A new synthesis of pyrrolo [1,2-a]indoloquinone and related compound

✍ Scribed by T. Takada; Y. Kosugi; M. Akiba

• Book ID: 104243007
• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 180 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)91885-4

✦ Synopsis

In the synthetic studies on mitomycin antibiotics 0, up to the present, a number of indoloquinones which lack the aziridino group or ring A have been prepared M mitomycin analoguee. ') In this paper we wish to deecribe a novel route to pyrrolo(l,Z-a]indoloquinone and related compouud~ which seem to posseaa the same biological activities aa those of dtomycin and the requisite akeleton for further elaboration. Tolrylhydrazone Q (n.p. 242') prepared from dihydrozyacetophenone 2 uaa oxidized with potassium nitroeodisulfonate in water -ethanol affording quinone 4 (decomp. 147-150°) in high yielda ( KL9C$). On treatment with excees amine8 (pyrrolidine, piperidine and morpholine) in chloroform, 4. furnished aminoquinones 1(+ decomp. 124-125'; i.r. 3050 ($Si), 1670. 1660 (XEO), 1528 (&=I!-CLO) cm-l; n.m.r. (CDCl3)h 1.47-1.87 (48, II, -CH2CE2-), 1.95 (3E, d, J = 1.8 Hz, C&$~S), 2.03 ( z, s,C+=M,2.40 (3% s, -C$), 3.12-3.54 (Sa, m, 2 -CH21i<), 6.40 @.I, q, J = 1.8 Hz, Q-!Z=&-C$), 7.25 @I, d, J = 8 Hz, aromatic proton), 7.80 (2& d, J = 8 Hz, aromatic proton); a, decomp.