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Synthesis 1996; 1996(5): 633-636
DOI: 10.1055/s-1996-4270
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Large Scale Synthesis of the High Quality Indoloquinone Antitumor Agent EO 9 via [Bis(trifluoroacetoxy)iodo]benzene Oxidation of 4-Aminoindole

Masahiko Kinugawa, Yoshiaki Masuda, Hitoshi Arai, Hiroshi Nishikawa, Takehiro Ogasa, Shinji Tomioka, Masaji Kasai*
  • *Sakai Research Laboratories, Kyowa Hakko Kogyo Co. Ltd., 1-1-53, Takasu-cho, Sakai, Osaka 590, Japan, Fax +81(722)277214
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Publication Date:
31 December 2000 (online)

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A convenient large scale preparation of the indoloquinone antitumor agent EO 9 (1) has been developed. The hazardous reagent, Fremy’s salt, was replaced by a safer one, [bis(trifluoroacetoxy)iodo]benzene, for oxidation of the 4-aminoindole 3 to the corresponding indoloquinone 4, and high quality 1 was easily obtained by choosing acetonitrile as the reaction solvent for substitution of the methoxy group with ethylenimine to introduce the aziridinyl group into EO 7 (6).

EO 9 - antitumor agent - [bis(trifluoroacetoxy)iodo]benzene oxidation - indoloquinone - aziridinyl group