Synthesis of benz[f]indole-4,9-diones via acetylenic derivatives of 1,4-naphthoquinone

Tetrahedron Letters

Volumn 50, Issue 49, 2009, Pages 6769-6771

  Shvartsberg, Mark S ^a   Kolodina, Ekaterina A ^a   Lebedeva, Nadezhda I ^a   Fedenok, Lidiya G ^a  

^a INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

Author keywords

3 Acetylamino 2 alkynyl 1,4 naphthoquinones; 3 Acetylamino 2 bromo 1,4 naphthoquinone; Benz f indole 4,9 diones; Cross coupling; Cyclization; Terminal acetylenes

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 3 ACETYLAMINO 2 ALKYNYL 1,4 NAPHTHOQUINONE DERIVATIVE; ACETYLENE DERIVATIVE; BENZENE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; SUBSTITUTION REACTION;

EID: 70350004074     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.110     Document Type: Article

References (20)

1. In: Sundberg R.J. (Ed). Indoles (1996), Academic Press, London
2. Lounasmaa M., and Tolvanen A. Nat. Prod. Rep. 17 (2000) 175-191
3. Somei M., and Yamada F. Nat. Prod. Rep. 21 (2004) 278-311
4. Kawasaki T., and Higuchi K. Nat. Prod. Rep. 22 (2005) 761-793
5. Higuchi K., and Kawasaki T. Nat. Prod. Rep. 24 (2007) 843-868
6. Ishikura M., and Yamada K. Nat. Prod. Rep. 26 (2009) 803-852
7. Evans B.E., Rittle K.E., Bock M.G., DiPardo R.M., Freidinger R.M., Whitter W.L., Lundell G.F., Veber D.F., Anderson P.S., Chang R.S.L., Lotti V.J., Cerino D.J., Chen T.B., Kling P.J., Kunkel K.A., Springer J.P., and Hirshfield J. J. Med. Chem. 31 (1988) 2235-2246
8. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893-930
9. Cacchi S., and Fabrizi G. Chem. Rev. 105 (2005) 2873-2920
10. Humphrey G.R., and Kuethe J.T. Chem. Rev. 106 (2006) 2875-2911
11. Romanov V.S., Moroz A.A., and Shvartsberg M.S. Izv. Akad. Nauk SSSR, Ser. Khim. (1985) 1090-1094 (Bull. Acad. Sci. USSR, Div. Chem. Sci. 1985, 34, 994-997)
12. Gritsan N.P., Shvartsberg V.M., Romanov V.S., and Shvartsberg M.S. Izv. Akad. Nauk SSSR, Ser. Khim. (1984) 469 (Bull. Acad. Sci. USSR, Div. Chem. Sci. 1984, 33, 433)
13. Shvartsberg M.S., Barabanov I.I., and Fedenok L.G. Usp. Khim. 73 (2004) 171-196 (Russ. Chem. Rev. 2004, 73, 161-184)
14. -11628, 1669, 1695 (C{double bond, long}O), 3432 (NH).
15. Rossi R., Carpita A., and Bellina F. Org. Prep. Proced. Int. 27 (1995) 127-160
16. Yasuhara Y., Kanamori Y., Kaneko M., Numata A., Kondo Y., and Sakamoto T. J. Chem. Soc., Perkin Trans. 1 (1999) 529-534
17. Ivashkina N.V., Yakovleva E.A., Ivanchikova I.D., Moroz A.A., and Shvartsberg M.S. Izv. Akad. Nauk, Ser. Khim. (2005) 1465-1469 (Russ. Chem. Bull., Int. Ed. 2005, 54, 1509-1513)
18. Inoue A., Kuroki N., and Konishi K. Soc. Org. Synth. Chem. 16 (1958) 603-609 Chem. Abstr. 1959, 53, 3233
19. Ivashkina N.V., Romanov V.S., Moroz A.A., and Shvartsberg M.S. Izv. Akad. Nauk SSSR, Ser. Khim. (1984) 2561-2565 (Bull. Acad. Sci. USSR, Div. Chem. Sci. 1984, 33, 2345-2348)
20. Yakovleva E.A., Ivanchikova I.D., and Shvartsberg M.S. Izv. Akad. Nauk, Ser. Khim. (2005) 412-418 (Russ. Chem. Bull., Int. Ed. 2005, 54, 421-427)