Method for preparing 1-chloro-5-alkylisoquinolines condensed wit

Details Method for preparing 1-chloro-5-alkylisoquinolines condensed wit Method for preparing 1-chloro-5-alkylisoquinolines condensed wit

1988-11-14

1990-10-30

Sham, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 70, 546 77, 546 79, 546 80, 546101, C07D22108, C07D22118, C07D47114, C07D49504

Patent

active

049669710

ABSTRACT:
To prepare the compound (I), a lithiation of the compound (II) is performed, an aldehyde (IV) is reacted with the compound (III) formed, leading to the secondary alcohol (V) which is subjected to a reduction leading to the compound (VI), which is then subjected to a hydrolysis (of the dioxolane group)/cyclization/dehydration reaction. The procedure may be followed by a nucleophilic substitution reaction of the chlorine. The compounds (a) below exhibit antitumor activity. ##STR1## R=C.sub.1 -C.sub.3 alkyl; Ar=aromatic or polycyclic aromatic group; R.sub.1 and r.sub.2 =H or C.sub.1 -C.sub.3 alkyl; and n=2 to 4. No drawing.

REFERENCES:
Croisy-Delcey et al., J. Org. Chem. vol. 53 (22) pp. 5301-5304 (1988).
LaMottina, J. Het. Chem., vol. 20 pp. 533-538 (1983).
Barton et al. J. Chem. Soc. Perkin Trans I, (5) pp. 503-507 (1976).
Lown et al., Can. J. Chem., vol. 48 (2) pp. 327-335 (1970).

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