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Report | Regular issue | Vol 9, No. 11, 1978, pp.1607-1612
Published online, 1st January, 1970
DOI: 10.3987/R-1978-11-1607
A Synthetic Approach to the Mitomycins

Mitsuo Akiba, Yoshiyuki Kosugi, and Toyozo Takada*

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

The photo-induced reaction of 2-acetyl-3-[2-(4-bromopheny1)-2,3,4,7-tetraazabicyclo[3.3.0]oct-3-en-7-yl]-5-methyl-1,4-benzoquinone tosyl-hydrazone (1b) or 2-acetyl-3-[6-(4-bromophenyl)-3,6-diazabicyclo[3.1.0]hex-3-yl]-5-methyl-1,4-benzoquinone tosylhydrazone (1c) gave the hydroxyquinols (2a and b), which were converted to 1-(4-bromophenylimino)-6,9-dimethyl-5,8-dioxo-1H-pyrrolo[1,2-a]indole (5). 1-(4-bromophenylimino)-2,3-dihydro-6,9-dimethyl-5,8-dioxo-1H-pyrrolo[1,2-a]indole (6), 2-(4-bromophenylamino)-2,3-dihydro-6,9-dimethyl-5,8-dioxo-1H-pyrrolo[1,2-a]indole (7), and 1,2-disubstituted pyrrolo[l,2-a]indoloquinone (8) via the oxazolines (4a and b). These compounds, 6, 7, and 8, were also prepared in a one step synthesis by the thermal decomposition reaction of 1b.