First straightforward synthesis of 2,4-disubstituted benz[g]isoquinoline-3,5,10(2H)-triones, 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones

Tetrahedron

Volumn 64, Issue 32, 2008, Pages 7545-7554

  Jacobs, Jan ^a   Kesteleyn, Bart ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

2 Azaanthraquinones; Benz g isoquinoline 3,5,10(2H) triones; Quinones

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2 N BUTYL 4 CYANOBENZ[G]ISOQUINOLINE 3,5,10(2H) TRIONE; 3 ETHOXYCARBONYL 2 ETHYLAMINO 5 ISOPROPYLNAPHTHO[3,2,1-DE] ISOQUINOLINE 4,7 DIONE; 3 ETHOXYCARBONYL 5 ISOPROPYL 2 ISOPROPYLAMINONAPHTHO[3,2,1 DE]ISOQUINOLINE 4,7 DIONE; 3 ETHOXYCARBONYL 5 ISOPROPYL 2 N PROPYLAMINONAPHTHO[3,2,1 DE]ISOQUINOLINE 4,7 DIONE; 4 CYANO 2 ISOBUTYLBENZ[G]ISOQUINOLINE 3,5,10(2H) TRIONE; 4 CYANO 2 ISOPROPYLBENZ[G]ISOQUINOLINE 3,5,10(2H) TRIONE; 5 ISOPROPYL 2 ISOPROPYLAMINO 3 METHYLNAPHTHO [3,2,1 DE]ISOQUINOLINE 4,7 DIONE; 5 ISOPROPYL 2 N PROPYLAMINO 3 METHYLNAPHTHO [3,2,1 DE]ISOQUINOLINE 4,7 DIONE; 5 ISOPROPYL 3 METHYL 2 PYRROLIDINYLNAPHTHO [3,2,1 DE]ISOQUINOLINE 4,7 DIONE; 5 N BUTYL 2 ETHYLAMINO 3 METHOXYCARBONYL 1 METHYLNAPHTHO[3,2,1 DE]ISOQUINOLINE 4,7 DIONE; 5 N BUTYL 3 METHOXYCARBONYL 2 N PROPYLAMINONAPHTHO[3,2,1 DE]ISOQUINOLINE 4,7 DIONE; 5 N PROPYL 2 N PROPYLAMINO 3 METHYLNAPHTHO [3,2,1 DE]ISOQUINOLINE 4,7 DIONE; 6 ISOPROPYLBENZO[H]PYRIDO[3,4,5 KL] 1,2,3,4 TETRAHYDROACRIDINE 5,8 DIONE; ETHYL 3 ETHYLAMINOBUT 2 ENOATE; ETHYL 3 N PROPYLAMINOBUT 2 ENOATE; ISOQUINOLINE DERIVATIVE; METHYL 3 AMINOBUT 2 ENOATE; METHYL 3 ETHYLAMINOPENT 2 ENOATE; METHYL 3 N PROPYLBUT 2 ENOATE; N ISOPROPYLCYCLOPENTYLIDENEAMIN; N N PROPYLCYCLOHEPTYLIDENEAMINE;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; PRIORITY JOURNAL; SYNTHESIS;

EID: 45649084366     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.111     Document Type: Article

References (35)

