Reagents for Efficient Conversion of Amines to Protected Guanidines

Synthesis

Volumn , Issue 1, 2004, Pages 37-42

  Gers, Tomasz ^a   Kunce, Danuta ^a   Markowski, Paweł ^a   Izdebski, Jan ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

Guanidine; Guanidinylation; Guanylation; Isothiourea; Protecting groups

Indexed keywords

ACETIC ACID; AMINES; UREA;

HYDROGENOLYSIS;

SYNTHESIS (CHEMICAL);

AMINE; BROMINE DERIVATIVE; CARBONYL DERIVATIVE; CHLORINE DERIVATIVE; GUANIDINE DERIVATIVE; METHYL GROUP; N,N' BIS(2 BROMOBENZYLOXYCARBONYL)METHYLISOTHIOUREA; N,N' BIS(2 CHLOROBENZYLOXYCARBONYL)METHYLISOTHIOUREA; N,N' BIS(BENZYLOXYCARBONYL) N'' CYCLOPENTYLGUANIDINE; N,N' BIS(BENZYLOXYCARBONYL) N'' ISOBUTYLGUANIDINE; N,N' BIS(BENZYLOXYCARBONYL) N'' ISOPROPYLGUANIDINE; N,N' BIS(BENZYLOXYCARBONYL) N'' PROPYLGUANIDINE; N,N' BIS(BENZYLOXYCARBONYL) N'' TERT BUTYLGUANIDINE; N,N' BIS(BENZYLOXYCARBONYL)METHYLISOTHIOUREA; N,N' BIS(TERT BUTOXYCARBONYL)METHYLISOTHIOUREA; N,N' BIS(TERT BUTYLOXYCARBONYL) N'' CYCLOPENTYLGUANIDINE; N,N' BIS(TERT BUTYLOXYCARBONYL) N'' ISOBUTYLGUANIDINE; N,N' BIS(TERT BUTYLOXYCARBONYL) N'' ISOPROPYLGUANIDINE; N,N' BIS(TERT BUTYLOXYCARBONYL) N'' PROPYLGUANIDINE; N,N' BIS(TERT BUTYLOXYCARBONYL) N'' TERT BUTYLGUANIDINE; N,N' BIS(TERT BUTYLOXYCARBONYL)METHYLISOTHIOUREA; N,N'' BIS(2 CHLOROBENZYLOXYCARBONYL)METHYLISOTHIOUREA; REAGENT; THIOUREA DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COMPARATIVE STUDY; HYDROGENOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0346688598     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44374     Document Type: Article

References (35)

1. (a) Historical, Biological, Biochemical and Clinical Aspects of the Naturally Occuring Guanidino Compounds; Mori, A.; Cohen, B. D.; Lowenthal, A., Eds.; Plenum: New York, 1983.
2. (b) The Organic Chemistry of Drug Synthesis, Vol. I; Lednicer, D.; Mitscher, L. A., Eds.; Wiley: New York, 1977.
3. (c) The Organic Chemistry of Drug Synthesis, Vol. 11; Lednicer, D.; Mitscher, L. A., Eds.; Wiley: New York, 1980.
4. (d) Berlinck, R. G. S. Fortschr. Chem. Org. Naturst. 1995, 66, 119.
5. (e) Riordan, J. F.; McElvany, K. D.; Borders, C. L. Jr. Science 1977, 195, 884.
6. Xian, M.; Li, X.; Tang, X.; Chen, X.; Zheng, Z.; Galligan, J. J.; Kreulen, D. L.; Wang, P. G. Bioorg. Med. Chem. Lett. 2001, 11, 2377.
7. Baker, T. J.; Luedke, N. W.; Tor, Y.; Goodman, M. J. Org. Chem. 2000, 65, 9054.
8. Hui, Y.; Ptak, R.; Pallansch, M.; Chang, C.-W. W. Tetrahedron Lett. 2002, 43, 9255.
9. Izdebski, J.; Witkowska, E.; Kunce, D.; Orłowska, A.; Baranowska, B.; Radzikowska, M.; Smoluch, M. J. Peptide Sci. 2002, 8, 289.
10. Bajusz, S.; Ronai, A. Z.; Szekely, J. J.; Miglecz, E.; Berzetei, J. FEBS Lett. 1980, 110, 85.
11. Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933.
12. Iwanowicz, E.; Poss, M. A.; Lin, J. Synth. Commun. 1993, 23, 1443.
13. Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677.
14. Robinson, S.; Roskamp, E. J. Tetrahedron 1997, 53, 6697.
15. Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1987, 52, 1700.
16. Guo, Z.-X.; Cammidge, A. N.; Horwell, D. C. Synth. Commun. 2000, 30, 2933.
17. Santagada, V.; Fiorino, F.; Severino, B.; Salvadori, S.; Lazarus, L. H.; Bryant, S. D.; Caliendo, G. Tetrahedron Lett. 2001, 42, 3507.
18. De Mong, D. E.; Williams, R. M. Tetrahedron Lett. 2001, 42, 3529.
19. Verdini, A. S.; Lucietto, P.; Fossati, G.; Giordani, C. Tetrahedron Lett. 1992, 33, 6541.
20. Tian, Z.; Edwards, P.; Roeske, R. W. Int. J. Peptide Protein Res. 1992, 40, 119.
21. Chandrakumar, N. S. Synth. Commun. 1996, 26, 2613.
22. Snider, B. B.; Xie, C. Tetrahedron Lett. 1998, 39, 7021.
23. McAlpine, I. J.; Armstrong, R. W. Tetrahedron Lett. 2000, 41, 1849.
24. Nagasawa, K.; Koshino, H.; Nakata, T. Tetrahedron Lett. 2001, 42, 4155.
25. For the terminology of guanidine formation, see: Jones, J. H. J. Peptide Sci. 2002, 8, 285.
26. Yong, Y. F.; Kowalski, J. A.; Lipton, M. A. J. Org. Chem. 1997, 62, 1540.
27. Yong. Y. F.; Kowalski, J. A.; Lipton, M. A. Tetrahedron Lett. 1999, 40, 53.
28. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34, 3389.
29. Drake, B.; Patek, M.; Lebl, M. Synthesis 1994, 579.
30. Lamin, S. G.; Pedgriff, B. L.; Ratcliffe, A. J. Tetrahedron Lett. 1996, 37, 6815.
31. Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804.
32. Feichtinger, K.; Sings, H. L.; Baker, T. J.; Matthews, K.; Goodman, M. J. Org. Chem. 1998, 63, 8432.
33. (29) Nowak, K.; Kania, L. Rocz. Chem. 1969, 43, 1953; Chem. Abstr. 1970, 72, 67246.
34. Nowak, K.; Kania, L. Rocz. Chem. 1969, 43, 1953; Chem. Abstr. 1970, 72, 67246.
35. Chemistry of Amino Acids, Vol. 3; Greenstein, J. P.; Winitz, M., Eds.; Wiley: New York, 1961, Chap. 22, 1841.