Pyridylethylation ofγ-carbolines

γ-Carbolines and their hydrogenated derivatives 3.* Hydrogenated derivatives of γ-carbolines: chemical and biological poperties (Review)

“…2-Alkyltetrahydro-γ-carbolines add readily to 2-and 4-vinylpyridine under the influence of metallic sodium in alcohol [15]. For 2-and 4-vinylpyridines the process can be realized with higher yields of the desired compounds in the DMSO-60% aqueous KOH system with tetrabutylammonium sulfate as phase-transfer catalyst [28].…”

“…Like normal anilines, 5-unsubstituted hexahydro-γ-carbolines undergo alkylation and acylation at the N(5) atom [13,14] and also pyridylethylation under the conditions of acid catalysis [15]. Attempts at the oxidation of hexahydro-γ-carbolines containing substituents at positions 5 or 8 to the corresponding tetrahydro derivatives by means of chloranil or palladium black were unsuccessful [13].…”

The synthesis and physiological activity of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles

“…The alkylation products, as a rule, are formed in good yields 69. E and Z isomers of 2122a,b were obtained by a long-lasting alkylation of indolyl-anions produced on treatment of compounds 121a,b with NaH in DMF by cinnamyl chloride.…”

Synthesis of hydrogenated 2,7-dimethylpyrrolo[3,4-b]indoles – analogs of dimebon

“…It is known that 2-alkyl--carbolines unsubstituted in the 5 and 8 positions readily take part in a Michael reaction in the presence of metallic sodium and add 2-and 4-vinylpyridines to give 5-(pyridinylethyl)--carbolines [19]. It was found later that the use of DMSO as solvent in this reaction leads to a powerful activation of the anions formed by the action of sodium or sodium hydride on 2-alkyl--carbolines.…”