T. V. Stupnikova

New nucleophilic substitution reactions in the indole series

The direct incorporation of residues of π-surplus heterocycles, CH acids, and inorganic anions in the indole ring was accomplished by the reaction of indole with various nucleophilic organic compounds in the presence of acylating agents.

Direct introduction of heterocyclic residues in the oxindole ring

It has been reported [1] that salts of some N-acyloxyheteroaromatic cations hetarylate 1-methyloxindole in situ. It seemed extremely probable that the salts of more electrophilic N-acylheteroaromatic cations also can be used for the direct introduction of a heterocyclic residue in the oxindole ring, especially since similar salts have proved to be suitable for the hetarylation of the most diverse CH acids with pKa ⩽ 20–21 [2].

DUAL REACTIVITY OF 1,2-DISUBSTITUTED DIHYDRO NITROGEN-HETEROAROMATIC SYSTEMS

Die disubstituierten Dihydropyridine (I), Dihydrochinoline (IV) und Dihydroisochin line (VI) reagieren mit Triphenylmethylkationen wie im Perchlorat (II) sowie analog auch mit Acetyl- und Triindolylmethylcarbonium-Kationen unter Abspaltung eines Hydridions oder des α-Substituenten und Bildung stabiler Pyridinium-, Chinoliniumund Isochinoliniumperchlorate (III), (V) und (VII).

Hetarylation of pyrazolones by salts of N-acylheteroaromatic cations

Isoquinoline, acridine, benzimidazole, and benzoxazole residues were introduced into the pyrazolone ring by reaction of N-heteroaromatic compounds with pyrazolones in the presence of acylating agents.