1. Solis P.N., Lang'at C., Gupta M.P., Kirby G.C., Warhurst D.S., and Phillipson J.D. Planta Med. 61 (1995) 62-65
2. Phillipson J.D. Phytochemistry 38 (1995) 1319-1343
3. Okunade A.L., Clark A.M., Hufford C.D., and Oguntimein B.O. Planta Med. 65 (1999) 447-448
4. Nok A.J. Cell Biochem. Funct. 20 (2002) 205-212
5. Chem. Abstr. (2002) 636119
6. Arsenault G.P. Tetrahedron Lett. 6 (1965) 4033-4037 and references therein
7. Parisot D., Devys M., and Barbier M. Z. Naturforsch. 44 (1989) 1473-1474
8. Parisot D., Devys M., and Barbier M.Z. Phytochemistry 29 (1990) 3364-3365
9. Gräfe U., Ihn W., Tresselt D., Miosga N., Kaden U., Schlegel B., Bormann E.-J., Sedmera P., and Novak J. Biol. Met. 3 (1990) 39-44
10. Miljkovic A., Mantle P.G., Williams D.J., and Rassing B. J. Nat. Prod. 64 (2001) 1251-1253
11. Moriyasu Y.K., Miyagawa H., Hamada N., Miyawaki H., and Ueno T. Phytochemistry 58 (2001) 239-241
12. Parisot D., Devys M., and Barbier M. J. Antibiot. 42 (1989) 1189-1190
13. Steyn P.S., Wessels P.L., and Marasas W.F.O. Tetrahedron 35 (1979) 1551-1555
14. Visconti A., Surico G., Iacobellis N.S., and Bottalico A. Phytopath. Medit. 22 (1983) 122-156
15. Waterman P.G., and Muhammad I. Phytochemistry 24 (1985) 523-527
16. Peterson J.R., Zjawiony J.K., Liu S., Hufford C.D., Clark A.M., and Rogers R.D. J. Med. Chem. 35 (1992) 4069-4077
17. Kobayashi J., Cheng J., Nakamura H., Ohizumi Y., Hirata Y., Sasaki T., Ohta T., and Nozoe S. Tetrahedron Lett. 29 (1988) 1177-1180
18. Feliu L., Ajana W., Alvarez M., and Joule J.A. Tetrahedron 53 (1997) 4511-4520
19. Alvarez M., Feliu L., Ajana W., Joule J.A., and Fernandez-Puentes J.L. Eur. J. Org. Chem. (2000) 849-855
20. Carneiro do Nascimento S., Bouammali B., Boitard M., Pautet F., Soufiaoui M., and Fillion H. Pharmazie 49 (1994) 702-703
21. Jacobs J., Claessens S., Kesteleyn B., Huygen K., and De Kimpe N. Tetrahedron 63 (2007) 2503-2510
22. Baraldi P.G., Simoni D., and Manfredini S. Synthesis (1983) 902-903
23. Hayes B.L. Microwave Synthesis, Chemistry at the Speed of Light (2002), CEM, Matthews, NC pp 292
24. Gabriel C., Gabriel S., Grant E.H., Halstead B.S.J., and Mingos D.M.P. Chem. Soc. Rev. 27 (1998) 213-223
25. Weingarten H., Chupp J.P., and White W.A. J. Org. Chem. 32 (1967) 3246-3249
26. Fraser R.R., Banville J., Akiyama F., and Chuaqui-Offermanns N. Can. J. Chem. 59 (1981) 705-709
27. Liao S., and Collum D.B. J. Am. Chem. Soc. 125 (2003) 15114-15127
28. Ma Y., Lobkovsky E., and Collum D.B. J. Org. Chem. 70 (2005) 2335-2337
29. Brandt C.A., da Silva A.C.M.P., Pancote C.G., Brito C.L., and da Silveira M.A.B. Synthesis (2004) 1557-1559
30. Zhang Z.-H., and Song L.M. J. Chem. Res. (2005) 817-820
31. Zhang Z.-H., Yin L., and Wang Y.M. Adv. Synth. Catal. 348 (2006) 184-190
32. Iwanami M., Shibanuma T., Fujimoto M., Kawai R., Tamazawa K., Takenaka T., Takahashi K., and Murakami M. Chem. Pharm. Bull. 27 (1979) 1426-1440
33. Litvic M., Filipan M., Pogoreli I., and Cepanec I. Green Chem. 7 (2005) 771-774
34. AIST: Integrated Spectral Database System of Organic Compounds (Japan).
35. Anderson P.C., and Staskun B. J. Org. Chem. 30 (1965) 3033-3037