi Tetrahedron 60 2004 11421 11425
54. V. Fiandanese, D. Bottalico, G. Marchese, A. Punzi, M.R. Quarta, and M. Fittipaldi Synthesis 2009 3853 3859
55. V. Fiandanese, D. Bottalico, G. Marchese, A. Punzi, and F. Capuzzolo Tetrahedron 65 2009 10573 10580
56. For a comprehensive review, see: V. Fiandanese, and D. Bottalico Curr. Org. Chem. 13 2009 554 572
57. S. Chuprakov, N. Chernyak, A.S. Dudnik, and V. Gevorgyan Org. Lett. 9 2007 2333 2336
58. K.W. Bentley The Isoquinoline Alkaloids Vol. 1 1998 Hardwood Academic Amsterdam, The Netherlands
59. D. Kletsas, W. Li, Z. Han, and V. Papadopoulos Biochem. Pharmacol. 67 2004 1927 1932
60. U.R. Mach, A.E. Hackling, S. Perachon, S. Ferry, C.G. Wermuth, J.-C. Schwartz, P. Sokoloff, and H. Stark ChemBioChem 5 2004 508 518
61. D.E. Muscarella, K.A. O'Brain, A.T. Lemley, and S.E. Bloom Toxicol. Sci. 74 2003 66 73
62. F. Dzierszinski, A. Coppin, M. Mortuaire, E. Dewally, C. Slomianny, J.-C. Ameisen, F. DeBels, and S. Tomavo Antimicrob. Agents Chemother. 46 2002 3197 3207