Expedient synthesis of 1,2,3-triazole-fused tetracyclic compounds by intramolecular Huisgen ('click') reactions on carbohydrate-derived azido-alkynes

Tetrahedron Letters

Volumn 46, Issue 27, 2005, Pages 4585-4588

  Hotha, Srinivas ^a   Anegundi, Ramakrishna I ^a   Natu, Arvind A ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Carbohydrates; Click chemistry; Cycloaddition; Diversity oriented synthesis; Huisgen reaction

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ALKYNE DERIVATIVE; CARBOHYDRATE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; HUISGEN REACTION;

EID: 20344369760     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.012     Document Type: Article

References (14)

1. R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E. De Clercq, C.-F. Perno, A. Karlsson, J. Balzarini, and M.J. Camarasa J. Med. Chem. 37 1994 4185 4194
2. D.R. Buckle, C.J.M. Rockell, H. Smith, and B.A. Spicer J. Med. Chem. 29 1986 2269 2277
3. 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. Stper, and B.H. Yagi J. Med. Chem. 43 2000 953 970
4. H. Wamhoff A.R. Katritzky C.W. Rees Comprehensive Heterocyclic Chemistry Vol. 5 1984 Pergamon Oxford 669 732
5. R. Huisgen A. Padwa 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley New York
6. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
7. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128 1137
8. A. Hasegawa, and M. Kisho Carbohydr. Res. 79 1980 265 270
9. 2. In the cases of products 9 and 15 which did not result in a solid, the reaction mixture was concentrated in vacuo to give a crude residue, which was purified by passing through a pad of silica gel
10. S. Tripathi, K. Singha, B. Achari, and S.B. Mandal Tetrahedron 60 2004 4959 4965
11. 2 = 0.0306. Crystallographic data has been deposited for compound 3 with the Cambridge Crystallographic Data Centre, [CCDC 264130]. Copies of the data can be obtained free of charge via ww.ccdc.cam.ac.uk/conts/retrieving.html or CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk)
12. R. Somanthan, and L.H. Helberg Org. Prep. Proced. Int. 16 1984 388 391
13. See Supplementary data
14. 4 as C, 52.17%; H, 5.97%; N, 16.59%. Found: C, 52.44%; H, 5.90%; N, 16.34%