Synthesis of some phenolic and amino derivatives of cinchoninic acid

Abstract EN

Treatment of cinchoninic acids (1a,b) with allyl bromide afforded compounds (2a,b), and the hydrolysis of (2a) gave the 2-(4`-allyloxyphenyl) cinchoninic acid (4) .

Glycedylation of compound (1a) afforded compound (3a), while glycedylation of compound (1b) gave compounds (3b) and (3bb).

The acetylation of the acids (1a,b) gave the acetyl derivatives (5a,b) .

Benzylation of the amino compound (1b) with m-fluorobenzyl chloride afforded compound (6) .

The reaction of compounds (1a,b) with allyl isothiocyanate or amino compound with carbon disulfide afforded thiocarbamate (7a), thiourea (7b) and dithiocarbamic acid (8) which is used as a synthone to prepare allylic ester of dithiocarbamate (9) respectively .

Finally Compound (1b) can be transformed to a glycene derivative of cinchoninic acid (10).

The synthesized compounds were confirmed by the physical and spectral means in addition to the functional groups systematic identification .