Efficient synthesis of 1,4,5,12-tetraazatriphenylene and derivatives

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7741-7744

  Abeywickrama, Chandima ^a   Baker, Arthur David ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION; DERIVATIVES; KETONES; SYNTHESIS (CHEMICAL);

1,4,5,12-TETRAAZATRIPHENYLENE; DIAMINOMALEONITRILE; DICARBONITRILE; GLYOXAL;

AROMATIC COMPOUNDS;

1,2 DICARBONYL DERIVATIVE; 1,4,5,12 TETRAAZATRIPHENYLENE; 1,4,5,12 TETRAAZATRIPHENYLENE 2,3 DICARBONITRILE; 1,4,5,12 TETRAAZATRIPHENYLENE DERIVATIVE; 5,6 DIAMINO 4,7 PHENANTHROLINE; DIAMINOMALEONITRILE; GLYOXAL; HETEROCYCLIC COMPOUND; NITRILE; PHANQUINONE; PHENANTHROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; POLYMERIZATION; REACTION ANALYSIS; REPRODUCIBILITY; SYNTHESIS; TECHNIQUE;

EID: 6344278339     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0495283     Document Type: Article

References (30)

1. (a) Eilatin is a heptacyclic alkaloid from the purple red sea tunicate Eudistoma sp. Its metal complexes intercalate DNA.
2. (b) Kuanoniamine A has been isolated from the purple marine Cystodytes sp. It inhibits HCT replication: Ding, Q.; Chichak, K.; Lown, J. W. Curr. Med. Chem. 1999, 6, 1.
3. Ascididemin isolated from Mediterranean ascidian Cystodytes dellechiajei is cytotoxic toward human leukemic cells and intercalates DNA: Bonnard, I.; Bontemps, N.; Lahmy, S.; Banaigs, B.; Combaut, G.; Francisco, C.; Colson, P.; Houssier, C.; Waring, M. J.; Bailly, C. Anti-Cancer Drug Des. 1995, 10, 333.
4. 2-Bromoleptoclinidinone isolated from an ascidian is an anti-leukemic alkaloid and its metal complexes intercalate DNA: Goulle, V.; Lehn, J.; Schoentjes, B.; Schmitz, F.; Goulle, V.; Lehn, J. M.; Schoentjes, B.; Schmitz, F. J. Helv. Chim. Acta 1991, 74, 1471.
5. The structures and uses of several such synthetic materials are available in the Supporting Information.
6. Fuchs, Y.; Lofters, S.; Dieter, T.; Shi, W.; Morgan, R.; Strekas, T. C.; Gafney, H. D.; Baker, A. D. J. Am. Chem. Soc. 1987, 109, 2691.
7. Cola, L. D.; Barigelletti, F. Gazz. Chim. Ital. 1988, 118, 417.
8. Grove, H.; Sletten, J. J. Chem. Crystallogr. 2000, 30, 123.
9. Grove, H.; Sletten, J.; Julve, M.; Lloret, F.; Cano, Juan. J. Chem. Soc., Dalton. 2001, 259.
10. Erkkila, K. E.; Odom, D. T.; Barton, J. K. Chem. Rev. 1999, 99, 2777.
11. Baker, A. D.; Morgan, R. J.; Strekas, T. C. J. Chem. Soc., Chem. Commun. 1992, 1099.
12. Baker, A. D.; Morgan, R. J.; Strekas, T. C. J. Am. Chem. Soc. 1991, 113, 1411.
13. Yoo, H.; Suh, M.; Shin, K. J.; Park, S. Bull. Kor. Chem. Soc. 1997, 18, 484.
14. Wang, L.; Le, X. Y.; Ji, L. N. Polym. Adv. Technol. 1996, 7, 723.
15. Pfeiffer, F. R.; Case, F. H. J. Org. Chem. 1966, 31, 3384.
16. Case, F. H. J. Heterocycl. Chem. 1987, 157.
17. Bonhôte, P.; Wrighton, M. S. Synlett 1997, 897.
18. Holzmann, G.; Rothkopf, H. W.; Muller, R.; Wohrle, D. Org. Mass Spectrom. 1973, 10, 97.
19. Rothkopf, H. W.; Wohrle, D.; Muller, R.; Kossmehl, G. Chem. Ber, 1975, 108, 875.
20. Linsker, F.; Evans, R. L. J. Am. Chem. Soc. 1946, 68, 403.
21. Yamada, M.; Tanaka, Y.; Yoshimoto, Y.; Kuroda, S.; Shimao, I. Bull. Chem. Soc. Jpn. 1992, 65, 1006.
22. 6 coefficients are actually lower than on any other carbon atoms in the HOMO of 4,7-isomer.
23. Imor, S.; Morgan, R. J.; Wang, S.; Morgan, O.; Baker, A. D. Synth. Commun. 1998, 26, 2197.
24. Meier, R.; Schuler, W.; Krueger, R. Arch. Exp. Path. U. Pharmakol. 1955, 224, 206.
25. Skujins, S.; Webb, G. A. Tetrahedron 1989, 25, 3935.
26. Amer, A. M.; El-Bahnasawi, A. A.; Mahran, M. R. H.; Lapib, M. Monatsh. Chem. 1999, 130, 1217.
27. Placin, F.; Clavier, G.; Najera, F.; Desvergne, J. P.; Pozzo, J. L. Polycycl. Aromat. Comput. 2000, 19, 107.
28. 2
29. Tol, E. B.; Ramesdonk, H. J.; Verhoeven, J. W.; Steemers, F. J.; Kerver, E. G.; Verboom, W.; Reinhoudt, D. N. Chem. Eur. J. 1998, 4, 2315.
30. A similar procedure has been described for the preparation of 1,10-phenanthroline-5,6-diamine; see: Bodige, S.; MacDonnell, F. M. Tetrahedron Lett. 1997, 38, 8159.