Conversion of N-Acyl Amino Acids into Imides via Oxidative Decarboxylation Induced by Ag⁺/Cu²⁺/S₂O₈ ^2- in Water

Abstract

N-Acyl amino acids can be converted by oxidative decarboxylation induced by Ag⁺/Cu²⁺/S₂O₈ ^2- at room temperature in water into imides in 24-89% yields. Both N-benzoylvaline and N-benzoylleucine gave N-formylbenzamide, which possibly results from oxidative cleavage of an enamide intermediate.

Key words

oxidative decarboxylation - silver - copper - imide - amino acid

References

• 1 Boto A. Hernandez R. de Leon Y. Suarez E. J. Org. Chem.  2001,  66:  7796 ; and references therein
• 2 Majer F. Schmid DG. Altena K. Bierbaum G. Kupke T. J. Bacteriol.  2002,  184:  1234 
• 3a Gledhill AP. McCall CJ. Threadgill MD. J. Org. Chem.  1986,  51:  3196 
• 3b Ochiai M. Inenaga M. Nagao Y. Moriarty RM. Vaid RK. Duncan MP. Tetrahedron Lett.  1988,  29:  6917 
• 4a Suda K. Hino F. Yijima C. Chem. Pharm. Bull.  1985,  33:  882 
• 4b Lucente G. Pinnen F. Sanotti G. Tetrahedron Lett.  1978,  19:  3155 
• 5a Itoh A. Kodama T. Inagaki S. Masaki Y. Chem. Lett.  2000,  542 
• 5b Itoh A. Kodama T. Masaki Y. Inagaki S. Chem. Pharm. Bull.  2006,  54:  1571 
• 6a Minisci F. Vismara E. Fontana F. Heterocycles  1989,  28:  489 
• 6b Tada M. Furuse R. Kashima H. Heterocycles  1992,  34:  357 
• 6c Cowden CJ. Org. Lett.  2003,  5:  4497 
• 7a Huang W. Zhang L. J. Chem. Res., Synop.  2006,  738 
• 7b

  We thank a reviewer for suggesting this explanation.

• 8 Grigg R. Gunaratne HQN. Sridharan V. Chem. Commun.  1985,  1183 
• 9 Needles HL. Ivanetich K. Chem. Ind. (London)  1967,  581 
• 10a Holland HL. Andreana PR. Salehzadeh-Asl R. van Vilet A. Ihasz NJ. Brown FM. Monatsh. Chem.  2000,  131:  667 
• 10b Leone-Bay A. Santiago N. Achan D. Chaudhary K. DeMorin F. Falzarano L. Haas S. Kalbag S. Kaplan D. Leipold H. Lercara C. O’Toole D. Rivera T. Rosado C. Sarubbi D. Vuocolo E. Wang N. Milstein S. Baughman RA. J. Med. Chem.  1995,  38:  4263 
• 10c Youshko MI. van Langen LM. Sheldon RA. Svedas VK. Tetrahedron: Asymmetry  2004,  15:  1933 
• 10d Barton DHR. Ferreira JA. Tetrahedron  1996,  52:  9367 
• 11a Moffatt JG. Lerch U. J. Org. Chem.  1971,  36:  3391 
• 11b Morris JM. Dunmire RB. Newkome GR. Koenig PE. J. Org. Chem.  1972,  37:  1244 
• 11c Gramain JC. Simonet N. Vermeersch G. Febvay-Garot N. Caplain S. Lablache-Combier A. Tetrahedron  1982,  38:  539 
• 11d Giovannini A. Savoia D. Umani-Ronchi A. J. Org. Chem.  1989,  54:  228 
• 12a Etter MC. Reutzel SM. J. Am. Chem. Soc.  1991,  113:  2586 
• 12b Sasaki H. Mori Y. Nakamura J. Shibasaki J.
  J. Med. Chem.  1991,  34:  628