Synthesis of carbohydrate-derived 1,2,3-triazoles using 1,3-dipolar cycloaddition on a soluble polymer support

Heterocycles

Volumn 51, Issue 8, 1999, Pages 1807-1817

  Freeze, Scott ^a   Norris, Peter ^a  

^a YOUNGSTOWN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

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

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 0033180121     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8518     Document Type: Article

References (11)

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2. E. Williams, Tetrahedron Lett., 1992, 33, 1033.
3. M. Adamczeski, E. Quinoa, and P. Crews, J. Am. Chem. Soc., 1988, 110 1598.
4. A. Padwa, 1,3-Dipolar Cycloaddition Chemistry, John Wiley and Sons, NY, 1984.
5. P. Norris, D. Horton and B.R. Levine, Heterocycles, 1996, 43, 2643.
6. D.J. Gravert and K.D. Janda, Chem. Rev., 1997, 97, 489.
7. J.J. Krepinsky in Modern Methods in Carbohydrate Synthesis, ed. by S.H. Khan , Harwood Academic Press, NY, 1996, p. 194.
8. H. Han, M.M. Wolfe, S. Brenner and K.D. Janda, Proc. Natl. Acad. Sci. USA, 1995, 92, 6419.
9. W.A. Szarek and J.K.N. Jones, Can. J. Chem., 1965, 43, 2345.
10. The reaction with phenyl vinyl sulfoxide affords the parent, unsubstituted, triazole 3 and likely occurs via an initial dipolar cycloaddition followed by an intramolecular elimination of PhSOH from an intermediate triazoline. Similar cycloaddition of phenylvinyl sulfoxide with an adamantyl azide has been reported to yield the aromatic triazole product (T. Sasaki, S. Eguchi, M. Yamaguchi and T. Esaki, J. Org. Chem., 1981, 46, 1800). The single triazole 3 is isolated in 68% yield after workup and column chromatography, however removal of byproducts proved inefficient and 3 is difficult to purify completely by this method. Cycloaddition of 1 with diphenylacetylene to afford triazole 4 is slow, as might be expected with large substituents on the alkyne, and compound 4 is isolated in only 48% yield after flash column chromatography.
11. M. Moore and P. Norris, Tetrahedron Lett., 1998, 39, 7027.