Synthesis of new mono- and bi-bridged acridine dimers

Synlett

Volumn , Issue 5, 1999, Pages 641-643

  Issmaili, Saadia ^a   Boyer, Gérard ^a   Galy, Jean Pierre ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Acridines; Bi bridged compounds; DNA intercalands

Indexed keywords

ACRIDINE DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; CYCLIZATION; DEMETHYLATION; INTERCALATION COMPLEX; SYNTHESIS;

EID: 0032960728     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2656     Document Type: Article

References (19)

1. Johnson, D.S.; Boger D.L. in Comprehensive Supramolecular Chemistry; Atwood, J.L., Ed.; Pergamon: Oxford, 1996; vol. 4, ch. 3; Wakelin, L.P.G.; Waring, M.J. in Comprehensive Medicinal Chemistry; Sammes, P.G.; Taylor, J.B., Ed.; Pergamon: Oxford, 1990; vol. 2, ch. 10.1.
2. Johnson, D.S.; Boger D.L. in Comprehensive Supramolecular Chemistry; Atwood, J.L., Ed.; Pergamon: Oxford, 1996; vol. 4, ch. 3; Wakelin, L.P.G.; Waring, M.J. in Comprehensive Medicinal Chemistry; Sammes, P.G.; Taylor, J.B., Ed.; Pergamon: Oxford, 1990; vol. 2, ch. 10.1.
3. Boyer, G.; Galy J.P.; Barbe J. J. Heterocycl. Chem. 1991, 28, 913. Moisan, M.; Galy J.P.; Galy, A.M.; Barbe J. Monatsh. Chem. 1993, 124, 23.
4. Boyer, G.; Galy J.P.; Barbe J. J. Heterocycl. Chem. 1991, 28, 913. Moisan, M.; Galy J.P.; Galy, A.M.; Barbe J. Monatsh. Chem. 1993, 124, 23.
5. Vichet, A.; Patellis A.M.; Galy J.P.; Galy, A.M.; Barbe J.; Elguero J. J. Org. Chem. 1994, 59, 5156. Dhif D.; Galy J.P.; Barbe J. Synth. Commun. 1991, 21, 969.
6. Vichet, A.; Patellis A.M.; Galy J.P.; Galy, A.M.; Barbe J.; Elguero J. J. Org. Chem. 1994, 59, 5156. Dhif D.; Galy J.P.; Barbe J. Synth. Commun. 1991, 21, 969.
7. Corsini, A.; Billo, E.J. J. Inorg. Chem. 1970, 32, 1241.
8. 2-Bromo-3-nitrobenzoic acid was prepared according to the literature: Culhane, P.J. Organic Synthese 1927, 1, 125.
9. 6) δ:117.67 (C-3′), 116.31 (C-6′), 117.82 (C-5), 119.30 (C-1), 120.23 (C-5′), 123.82 (C-4′), 129.41 (C-1′), 130.67 (C-4), 138.58 (C-6), 139.08* (C-3), 139.17* (C-2), 150.10 (C-2′), 168.61 (COOH).
10. See: Brockmann, H.; Muxfeldt, H.; Haese, G. Chem. Ber. 1957, 90, 44.
11. 3), 112.41 (C-6), 116.67 (C-1), 117.16 (C-8), 119.64 (C-3), 120.83 (C-8a), 120.99 (C-7), 121.76(C-9a), 121.78 (C-2), 130.71 (C-4a), 131.32 (C-10a), 133.64 (C-4), 147.80 (C-5), 176.75 (C-9).
12. 2). 78.88 (C), 79.22 (CH), 114.00 (C-6), 114.14 (C-1), 117.42 (C-3), 118.06 (C-8), 120.43 (C-7), 120.99 (C-8a), 121.61 (C-9a), 121.98 (C-2), 129.82 (C-4a), 131.59 (C-10a), 137.35 (C-4), 145.50 (C-5), 176.86 (C-9).
13. 13C NMR δ; 106.09 (C-3), 108.49 (C-6), 113.06 (C-1), 117.57 (C-8), 126.79 (C-7), 127.11 (C-9a), 127.83 (C-2), 134.94 (C-9), 137.83 (C-10a), 138.18 (C-4a), 145.60 (C-4), 153.08 (C-5).
14. 4: C, 72.45; H, 4.91; N, 10.57. Found: C, 72.70; H, 5.11; N, 10.83.
15. Dhif, D.; Galy, J.P.; Barbe, J.; Elguero, J. Heterocycles 1990, 31, 1059.
16. Taylor, E.C.; Hawaks, G.H.; McKillop, A. J. Am. Chem. Soc. 1968, 90, 9, 2421.
17. 6: C, 70.93; H, 4.79; N, 8.95. Found: C, 71.07; H, 4.92; N, 9.21.
18. Matzner, M.; Kurkjy, R.P.; Cotter, R.J. Chem. Rev. 1964, 64, 645.
19. 6: C, 71.47; H, 4.70; N, 8.78. Found: C, 71.72; H, 4.85; N, 9.04.