Synthesis of potential antineoplastic agents. XXVII. (Reissert compound studies. XLIV.). The ellipticine reissert compound as an intermediate in the syntheses of ellipticine analogs

Abstract

Mit Trimethylsilylcyanid (II) und Säurechloriden (III) entstehen aus den Isochinolinen (I) glatt die Reissert‐Verbindungen (IV), die zu (V) alkyliert werden können.

Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5,6,11-trimethyl-5H-benzo[b]carbazole.

“…The mechanism of the reaction of isoquinoline-N-oxide (5) to 6 with p-TosCl has been extensively investigated using p-TosC1 labelled with t*O and it is assumed that the rearrangement proceeds via an intimate ion pair (8) since almost no scrambling of the isotopes was observed (Scheme 2).tsJ6Afte.r reaction of the tosylgroup with the N-oxide function of 5 to 6 the chloride-ion adds to C-l (7) whereafter the tosyloxygroup shifts to C-4 (9) via 8 retaining its stereochemical structure. Finally hydrochloric acid eliminates from 9 to give 4-tosylisoquinoline (10).…”

Pharmacologically Active Secondary Metabolites from Wood

“…Ellipticine, 7, and a number of its derivatives, especially quaternized derivatives, show great promise as antitumor agents (832). These derivatives are of interest in the NCI program in the United States and even more so in France.…”