LARGE-SCALE SYNTHESIS OF THE HIGH-QUALITY INDOLOQUINONE ANTITUMOR AGENT EO-9 VIA [BIS(TRIFLUOROACETOXY)IODO]BENZENE OXIDATION OF 4-AMINOINDOLE

Authors
KINUGAWA M MASUDA Y ARAI H NISHIKAWA H OGASA T TOMIOKA S KASAI M
Citation
M. Kinugawa et al., LARGE-SCALE SYNTHESIS OF THE HIGH-QUALITY INDOLOQUINONE ANTITUMOR AGENT EO-9 VIA [BIS(TRIFLUOROACETOXY)IODO]BENZENE OXIDATION OF 4-AMINOINDOLE, Synthesis, (5), 1996, pp. 633
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
5
Year of publication
1996
Database
ISI
SICI code
0039-7881(1996):5<633:LSOTHI>2.0.ZU;2-N
Abstract
A convenient large scale preparation of the indoloquinone antitumor ag ent EO 9 (1) has been developed. The hazardous reagent, Fremy's salt, was replaced by a safer one, [bis(trifluoro acetoxy)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 th e reaction solvent for substitution of the methoxy group with ethyleni mine to introduce the aziridinyl group into EO 7 (6).