N-(Benzoyloxy)amines: An investigation of their thermal stability, synthesis, and incorporation into novel peptide constructs

Tetrahedron

Volumn 59, Issue 24, 2003, Pages 4315-4325

  Nemchik, Anne ^a   Badescu, Valentina ^a   Phanstiel IV, Otto ^a  

^a UNIVERSITY OF CENTRAL FLORIDA   (United States)

Author keywords

Amine oxidation; Hydroxamic acids; N benzoyloxyamines; Thermal stability; peptides

Indexed keywords

ALANINE DERIVATIVE; ALIPHATIC AMINE; ALPHA AMINO ACID; BUFFER; CARBONIC ACID; PEPTIDE; PEROXIDE;

AQUEOUS SOLUTION; ARTICLE; DECOMPOSITION; ELECTRON; PH; PRIORITY JOURNAL; PYROLYSIS; SYNTHESIS; TEMPERATURE; THERMOSTABILITY;

EID: 0037678803     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00635-5     Document Type: Article

References (20)

1. Bauer L., Exner O. Angew. Chem. Int. Ed. Engl. 13:1974;376-384.
2. Yale H.L. Chem. Rev. 33:1943;209-256.
3. Wang L., Phanstiel O. IV. J. Org. Chem. 65:2000;1442-1447.
4. Milewska M.J., Chimiak A. Synthesis. 1990;233-234.
5. Wang Q.X., King J., Phanstiel O. IV. J. Org. Chem. 62:1997;8104-8108.
6. Wang Q.X., Phanstiel O. IV. J. Org. Chem. 63:1998;1491-1495.
7. Phanstiel O. IV, Wang Q.X., Powell D.H., Ospina M.P., Leeson B.A. J. Org. Chem. 64:1999;803-806.
8. Guo H., Naser S.A., Ghobrial G., Phanstiel O. IV. J. Med. Chem. 45:2002;2056-2063.
9. Bergeron R.J., Phanstiel O. IV. J. Org. Chem. 57:1992;7140-7143.
10. Badescu, V. Synthesis and Thermal Study of a Series of N-Benzoyloxyamines and the Scope and Limitations of an Amine Oxidation Process. Masters Thesis, Department of Chemistry, University of Central Florida, 2000.
11. Badescu, V. Synthesis and Thermal Study of a Series of N-Benzoyloxyamines and the Scope and Limitations of an Amine Oxidation Process. Masters Thesis, Department of Chemistry, University of Central Florida, 2000.
12. Wittman M.D., Halcomb R.L., Danishefsky S.J. J. Org. Chem. 55:1990;1981-1983.
13. Pokonski T., Chimiak A. Tetrahedron Lett. 28:1974;2453-2456.
14. Buckley D., Dunstan S., Henbest H.B. J. Chem. Soc. 1957;4901-4904.
15. Geiger W.B. J. Org. Chem. 23:1958;298-299.
16. Koppel I., Prodel A., Koppel. J. Org. React. (Tartu). 27:(1-2):1990;74-86.
17. McMurry J. Organic Chemistry. 4th ed. 1996;Brooks and Cole, New York. pp 942-943.
18. Carey F.A., Sundberg R.J. Advanced Organic Chemistry, Part A: Structure and Mechanisms. 4th ed. 2000;Kluwer Academic, New York. p 293 and references therein.
19. Carpino L.A., Cohen B.J., Stephens K.E. Jr., Sadat-Aalaee S.Y., Tien J., Langridge D.C. J. Org. Chem. 51:1986;3732-3734.
20. These are known compounds with matching literature NMR data. N-Hexylbenzamide 6a: Katritzky A.R., Drewniak M. J. Chem. Soc., Perkin Trans. 1. 1988;2339-2344. N-Cyclohexyl-benzamide 7a: Kunishima M., Kawachi C., Hioki K., Terao K., Tani S. Tetrahedron. 57:2001;1551-1558. N-Benzylbenzamide 9a: Wan Y., Alterman M., Larhed M., Hallberg A. J. Org. Chem. 67:2002;6232-6235. N-Methylbenzamide 10a: Hajipour A.R., Ghasemi M. Indian J. Chem. 2001;504-507. Tributylamineoxide 18: Ferrer M., Sanchez-Baeza F., Messeguer A. Tetrahedron. 53:1997;15877-15888. N-(2,2,2-Trifluoroethyl)-benzamide 24: Hegarty A.F., Eustace S.J., Tynan N.M., Pham-Tran N.-N., Nguyen M.T. J. Chem. Soc., Perkin Trans. 2. 2001;1239-1246.