Journal of Heterocyclic Chemistry p. 895 - 906 (1998)
Update date:2022-08-04
Topics:
Paul Krapcho
Gallagher, Cynthia E.
Hammach, Abdelhakim
Hacker, Miles P.
Menta, Ernesto
Oliva, Ambrogio
Domenico, Roberto Di
Re, Giovanni Da
Lotto, Andrea
Spinelli, Silvano
Synthetic routes have been developed which lead to ring-hydroxylated aza-analogues of antitumor anthrapyrazoles, namely, 2,5- bis[(aminoalkyl)amino] substituted 10-hydroxyindazo[3,4-fg]isoquinolin- 6(2H)-ones 1 and 7-hydroxyindazolo[4,3-gh]isoquinolin-6(2H)-ones 2. The regiospecific synthesis of 6,9-dihalo-4-hydroxybenz[g]isoquinolines 3 and 4 has been accomplished. Intermediate 3 was constructed in a multistep process involving Diels-Alder chemistry of benzolacrylates whereas 4 was assembled using Ni(II) mediated coupling of methyl 3-chloro-5-methoxyisonicotinate (15b) with the organic zinc reagent 18 derived from 2-fluoro-5-chlorobenzyl bromide (17). After protection of the hydroxy group with a p-methoxybenzyl moiety, the different nucleofugacities of the leaving groups present in 10 and 20 allowed sequential displacements by substituted hydrazines and amines, respectively, to lead to the desired p-methoxybenzyl protected analogues 12 and 22. Deprotection led to the side arm modified compounds 1 and 2. The displacements of 21a and 21b with N,N-dimethylethylenediamine also led to the tri[(aminoalkyl)amino]substituted analogues 23s and 23b, respectively, which arose from further S(N)Ar substitutions of the p-methoxybenzyloxy group.
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