A novel photo-assisted annulation reaction for the synthesis of 6,7-dichloroimidazo[4,5-b]quinolin-2-one

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 1937-1940

  Zhu, Zhijian ^a   Lippa, Blaise S ^a   Townsend, Leroy B ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

imidazo 4,5 b quinolin 2 one; photo assisted annulation

Indexed keywords

6,7 DICHLOROIMIDAZO[4,5 B]QUINOLIN 2 ONE; IMIDAZOLE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029940632     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00308-5     Document Type: Article

References (17)

1. a). Townsend, L. B.; Devivar, R. V.; Turk, S. R.; Nassiri, M. R.; Drach, J. C. J. Med. Chem. 1995, 38, 4098-4105.
2. b). Townsend, L. B.; Drach, J. C.; et al. presented at the Fifth Internat. Conf. Antiviral Res., Vancouver, BC, 1992; Abstracts 12, 105, 107, 108, 110.
3. a). Leonard, N.J.; Hiremath, S.P. Tetrahedron 1986, 42, 1917-1961.
4. b). Leonard, N.J. Acc. Chem. Res. 1982, 15, 128-135.
5. a). Meanwell, N. A.; Roth, H. R.; Smith, E. C. R.; Wedding, D. L.; Wright, J. J. K.; Fleming, J. S.; Gillespie, E. J. Med. Chem. 1991, 34, 2906-2916.
6. b). Meanwell, N. A.; Roth, H. R.; Smith, E. C. R.; Wedding, D. L.; Wright, J. J. K. J. Org. Chem. 1991, 56, 6897-6904.
7. a). Reid, W.; Grabosch, J. Chem. Ber. 1956, 89, 2684-2687.
8. b). Connors, T. A.; Ross, W. C. J.; Wilson, J. G. J. Chem. Soc. 1960, 2994-3007.
9. c). Kozuk., J.; Musail, L. Bull. Int. Acad. Pol. A 1930, 432-438 (Chem. Abstr. 1931, 25, 5400).
10. c). Kozuk., J.; Musail, L. Bull. Int. Acad. Pol. A 1930, 432-438 (Chem. Abstr. 1931, 25, 5400).
11. a). Horner, J. K.; Henry, D. W. J. Med. Chem. 1968, 11, 946-949.
12. b). We synthesized 4,5-dichloro-2-nitrobenzaldehyde from 4,5-dichloro-2-nitroaniline in an overall 50 % yield (4 steps).
13. 4(302): C, 39.74; H, 1.66; N, 13.91. Found: C, 39.97; H, 1.48; N, 13.70.
14. a). Ninomiya, I.; Noito, T. Photochemical Synthesis, Cambridge University Press, 1987, 2nd Ed., Chapter 4.
15. b). Hammond, G. S.; Saltiel, J.; Lamola, A. A.; Turro, N. J.; Bradshaw, J. S.; Cowan, D. O.; Counsell, R. C.; Vogt, V.; Dalton, C. J. Am. Chem. Soc. 1964, 86, 3197-3217.
16. 2).
17. 2(254): C, 47.24; H, 1.97; N, 16.53; Found: C, 47.00; H, 2.05; N, 16.39.