ES398678A1 - Fused ring indole derivatives - Google Patents

Abstract

A procedure for preparing an indole derivative of the general formula (I) **(See formula)** in which R represents a hydroxyl, lower alkoxy, aryl-lower alkoxy, tetrahydropyranyloxy or acyloxy group, and R1 represents a monocyclic or bicyclic aryl radical or a group of aryl-lower alkyl, lower alkyl, lower alkenyl, lower alkynyl or amino-lower alkyl, O well R and R1 taken together represent an oxo, alkylencetal or di- (lower alkoxy) group; R2 and R5, which may be the same or different, represent hydrogen, hydroxy, lower alkyl, lower alkoxy, haloalkyl lower, halogen, amino or mono- or di (lower) alkyl-amino or, if R and R1 together represent a group of oxo, alkylencetal or di- (lower alkoxy), R2 and/or R5 may also represent nitro. R3 and R4 which may be the same or different, represent hydrogen or lower alkyl radicals, or R3 represents hydrogen and R4 represents hydroxyl; n represents 0, 1 or 2; the dashed line represents an optional link at the indicated position; and R6 which is present only when the optional bond represented by the broken line does not exist, represents hydrogen or a radical of aryl-lower alkyl, lower alkyl, lower alkenyl, lower alkynyl, amino-lower alkyl or acyl, or a quaternary ammonium or acid addition salt of said derivative, characterized in that, in a first phase, if desired, a subgeneric compound of the general formula (I) is hydrolyzed, in which R2, R3, R4, R5 and n they have the same meaning as before, while R and R1 together represent an alkylene cetal or di- (lower alkoxy) radical, or optionally, in this previous phase, a ketone of the general formula (III) is cyclized **(See formula)** in which R2, R3, R4, R5 and n have the same meaning as before and X is halogen, and, if desired, conversion of one group R2 and/or R5 into another group R2 and/or R5 by known methods; and, the product resulting from said optional preliminary phase, consisting of a ketone of the general formula (II) **(See formula)** in which R2, R3, R4, R5 and n have the same meaning as before, except that neither R2 nor R5 represent nitro, it is reacted with an organometallic compound, preferably a Grignard reagent type R1MgY, where Y is a halogen, an aryl lithium or sodium or potassium acetylide, and is as defined above and in a special case R1 represents a phenyl radical, halophenyl or alkylphenyl and more especially R2, R3, R4 and R5 each represent hydrogen atoms, the reagent of which allows the conversion of a ketone function into the group (see graph) and, if desired, alkylating or acylating the resulting compound, of formula (I), in which R represents a hydroxyl group and the dashed line represents a bond, to form a respective compound in which R represents a lower alkoxy, aryl-lower alkoxy, tetrahydropyranyloxy or acyloxy radical; in turn, if desired, converting the compound of the general formula (I) in which the dashed line represents a bond into a respective quaternary ammonium or acid addition salt; reduce, if desired, the compound in which the dashed line represents a bond, or its quaternary ammonium salt, to obtain a compound of formula (I) in which the bond represented by the dashed line does not exist and R6 represents an aryl-lower alkyl, lower alkyl, lower alkenyl, lower alkynyl or amino-lower alkyl group; converting the resulting compound, if desired, to a respective quaternary ammonium or addition salt; and, if desired, in any product convert a group R and/or R1 and/or R2 and/or R3 and/or R4 and/or R5 and/or R6 (if any) into another group R and/or R1 and/or R2 and/or R3 and/or R4 and/or R5 and/or R6 within the meanings defined above when dealing with formula (I) above. (Machine-translation by Google Translate, not legally binding)