Base-mediated reactions of ortho- and para-perfluoroalkylanilines

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4655-4658

  Strekowski, Lucjan ^a   Lin, Shou Yuan ^a   Lee, Hyeran ^a   Mason, J Christian ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030199704     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00913-6     Document Type: Article

References (14)

1. 1. For reviews, see: a) Strekowski, L.; Kiselyov, A.S. Trends Heterocycl. Chem. 1993, 3, 73.
2. b) Kiselyov, A.S.; Strekowski, L. Org. Prep. Proc. Int. 1996 (in press.)
3. 2. Strekowski, L.; Kiselyov, A.S.; Hojjat, M. J. Org. Chem. 1994, 59, 5886.
4. 3. a) Kiselyov, A.S. Tetrahedron Lett. 1995, 36, 1383.
5. b) Strekowski, L.; Patterson, S.E.; Janda, L.; Wydra, R.L.; Harden, D.B.; Lipowska, M.; Cegla, M.T. J. Org. Chem. 1992, 57, 196.
6. 4. a) Yoshino, N.; Kitamura, M.; Seto, T.; Shibata, Y.; Abe, M.; Ogino, K. Bull. Chem. Soc. Jpn. 1992, 65, 2141.
7. b) Chen, Q.-Y.; Chen, Y.-X.; Huang, W.-Y. Acta Chim. Sinica 1984, 42, 906.
8. 4), concentration, and silica gel chromatography with pentanes/ether (5:1) as an eluent.
9. 1H-NMR spectrum of compound 10 (mp 181-182 °C) was virtually identical with the spectrum of 9-phenylacridine obtained by an independent method: Lehmstedt, K.; Dostal, F. Chem. Ber. 1939, 72, 804 (reported mp 183 °C).
10. 1 mechanism of cyclization of 8, in which the amide anion would undergo intramolecular addition to position ortho of the phenyl group and fiuoride ion would be eliminated, is less likely because amide bases exhibit relatively low nucleophilicity.
11. 8. A solution of EtONa (prepared from 0.23 g of sodium, 10 mmol) and 2a or 2b (0.62 g, 2 mmol) in EtOH (10 mL) was heated under reflux and under a nitrogen atmosphere for 4 h. Standard workup was followed by Kugelrohr distillation (170 °C/10 mm Hg).
12. 4 (1.0 g, 26 mmol) in ether (25 mL) was treated dropwise with a solution of 2a or 2b (0.4 g, 1.3 mmol) in ether (2 mL) under a nitrogen atmosphere and the resultant mixture was heated under reflux for 18 h. Standard workup was followed by chromatography on silica gel with pentanes/ether (5:1) as an eluent.
13. 10. Bernardin, J.; Pechmeze, J. Ger. Offen. DE 2606982, Aug. 26, 1976 (Chem. Abstr. 85:192333).
14. 10. Bernardin, J.; Pechmeze, J. Ger. Offen. DE 2606982, Aug. 26, 1976 (Chem. Abstr. 85:192333).