Unexpected formation of N,N-disubstituted formamidines from aromatic amines, formamides and trifluoroacetic anhydride

Tetrahedron

Volumn 62, Issue 24, 2006, Pages 5617-5625

  Mekhalfia, Abdelaziz ^a   Mutter, Roger ^a   Heal, William ^a   Chen, Beining ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

Formamide; Formamidine; Trifluoroacetamide; Trifluoroacetic anhydride

Indexed keywords

AROMATIC AMINE; FORMAMIDE; FORMAMIDINE; SOLVENT; TRIFLUOROACETIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION KINETICS; MOLECULAR MECHANICS; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; VILSMEIER HAACK REACTION;

EID: 33646342736     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.099     Document Type: Article

References (48)

1. Beeman R.W., and Matsumura F. Nature 242 (1973) 273
2. Zieglerskylakakis K., Nill S., Pan J.F., and Andrae U. Environ. Mol. Mutagen. 31 (1998) 362
3. Kerr S.G., and Kalman T.I. J. Pharm. Sci. 83 (1994) 582
4. Cooper R.L., Barrett M.A., Goldman J.M., Rehnberg G.R., Mcelroy W.K., and Stoker T.E. Fundam. Appl. Toxicol. 22 (1994) 474
5. Donetti A., Cereda E., Bellora E., Gallazzi A., Bazzano C., Vanoni P.C., Del Soldato P., Micheletti R., Pagani F., and Giachetti A. J. Med. Chem. 27 (1984) 380
6. Scott M.K., Jacoby H.J., Mills J.E., Bonfilio A.C., and Rasmussen C.R. J. Med. Chem. 26 (1983) 535
7. Leauza W.J., Wildouger K.J., Miller T.W., and Christensen B.G. J. Med. Chem. 22 (1979) 435
8. Aziz S.A., and Knowles C.O. Nature 242 (1973) 417
9. Komber H., Limbach H.H., Bohme F., and Kunner C. J. Am. Chem. Soc. 124 (2002) 11955
10. Tenkovvtsev A.V., Yakimanski A.V., Dudkina M.M., Lukoshkin V.V., Komber H., Haussler L., and Bohme F. Macromolecules 34 (2001) 7100
11. Bohme F., Kunert C., Klinger C., and Komber H. Macromol. Symp. 128 (1998) 183
12. Bohme F., Klinger C., Komber H., Haussler L., and Jehnichen D. J. Polym. Sci., Part A: Polym. Chem. 36 (1998) 929
13. Parthasarathy V.R. Tappi J. 80 (1997) 159
14. Marchildon L., Daneault C., Leduc C., and Sain M.M. Cellul. Chem. Technol. 30 (1996) 473
15. Daneault C., and Leduc C. Tappi J. 78 (1995) 153
16. Virgilio, J. A.; Emanuel, W.; Fairfield, H.; Cohen, I. D.; Brooklyn, N. United States Patent. 1993, US 005, 243, 055 A.
17. Ren T., DeSilva V., Zou G., Lin C., Danels L.M., Campana C.F., and Alvarez J.C. Inorg. Chem. Commun. 2 (1999) 301
18. Mitzi D.B., and Liang K. J. Solid State Chem. 134 (1997) 376
19. Arnold D.I., Cotton F.A., Matonic J.H., and Murillo C.A. Polyhedron 16 (1997) 1837
20. Singhal A., and Jain V.K. Can. J. Chem. 74 (1996) 2018
21. Nicolo F., Bruno G., Loschiavo S., Sinicropi M.S., and Piraino P. Inorg. Chim. Acta 223 (1994) 145
22. Rudyk H., Knaggs M.H., Vasiljevic S., Hope J., Birkett C., and Gilbert I.H. Eur. J. Med. Chem. 38 (2003) 567
23. Pocha F. Tetrahedron 16 (1986) 4461
24. Furth P.S., Reitman M.S., Gentles R., and Cook A.F. Tetrahedron Lett. 38 (1997) 6643
25. Furth P.S., Reitman M.S., and Cook A.F. Tetrahedron Lett. 38 (1997) 5403
26. Meyers A.I., and Hutchings R. Heterocycles 42 (1996) 475
27. Meyers A.I., Gonzalez M.A., Struzka V., Akahane A., Guiles J., and Warmus J.S. Tetrahedron Lett. 32 (1991) 5501
28. Meyers A.I., and Hutchings R.H. Tetrahedron 49 (1993) 1807
29. Meyers A.I., and Elworthy T.R. J. Org. Chem. 57 (1992) 4732
30. Meyers A.I. Tetrahedron 48 (1992) 2589
31. Partridge M.W., and Smith A. J. Chem. Soc., Perkin Trans. 1 (1973) 453
32. Matulenko M.A., and Meyers A.I. J. Org. Chem. 61 (1996) 573
33. Bottomley W., and Boyd G.V. J. Chem. Soc., Chem. Commun. (1980) 790
34. Besan J., Kulcsar L., and Kovacs M. Synthesis (1980) 883
35. Pedersen E.B. Synthesis (1979) 546
36. Hill A.J., and Johnson J.V. J. Am. Chem. Soc. 76 (1954) 920
37. Mandel G., and Hill A.J. J. Am. Chem. Soc. 76 (1954) 3978
38. Delarue S., and Sergheraert C. Tetrahedron Lett. 40 (1999) 5487
39. Boulton L.T., Fox M.E., Hodgson P.B., and Lennon I.C. Tetrahedron Lett. 46 (2005) 983
40. Bredereck H., Gomper R., Klen H., and Kempfer M. Chem. Ber. 92 (1959) 837
41. Seela F., and Shaikh K.I. Tetrahedron 61 (2005) 2675
42. Saito I., Miyauchi Y., Saito Y., and Fujimoto K. Tetrahedron Lett. 46 (2005) 97
43. Schroeder M.C., Hamby J.M., Connolly C.J.C., Grohar P.J., Winters R.T., Barvian M.R., Moore C.W., Boushelle S.L., Crean S.M., Kraker A.J., Driscoll D.L., Vincent P.W., Elliott W.L., Lu G.H., Batley B.L., Dahring T.K., Major T.C., Panek R.L., Doherty A.M., and Showalter H.D.H. J. Med. Chem. 44 (2001) 1915
44. Cai L., Han Y., Ren S., and Huang L. Tetrahedron 56 (2000) 8253
45. Reddy T.R.K., Mutter R., Heal W., Guo K., Gillet V., Pratt S., and Chen B. J. Med. Chem. 49 (2006) 607
46. Svirskaya P.I., Leoznoff C.C., and Steinman M. J. Org. Chem. 52 (1987) 1362
47. Stauffer C.E. J. Am. Chem. Soc. 94 (1972) 7887
48. Salazar J., López S.E., and Rebollo O. J. Fluorine Chem. 124 (2003) 111