Preparation of amidines by amidoxime reduction with potassium formate

Synlett

Volumn , Issue 8, 2007, Pages 1257-1258

  Nadrah, Kristina ^a   Dolenc, Marija Sollner ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Amidines; Green chemistry; Palladium; Reductions

Indexed keywords

AMIDINE; FORMIC ACID; OXIME DERIVATIVE; POTASSIUM;

ACYLATION; ARTICLE; CHEMICAL REACTION; REDUCTION; SYNTHESIS;

EID: 34249794573     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977444     Document Type: Article

References (29)

1. (a) Rewinkel, J. B. M.; Adang, A. E. P. Curr. Pharm. Des. 1999, 5, 1043.
2. (b) Scarborough, R. M.; Gretler, D. D. J. Med. Chem. 2000, 43, 3453.
3. Sielecki, T. M.; Liu, J.; Mousa, S. A.; Racanelli, A. L.; Hausner, E. A.; Wexler, R. R.; Olson, R. E. Bioorg. Med. Chem. Lett. 2001, 11, 2201.
4. Collins, J. L.; Shearer, B. G.; Oplinger, J. A.; Lee, S.; Garvey, E. P.; Salter, M.; Dufry, C.; Burnette, T. C.; Furtine, E. S. J. Med. Chem. 1998, 41, 2858.
5. Nakamura, H.; Sasaki, Y.; Uno, M.; Yoshikawa, T.; Asano, T.; Ban, H. S.; Fukazawa, H.; Shibuya, M.; Uehara, Y. Bioorg. Med. Chem. Lett. 2006, 16, 5127.
6. Stephens, C. E.; Tanious, E.; Kim, S.; Wilson, D. W.; Schell, W. A.; Perfect, J. R.; Franzblau, S. G.; Boykin, D. W. J. Med. Chem. 2001, 44, 1741.
7. Roger, R.; Nielson, D. G. Chem. Rev. 1961, 61, 179.
8. (a) Bredereck, H.; Gompper, R.; Seiz, H. Chem. Ber. 1957, 90, 1837.
9. (b) Lage, U. W.; Schäfer, B.; Baucke, D.; Buschmann, E.; Mack, H. Tetrahedron Lett. 1999, 40, 7067.
10. Garigipati, R. S. Tetrahedron Lett. 1990, 31, 1969.
11. (a) Eloy, F. Fortschr. Chem. Forsch. 1965, 4, 807.
12. (b) Moormann, A. E.; Wang, J. L.; Palmquist, K. E.; Promo, M. A.; Snyder, J. S.; Scholten, J. A.; Massa, M. A.; Sikorski, J. A.; Webber, R. K. Tetrahedron 2004, 60, 10907.
13. (c) Sendzik, M.; Hui, H. C. Tetrahedron Lett. 2003, 44, 8697.
14. (a) Eloy, F.; Lenaers, R. Chem. Rev. 1962, 62, 155.
15. (b) Judkins, B. D.; Allen, D. G.; Cook, T. A.; Evans, B.; Sardharwala, T. E. Synth. Commun. 1996, 26, 4351.
16. (c) Dener, J. M.; Wang, V. R.; Rice, K. D.; Gangloff, A. R.; Kuo, E. Y.-L.; Newcomb, W. S.; Putnam, D.; Wong, M. Bioorg. Med. Chem. Lett. 2001, 11, 2325.
17. (d) Lepore, S. D.; Schacht, A. L.; Wiley, M. R. Tetrahedron Lett. 2002, 43, 8777.
18. Judkins, B. D.; Allen, D. G.; Cook, T. A.; Evans, B.; Sardharwala, T. E. Synth. Commun. 1996, 26, 4351.
19. Zierke, T.; Mack, H. Int. Patent, WO 0061574, 2000; Chem. Abstr. 2000, 133, 282087.
20. Anbazhagan, M.; Boykin, D. W.; Stephens, C. E. Synthesis 2003, 2467.
21. Wiener, H.; Blum, J.; Sasson, Y. J. Org. Chem. 1991, 56, 4481.
22. (a) Wiener, H.; Blum, J.; Sasson, Y. J. Org. Chem. 1991, 56, 6145.
23. (b) Anwer, M. K.; Sherman, D. B.; Roney, J. G.; Spatola, A. F. J. Org. Chem. 1989, 54, 1284.
24. Anwer, M. K.; Spatola, A. F. Synthesis 1980, 929.
25. (a) Anwer, M. K.; Spatola, A. F. Tetrahedron Lett. 1981, 22, 4369.
26. (b) Anwer, M. K.; Spatola, A. F. J. Org. Chem. 1983, 48, 3503.
27. Typical Procedure for Reduction of Amidoxime: The parent amidoxime (1 mmol) was dissolved in a mixture of glacial AcOH (1 mL) and potassium formate solution in MeOH (10 mmol), followed by the addition of 10% Pd/C. The mixture was stirred at r.t. until the reaction was complete based on TLC. Isolation and purification were performed as described in ref. 19 to yield pure amidine hydrochloride.
28. 2O (1.1 mmol) was added at r.t. After 5 min, potassium formate solution in MeOH was added, followed by 10% Pd/C. The mixture was stirred at r.t. until reaction was complete based on TLC. The solids were filtered, washed with MeOH or EtOH, and the filtrate was evaporated. The residue was dissolved in anhyd EtOH and 5 M HCl in anhyd EtOH (12 equiv) was then added. The solids were filtered, washed with anhyd EtOH and the filtrate was evaporated to yield pure amidine hydrochloride.
29. 2: 178.0742; found: 178.0750.