Synthesis of seven- and eight-membered [1,2-a] alicyclic ring-fused benzimidazoles and 3-aziridinylazepino[1,2-a]benzimidazolequinone as a potential antitumour agent

Tetrahedron Letters

Volumn 49, Issue 36, 2008, Pages 5235-5237

  Fahey, Karen ^a   Aldabbagh, Fawaz ^a  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

Annulations; Antitumour agents; Diazoles; Heterocycles

Indexed keywords

3 AZIRIDINYLAZEPINOL[1,2 A]BENZIMIDAZOLEQUINONE; ANTINEOPLASTIC AGENT;

ACETYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG OXIDATION; DRUG POTENCY; DRUG SYNTHESIS; HYDROGENATION; NITRATION;

EID: 47549106283     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.121     Document Type: Article

References (28)

1. Skibo E.B., Islam I., Schulz W.G., Zhou R., Bess L., and Boruah R. Synlett (1996) 297
2. Zhou R., and Skibo E.B. J. Med. Chem. 39 (1996) 4321
3. Craigo W.A., LeSueur B.W., and Skibo E.B. J. Med. Chem. 42 (1999) 3324
4. Suleman A., and Skibo E.B. J. Med. Chem. 45 (2002) 1211
5. O'Shaughnessy J., and Aldabbagh F. Synthesis (2005) 1069
6. Lynch M., Hehir S., Kavanagh P., Leech D., O'Shaughnessy J., Carty M.P., and Aldabbagh F. Chem. Eur. J. 13 (2007) 3218
7. Hehir S., O'Donovan L., Carty M.P., and Aldabbagh F. Tetrahedron 64 (2008) 4196
8. Saunders K.H. J. Chem. Soc. (1955) 3275
9. Nair M.D., and Adams R. J. Am. Chem. Soc. 83 (1961) 3518
10. DeSelms R.C. J. Org. Chem. 27 (1962) 2165
11. Meth-Cohn O., and Suschitzky H. J. Chem. Soc. (1963) 4666
12. Freedman A.R., Payne D.S., and Day A.R. J. Heterocycl. Chem. 3 (1966) 257
13. Suschitzky H., and Sutton M.E. Tetrahedron 24 (1968) 4581
14. Möhrle H., and Gerloff J. Arch. Pharm. 311 (1978) 381
15. Caroon J.M., and Fischer L.E. Heterocycles 32 (1991) 459
16. Anastasiou D., Campi E.M., Chaouk H., and Jackson W.R. Tetrahedron 48 (1992) 7467
17. Haque M.R., and Rasmussen M. Tetrahedron 53 (1997) 6937
18. Aldabbagh F., and Bowman W.R. Tetrahedron 55 (1999) 4109
19. McClure J.R., Cluster J.H., Schwarz D.H., and Lill D.A. Synlett (2000) 710
20. Nazarenko E.G., Shyrokaya T.I., Shvidenko E.V., and Tolmachev A.A. Synth. Commun. 33 (2002) 4303
21. Gagosz F., and Zard S.M. Org. Lett. 4 (2002) 4345
22. Allin S.M., Bowman W.R., Karim R., and Rahman S.S. Tetrahedron 62 (2006) 4306
23. 2O: C, 73.01; H, 7.88; N, 12.16. Found: C, 72.73; H, 7.67; N, 12.42.
24. 3: C, 59.76; H, 5.79; N, 16.08. Found: C, 59.68; H, 6.17; N, 15.76. The second fraction eluted was 3-methoxy-2-nitro-7,8,9,10-tetrahydro-6H-azepino[1,2-a]benzimidazole 11 (43 mg, 35%) as a yellow solid.
25. 3), 96.53 (CH), 109.20 (CH), 127.67 (C), 131.49 (C), 131.86 (C), 141.09 (C), 156.29 (Ar-5a-C) ppm.
26. Allen C.F.H., Spangler F.W., and Webster E.R. Org. Synth. Colloid 4 (1963) 433
27. 2: C, 65.34; H, 5.88; N, 16.34. Found: C, 65.64; H, 5.51; N, 16.85.
28. 1H NMR correlation was also carried out on compound 4.