Synthesis of 1N-aryl-2-methyl-3-ethoxycarbonyl-pyridino [2,3-f]indole-4,9-dione derivatives (II)

1N-아릴-2-메틸-3-에톡시카르보닐-피리디노 [2,3-f]인돌-4,9-디온 유도체의 합성 (II)

  • 서명은 (이화여자대학교 약학대학) ;
  • 박희경 (이화여자대학교 약학대학)
  • Published : 1997.10.01

Abstract

The 6.7-dichloroquinoline-5,8-dione (I) was reacted with ethyl acetoacetate in the presence of sodium ethoxide to yield 6-(${\alpha}$-acetyl-${\alpha}$-ethoxycarbonyl methyl)-7-chloro-qui noline-5,8-dione(II). When this compound II was reacted with some arylamine (phenyl, p-toluyl, p-fluorophenyl, p-chlorophenyl. p-bromophenyl, p-iodophenyl, p-trifluoromethylphenyl, p-dimethylaminophenyl,indanyl), 1N-aryl-2-methyl-3-ethoxycarbonyl pyridino[2,3-f]-indole-4.9-dione(IIIa-I) were obtained via intramolecular cyclization.

Keywords

References

  1. Can. J. Biochem. v.34 The mechanism of the degradation of DNA by streptonigrin. Cone, R.;Hasen, K.;Lown, J. W.;Morgan, A. R.
  2. J. Med. Chem. v.29 Streptonigrin : Structure-activity relationship among simple bicycle analogues. Johnson, F.;Shaih, I. A.;Grollmann, A. P.
  3. J. Mol. Bio. v.206 DNA-Drug Interactions : The crystal structure of d(CCGATCG) complexed with daunomycin. Moore, M. H.;Hunter, W. H.;Kennard, O.
  4. J. Nat. Prod. v.50 Reverse phase flash chromatography : A method for the rapid partitionary of nature product extract. Blunt, J. W.;Calden, V. L.
  5. C. J. Am. Chem. Soc. v.114 Total synthesis of discorhabdin Kita, Y.;Thoma, H.
  6. Yakhak Hoeji v.34 Synthesis of Benzo (f)-indole-4,9-dione Derivatives. Lee, J. Y.;Suh, M. E.
  7. Arch. Pham. v.312 Synthesis und Reduction von Benzo(f) indol-4.9-dion Derivaten. Kukulander, U.
  8. Yakhak Hoeji v.40 Synthesis of 1Nalky1-2-methyl-3-ethoxycarbonyl-pyridino-(2,3f) inodole-4,9-dione Derivatives Suh, M. E.;Park, H. K.
  9. Zh. Prikl. Khim(Lening rad). v.49 Nucleophilic substitution of 6,7-dichloroquinoline-5,8-quinone. Klimovich, O. S.;Kolesnikou U. T.