Zur protonenkatalysierten Xanthenylierung von Tryptamin, Nω-Acetyltryptamin und Gramin: Ein Beitrag zur Konstitutionsaufklärung in der Indol-Analytik

Regioselective proton-catalyzed diarylmethylation of indoles with 9H-xanthydrol, dibenzosuberenol, and bis[4-dimethylaminophenyl]methanol

3-Isopropylindole (4) is xanthenylated both at N-1 (stereocontrolled major reaction), C-2, and on the phenyl nucleus of the indole skeleton by xanthydrol (1). Other carbinols such as dibenzosuberenol (2) and bis[4-dimethylaminophenyl]methanol (3) with lower electrophilic SN1 activities than 1 do not react with 4 but do react very selectively with simple methylindoles to form diarylmethylated derivatives.

Mechanismus und Reaktionswege der Xanthenylierung an ambidenten nukleophilen Arzneistoffen

Am Beispiel der ambidenten nukleophilen Arzneistoffe 4-Aminobenzolsulfonamid (3), Indometacin (7) und Phenylbutazon (10) werden Aralkylierungen mit dem SN1-aktiven Reagens Xanthydrol (1) vorgestellt. Mechanism and Reaction Path of the Xanthenylation of Ambident Nucleophilic Drugs The aralkylation of ambident nucleophilic drugs, e.g. 4-aminobenzenesulfonamide (3), indometacine (7) and phenylbutazone (10), with SN1-active xanthydrol (1) is described.

ChemInform Abstract: Regioselective Proton-Catalyzed Diarylmethylation of Indoles with 9H-Xanthydrol, Dibenzosuberenol, and Bis(4-dimethylaminophenyl)methanol.

3-Isopropylindole (4) is xanthenylated both at N-1 (stereocontrolled major reaction), C-2, and on the phenyl nucleus of the indole skeleton by xanthydrol (1). Other carbinols such as dibenzosuberenol (2) and bis[4-dimethylaminophenyl]methanol (3) with lower electrophilic SN1 activities than 1 do not react with 4 but do react very selectively with simple methylindoles to form diarylmethylated derivatives.