Conversion of aryl methyl ketimines to 2,5-diarylpyrroles using TiCl4/Et3N

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 4204-4205

  Periasamy, Mariappan ^a   Srinivas, Gadthula ^a   Bharathi, Pandi ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 CHLOROPHENYL) 2,5 DIPHENYLPYRROLE; 1 (4 METHOXYPHENYL) 2,5 DIPHENYLPYRROLE; 1 METHYL 2,5 DIPHENYLPYRROLE; 1 PHENYL 2,5 BIS(2 NAPHTHYL)PYRROLE; 1 PHENYL 2,5 BIS(4 CHLOROPHENYL)PYRROLE; 1 PHENYL 2,5 BIS(4 TOLYL)PYRROLE; 1,2,5 TRIPHENYLPYRROLE; 1,4 DIKETONE; ALIPHATIC AMINE; DICHLOROMETHANE; IMINE; KETONE DERIVATIVE; PYRROLE DERIVATIVE; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; SYNTHESIS;

EID: 0033612387     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982342h     Document Type: Article

References (18)

1. Broadbent, H. S.; Burnharm, W. S.; Olsen, R. K; Sheely, R. M. J. Heterocycl. Chem. 1968, 5, 757.
2. Cooney, J. V.; McEwen, W. E. J. Org. Chem. 1981, 46, 2570.
3. Hantzsch, A. Chem. Ber. 1890, 23, 1474.
4. (a) Bayer, H. O.; Gotthardt, H.; Huisgen, R. Chem. Ber. 1970, 103, 2356.
5. (b) Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefter, F. C. Chem. Ber. 1970, 103, 2611.
6. Berree, F.; Marchand, E.; Morel, G. Tetrahedron Lett. 1992, 33, 6155.
7. Furstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637.
8. Periasamy, M. Unpublished results.
9. (a) Weingarten, H.; Chupp, J. P.; White, W. A. J. Org. Chem. 1967, 32, 3246.
10. (b) Moretti, I.; Torre, G. Synthesis 1979, 141.
11. (c) Corey, E. J.; Gross, A. W. J. Org. Chem. 1985, 50, 5391.
12. (a) Varma, R. S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 2039.
13. (b) Selva, M.; Tundo, P.; Marques, C. A. Synth. Commun. 1996, 25, 369.
14. (c) Taguchi, K.; Westheimer, F. H. J. Org. Chem 1971, 36, 1570.
15. (d) Texier-Boullet, F. Synthesis 1984, 679.
16. Matsumara, Y.; Nishimura, M.; Hiu, H.; Watanabe, M.; Kise, N. J. Org. Chem. 1996, 61, 2809.
17. 3. The solvent was removed, and the ketimine was recrystallized from ethanol. The yields of the ketimines: 1. 91%, 3. 93%, 4. 89%, 5. 90%, 6. 92%, 7. 88%.
18. Zakrzewski, J. J. Organomet. Chem. 1987, 333, 71.