Synthesis of 1,2,3-Triazoles by Cycloadditions of Azides with Enol Ethers

Dario R. Roque; Justin L. Neill; James W. Antoon; Erland P. Stevens

doi:10.1055/s-2005-872116

PAPER

Synthesis of 1,2,3-Triazoles by Cycloadditions of Azides with Enol Ethers

Dario R. Roque, Justin L. Neill, James W. Antoon, Erland P. Stevens*
Department of Chemistry, Davidson College, PO Box 7120, Davidson, NC 28035-7120, USA
Fax: +1(704)8942709; e-Mail: erstevens@davidson.edu;

Abstract

All articles of this category

Abstract

1,2,3-Triazoles were prepared in good to modest yields by cycloaddition of alkyl azides onto enol ethers under solventless conditions. The reaction can access ring-fused triazoles that are unavailable by azide-alkyne cycloadditions and is easily scalable. The 1,2,3-triazole products bear functionality that may be readily derivatized.

Key words

azides - cycloadditions - heterocycles - nitrogen - regioselectivity

Full Text

References

1 Katritzky AR. Rogovoy BV. Chem. Eur. J. 2003, 9: 4586

2 Yokoyama M. Nakao E. Sujuno K. Watanabe S. Togo H. Heterocycles 1990, 31: 1669

3 Caamano O. Figueira MJ. Fernandez R. Garcia MD. Nieto MI. De Clerq E. Balzarini J. Nucleosides, Nucleotides Nucleic Acids 2001, 20: 1137

4 Vicentini CB. Brandolini V. Guarneri M. Farmaco 1992, 47: 1021

5 Chan TR. Hilgraf R. Sharpless KB. Fokin VV. Org. Lett. 2004, 6: 2853

6 Huisgen R. Knorr R. Möbius L. Szeimies G. Chem. Ber. 1965, 98: 4014

7 Rostovstev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 67: 3057

8 Appukkuttan P. Dehaen W. Fokin VV. Van der Eycken E. Org. Lett. 2004, 6: 4223

9 Scarpati R. Sica D. Lionetti A. Gazz. Chim. Ital. 1963, 93: 90

10 Huisgen R. Möbius L. Szeimies G. Chem. Ber. 1965, 98: 1138

11 Chabala JC. Christensen BG. Ratcliffe RW. Tetrahedron Lett. 1985, 26: 5407

12 Häbich D. Barth W. Heterocycles 1989, 29: 2083

13 Peng W.-m. Zhu S.-Z. J. Fluorine Chem. 2002, 116: 81

14 Pocar D. Stradi R. Rossi LM. J. Chem. Soc., Perkin Trans. 1 1972, 619

15 Pocar D. Stradi R. Rossi LM. J. Chem. Soc., Perkin Trans. 1 1972, 769

16 Nomura Y. Takeuchi Y. Tomoda S. Ito MM. Bull. Chem. Soc. Jpn. 1981, 46: 1800

17 Palacios F. Ochoa de Retana AM. Pagalday J. Sanchez JM. Heterocycles 1995, 40: 543

18 Palacios F. Ochoa de Retana AM. Pagalday J. Sanchez JM. Org. Prep. Proced. Int. 1995, 27: 603

19 Peng W. Zhu S. Synlett 2003, 187

20 Peng W. Zhu S. Tetrahedron 2003, 59: 4395

21 Kadaba PK. J. Org. Chem. 1992, 57: 3075

22 Sasaki T. Eguchi S. Yamaguchi M. Esaki T. J. Org. Chem. 1981, 46: 1800

23 Freeze S. Norris P. Heterocycles 1999, 51: 1807

24 Huisgen R. Möbius L. Mueller G. Stangl H. Szeimies G. Vernon JM. Chem. Ber. 1965, 98: 3992

25 Ondrus TT. Knaus EE. Giam CS. Can. J. Chem. 1979, 57: 2342

26 Warren BK. Knaus EE. J. Med. Chem. 1981, 24: 462

27 Alvarez SG. Alvarez MT. Synthesis 1997, 413

28 Mordini A. Russo F. Valacchi M. Zani L. Degl’Innocenti A. Reginato G. Tetrahedron 2002, 58: 7153

29 Guanti G. Riva R. Tetrahedron: Asymmetry 2001, 12: 1185

30 Lee LV. Mitchell ML. Huang S.-J. Fokin VV. Sharpless KB. Wong C.-H. J. Am. Chem. Soc. 2003, 125: 9588

31 Gibson FS. Park MS. Rapoport H. J. Org. Chem. 1994, 59: 7503

32 Garcia Martinez A. Martinez Alvarez R. Arranz Aguirre J. Subramanian LR. J. Chem. Soc., Perkin Trans. 1 1986, 1595

33 Kraus GA. Krolski ME. Sy J. Org. Synth. 1988, 57: 202

34 See footnote 77 in: Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Eng. 2001, 41: 2004

35 Fleming I. Frontier Orbitals and Organic Reactions Wiley; London: 1976. p.148

36 Kulp SS. J. Chem. Educ. 1988, 65: 742

37 Penning TD. Talley JJ. Bertenshaw SR. Carter JS. Collins PW. Doctor S. Graneto MJ. Lee LF. Malecha JW. Miyashiro JM. Rogers RS. Rogier DJ. Yu SS. Anderson GD. Burton EG. Cogburn JN. Gregory SA. Koboldt CM. Perkins WE. Seibert K. Veenhuizen AW. Zhang YY. Isakson PC. J. Med. Chem. 1997, 40: 1347

38 Demko ZP. Sharpless KB. J. Org. Chem. 2001, 66: 7945

39 L’abbe G. Van Essche G. Bull. Soc. Chim. Belg. 1991, 100: 289