A series of previously unreported 2-alkyl-1-(2-chloromethylcarbonylethoxy)pyrroles have been synthesized via reaction of 2-alkly-1-(2-hydroxyethyl)pyrroles with chloroacetyl chloride and reaction of the intermediates with secondary amines to give 2-alkyl-1-[2-diethylamino(morpholino)methylcarbonylethoxy]pyrroles. Their antimicrobial activity has been studied. It is established that electron-accepting substituents in the methylcarbonylethoxy chain increase whereas electron-donating ones decrease the antimicrobial activity of the pyrroles in the order chlorine > morpholine > diethylamine.
Functionally substituted aromatic Schiff bases containing pyrrole and carborane fragments were synthesized by condensation of substituted benzaldehydes of the vanillin series with 2-(2-methyl-1H-pyrrol-1-yl)ethanamine and N-(3-aminophenyl)-o-carborane-1-carboxamide.Derivatives of nitrogen-containing polyhedral carborane cluster systems attract interest as substrates for pharmacokinetic studies in the field of boron neutroncapture therapy of cancer and radionuclide diagnostics and therapy [1][2][3][4][5][6]. It is also known that Schiff bases derived from substituted benzaldehydes of the vanillin series exhibit biological activity [7,8].The present communication reports on the synthesis of functionally substituted aromatic Schiff bases containing pyrrole (IIIa-IIId, IIIf) and carborane fragments (IIIe, IIIh, VIb-VIe, VIh, VIi) by condensation of substituted benzaldehydes Ia-Ii of the vanillin series with 2-(2-methyl-1H-pyrrol-1-yl)ethanamine (II) and N-(3-aminophenyl)-o-carboranecarboxylic acid (V) in boiling anhydrous methanol (Schemes 1, 2). The reactions were complete in 10-15 min under mild conditions in the absence of a catalyst, and compounds III and VI, including those containing two isomeric orthoand meta-carborane clusters in a single molecule (VIe, VIh) were isolated in 75-85% yield. Mild reaction
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