Alkyllithiums as alkylating agents: Regioselective alkylation in the semi-bay region of polycyclic azaarenes

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1863-1866

  Ray, Jayanta K ^a   Roy, Bidhan C ^a   Kar, Gandhi K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008341764     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951848m     Document Type: Article

References (19)

1. Bell, T. W.; Firestone, A. J. Am. Chem. Soc. 1986, 108, 8190.
2. Bell, T. W.; Santora, V. J. Am. Chem. Soc. 1992, 114, 8300 and references cited therein.
3. Bell, T. W.; Firestone, A.; Liu, J.; Ludwig, R.; Rothenburger, S. D. In Inclusion Phenomena, and Molecular Recognition; Atwood, J. L., Ed.; Plenum Press: New York, 1990; pp 49-56.
4. Thummel, R. P.; Jahng, Y. J. Org. Chem. 1985, 50, 2407.
5. Ransoholf, J. E. B.: Stabb, H. A. Tetrahedron Lett. 1985, 26, 6179.
6. Risch, N.; Esser, A. Synthesis 1988, 337.
7. Ashe (III), A. J.; Kampf, J. W.; Savla, P. M. J. Org. Chem. 1990, 55, 5558.
8. 27N: C, 88.77; H, 7.40; N, 3.80. Found: C, 88.61; H, 7.19; N, 3.63.
9. Blout, E. R.; Corley, R. S. J. Am. Chem. Soc. 1947, 69, 763.
10. Selected acridans were aromatized with DDQ in refluxing benzene to give excellent yields of the corresponding azaarenes. (a) Compound 14 gave 7-methyldibenz[c,h]acridine (29): yield 80%; rap 222-223 °C (lit. mp 222-223 °C: Porai-Koshits, A. E.; Ter-Sarkisyan, G. S. Izvest. Akad. Nauk S.S.R., Otdel Khim. Nauk. 1951, 771; Chem. Abstr. 1952, 46, 8116g. The structure of 29 has also been confirmed by X-ray crystallographic analysis.
11. Selected acridans were aromatized with DDQ in refluxing benzene to give excellent yields of the corresponding azaarenes. (a) Compound 14 gave 7-methyldibenz[c,h]acridine (29): yield 80%; rap 222-223 °C (lit. mp 222-223 °C: Porai-Koshits, A. E.; Ter-Sarkisyan, G. S. Izvest. Akad. Nauk S.S.R., Otdel Khim. Nauk. 1951, 771; Chem. Abstr. 1952, 46, 8116g. The structure of 29 has also been confirmed by X-ray crystallographic analysis.
12. 11,13 = 1.2 Hz).
13. 8,10 = 2.2 Hz).
14. (d) The crude product was contaminated with little fully aromatic material. Aromatization afforded 14-n-butyldibenz[a,h]acridine (20).
15. Tobe, Y.; Jimbo, M.; saiki, S.: Kakiuchi, K.; Naemura, J. J. Org. Chem. 1993, 58, 5883.
16. Joub, J. A.; Mill, K. and Smith, G. F. Heterocyclic Chemistry 3rd ed.; Chapman and Hall: London, 1993: pp 80-81 and 123.
17. (a) Buu-Hoi, N. P. J. Chem. Soc. 1950, 1146. However, the structure is not supported by any spectral data. Also, dibenz[a,h]-acridine itself melts at 223-224 °C.
18. (b) The structure of compounds 20 and 27 have also been confirmed by X-ray crystallographic data.
19. Klemm, L. H.; Chiang, E.; O'Bannon, G. W. J. Heterocycl. Chem. 1993, 29, 571 and ref 3 cited therein.