N,N′-Di-tert-butoxycarbonyl-1H-benzotriazole-1 -carboxamidine derivatives are highly reactive guanidinylating reagents

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3859-3861

  Musiol, Hans JUrgen ^a   Moroder, Luis ^a  

^a MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001006451     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010191q     Document Type: Article

References (28)

1. (a) Berlinck, R. G. S. Fortschr. Chem. Org. Nat. 1995, 66, 119-295.
2. (b) Berlinck, R. G. D. Nat. Prod. Rep. 1999, 16, 339-365.
3. (c) Greenhill, J. L.; Lue, P. In Amidines and Guanidines in Medicinal Chemistry; Elli, G. P., Luscombe, D. K., Eds.; Progress in Medicinal Chemistry; Elsevier Science: Amsterdam, 1993; Vol. 30. pp 203-326.
4. Yamamoto, Y.; Kojima, S. In The Chemistry of Amidines and Imidates; Patai, S., Rappoport, Z., Eds.: Wiley: New York, 1991; Vol. 2, pp 486-526.
5. (a) Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933-36.
6. (b) Verdini, A. S.; Lucietto, P.; Fossati, G.; Giordani, C. Tetrahedron Lett. 1992, 33, 6541-6542.
7. (c) Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677-7680.
8. (d) Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34, 3389-3392.
9. (e) Wu, Y.; Matsueda, G. R.; Bernatowicz, M. S. Synth. Commun. 1993, 23, 3055-3060.
10. (f) Drake, B.; Patek, M.; Lebl, M. Synthesis 1994, 579-582.
11. (g) Su, W. Synth. Commun. 1996, 26, 407-413.
12. (h) Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1987, 52, 1700-1703.
13. (i) Tian, Z.; Edwards, P.; Roeske, R. W. Int. J. Pept. Protein Res. 1992, 40, 119-126.
14. (j) Lal, B.; Gangopadhyay, A. K. Tetrahedron Lett. 1996, 37, 2483-2486.
15. (k) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804-3805.
16. (1) Feichtinger, K.; Sings, H. L.; Baker, T. J.; Matthews, K.; Goodman, M. J. Org. Chem. 1998, 63, 8432-8439.
17. (m) Zapf, C. W.; Creighton, C. J.; Tomioka, M.; Goodman, M. Org. Lett. 2001, 3, 1133-1136.
18. (n) Guo, Z.-X.; Cammidge, A. N.; Horwell, D. C. Synth. Commun. 2000, 30, 2933-2943.
19. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497-2502.
20. (a) Katritzky, A. R.; Parris, R. L.; Allin, S. M. Synth. Commun. 1995, 25, 1173-1186.
21. (b) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080-8082.
22. 3).
23. Zincke, Th.; Stoffel, F.; Petermann, E. Ann. Chem. 1900, 311, 277-329.
24. 31
25. 10b
26. (a) Yong, Y. F.; Kowalski, J. A.; Lipton, M. A. J. Org. Chem. 1997, 62, 1540-1542.
27. (b) Yong, Y. F.; Kowalski, J. A.; Thoen, J. C.; Lipton, M. A. Tetrahedron Lett. 1999, 40, 53-56.
28. 2/TFE/AcOH (8:1:1) at 20 °C for 1 h.