Fused isoquinoline derivatives

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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260283S, 260289C, 424258, C07D47114, C07D49514, C07D51314

Patent

active

041137310

ABSTRACT:
Fused isoquinoline derivatives of the general formula ##STR1## wherein: A is a divalent radical selected from the groups ##STR2## wherein R.sub.3 and R.sub.4 each independently represents hydrogen, alkyl,, alkenyl, cycloalkyl, aryl, aralkyl, aralkenyl, cycloalkyl-alkyl or, taken together with the adjacent double bond, represent a cycloalkene containing from 5 to 8 carbon atoms or an aromatic nucleus;
R.sub.5 represents hydrogen, hydroxyl, alkyl, alkenyl, cycloalkyl, aryl, aralkyl, aralkenyl or cycloalkyl-alkyl;
Y is .dbd.O, .dbd.S or .dbd.NH;
X is --O--, --S-- or --NR.sub.6 -- wherein R.sub.6 represents hydrogen, alkyl, cycloalkyl, aryl, aralkyl or cycloalkyl-alkyl;
R.sub.1 and R.sub.2 each independently represents hydrogen, alkyl, phenyl, cycloalkyl, alkoxy, alkenyloxy, methylenedioxy, cycloalkoxy, halo or di-alkylamino or, taken together with the adjacent carbon atoms of the benzene ring, form a cycloalkenyl group containing 5 or 6 carbon atoms or an aromatic nucleus fused on the benzene ring. The compounds are essentially prepared through thermal cyclization of a compound of the formula ##STR3## wherein A, X, Y, R.sub.1 and R.sub.2 have the same meanings given before, with the proviso that R.sub.1 and R.sub.2 cannot simultaneously occupy both the ortho positions, B represents hydrogen, R represents an --OR.sub.7 or --NR.sub.8 R.sub.9 radical wherein R.sub.7 is alkyl, aryl or aralkyl and R.sub.8 and R.sub.9 each independently represents hydrogen, alkyl, aryl, aralkyl, or taken together with the adjacent nitrogen atom represent a heterocyclic saturated radical of 5 or 6 atoms which may contain a further hetero-atom selected from oxygen and nitrogen, or the symbols B and R taken together represent a further bond between the adjacent carbon and nitrogen atoms.

REFERENCES:
patent: 3630745 (1971-12-01), Beavers et al.
patent: 3644366 (1972-02-01), Jeanmart et al.
patent: 3663551 (1972-05-01), Deryckere et al.
Goodman et al, The Pharmacological Basis of Therapeutics (1965) pp. 37-43.
Bailey et al., Chemical Abstracts 51 417a (1957).
Ried et al., Chemical Abstracts, 64, 695a (1966).
Mohunta et al., J. Chem. Soc. (1934), pp. 1263-1264.
Winters et al., Chemical Abstracts, vol. 84, 43,930e (1976) of paper in Tetrahedron Letters (44) 3877-3878 (1975).

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