Unexpected behavior of imines derived from trifluoromethylaryl ketones under basic conditions: Convenient synthesis of 2-arylbenzimidazoles and 2-arylbenzoxazoles.

Tetrahedron Letters

Volumn 40, Issue 22, 1999, Pages 4119-4122

  Kiselyov, Alexander S ^a  

^a AMGEN INC   (United States)

Author keywords

Benzimidazoles; Benzoxazoles; Cyclization; Imines

Indexed keywords

1,2 PHENYLENEDIAMINE; 2 AMINOPHENOL; BENZIMIDAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; IMINE; KETONE; MORPHOLINE; PIPERIDINE; PRASEODYMIUM COMPLEX;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS;

EID: 0033612167     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00632-2     Document Type: Article

References (22)

1. a) Kiselyov, A.S.; Strekowski, L. Org.Prep.Proc.Int. 1996, 28, 289; and references cited therein;
2. b) Strekowski, L.; Kiselyov, A.S. Trends Heterocycl.Chem. 1993, 73.
3. Hojjat, M.; Kiselyov, A.S.; Strekowski, L. Synth.Commun. 1994, 24, 267.
4. Kiselyov, A.S.; Hojjat, M.; Van Aken, K.; Strekowski, L. Heterocycles 1994, 37, 775.
5. Wydra, R.; Patterson, S.E.; Strekowski, L. J. Heterocycl.Chem. 1990, 27, 803.
6. Strekowski, L.; Lin, S.-Y.; Nguyen, J.; Redmore, N.; Mason, J.C.; Kiselyov, A.S. Heterocycl. Commun. 1995, 1, 331.
7. Strekowski, L.; Wydra, R.; Kiselyov, A.S.; Baird, J.H. Synth.Commun. 1994, 24, 257.
8. a) Strekowski, L.; Patterson, S.E.; Janda, L.; Wydra, R.; Harden, D.B.; Lipowska, M.; Cegla, M. J.Org.Chem. 1992, 57, 196;
9. b) Strekowski, L.; Wydra, R.; Cegla, M.T.; Czamy, A.; Harden, D.B.; Patterson, S.E.; Battiste, M.A.; Coxon, J.M. J.Org.Chem. 1990, 55, 4777;
10. c) Janda, L.; Nguyen, J.; Patterson, S.E.; Strekowski, L. J.Heterocycl.Chem. 1992, 29, 1753.
11. Strekowski, L.; Wydra, R.; Harden, D.B.; Honkan, V.A. Heterocycles 1990, 31, 1565.
12. Strekowski, L.; Kiselyov, A.S.; Hojjat, M. J.Org.Chem.1994, 59, 5886.
13. Kiselyov, A.S.; Strekowski, L. Tetrahedron Lett. 1994, 35, 7597.
14. Kiselyov, A.S. Tetrahedron Lett. 1995, 36, 1383.
15. Prepared according to the procedure previously reported: Kiselyov, A.S.; Harvey, R.G. Tetrahedron Lett. 1995, 36, 4005.
16. Formation of bis-imines from the diamines 1a, 1c, and 1d have not been detected.
17. The authenticity of the isolated benzimidazoles has been confirmed by comparison of their melting points (uncorrected), 1H NMR, and mass-spectra with the data reported.
18. Major isolated product. Reaction resulted in a complex mixture of compounds.
19. 3 group with the nucleophile (Li(piperidide) is shown) followed by the intramolecular attack of the anilinic nitrogen on the carbon of the imine, and elimination of the secondary amine: (formula presented) For examples of nucleophilic displacement of a perfluoroalkyl substituent see : a) Chambers, R.D.; Sargent, C.R. In: Advances in Heterocyclic Chemistry, Ed. by Katritzky, A.R. and Boulton, A.J.; Academic Press: New York-London-Toronto-Sydney-San Francisco, 1981, Vol. 28, 1; b) Bergman, J.; Bergman, S. J.Org.Chem. 1985, 50, 1246 ; c) Kobayashi, Y.; Kumadaki, I. Chem.Rev. 1978, 11, 197.
20. 3 group with the nucleophile (Li(piperidide) is shown) followed by the intramolecular attack of the anilinic nitrogen on the carbon of the imine, and elimination of the secondary amine: (formula presented) For examples of nucleophilic displacement of a perfluoroalkyl substituent see : a) Chambers, R.D.; Sargent, C.R. In: Advances in Heterocyclic Chemistry, Ed. by Katritzky, A.R. and Boulton, A.J.; Academic Press: New York-London-Toronto-Sydney-San Francisco, 1981, Vol. 28, 1; b) Bergman, J.; Bergman, S. J.Org.Chem. 1985, 50, 1246 ; c) Kobayashi, Y.; Kumadaki, I. Chem.Rev. 1978, 11, 197.
21. 3 group with the nucleophile (Li(piperidide) is shown) followed by the intramolecular attack of the anilinic nitrogen on the carbon of the imine, and elimination of the secondary amine: (formula presented) For examples of nucleophilic displacement of a perfluoroalkyl substituent see : a) Chambers, R.D.; Sargent, C.R. In: Advances in Heterocyclic Chemistry, Ed. by Katritzky, A.R. and Boulton, A.J.; Academic Press: New York-London-Toronto-Sydney-San Francisco, 1981, Vol. 28, 1; b) Bergman, J.; Bergman, S. J.Org.Chem. 1985, 50, 1246 ; c) Kobayashi, Y.; Kumadaki, I. Chem.Rev. 1978, 11, 197.
22. A similar behavior of the imines towards n-BuLi, and Grignard reagents was documented, see for example: Strekowski, L.; Cegla, M.T.; Harden, D.B.; Mokrosz, J.L.; Mokrosz, M.J. Tetrahedron Lett. 1988, 29, 4265.