Acylation, cyanoethylation and alkylation of methyl and phenyl indolylmagnesium salts: Influence of the substituents on the c‐ and N‐reaction products

Abstract

Analysis of the influence of the substitution on indolylmagnesium salts in the reaction with benzoyl chlo ride, acrylonitrile and methyl iodide, giving the C‐ and N‐derivatives, have been carried out. The yield in the C‐ and N‐product depends upon the electronic character and position of the substituent (methyl or phenyl) on the indole ring and of the ethereal solvent as well as the concentration and molar ratio of the reagents. The 2‐ or 3‐phenyl substituted indolylmagnesium salts with acrylonitrile always gave the 1‐(2‐cyanoethyl)indole derivative.

Synthesis of 2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepines and 11-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indoles

“…Condensation reaction of (1-hydroxymethyl)benzotriazole with 3-(pyrrol-1-yl)-1-propylamine (1) 16 (Scheme 3) and 3-(3-methyl-indol-1-yl)-propylamine (7) [17][18][19] (Scheme 4) in chloroform in the presence of trace amounts of p-toluene sulphonic acid formed 2 and 8 in 55% and 51% yield respectively. The product was fully characterized by 1 H and 13 C NMR spectra.…”

Studies with azoles and benzoazoles: A novel simple approach for synthesis of 3‐functionally substituted 3‐acylindoles

“…ir spectra were recorded in KBr pellets with Satellite 2000 spectrophotometer. 1 H nmr and 13 C nmr spectra were recorded on a Bruker AC-300 300 MHz spectrometer in DMSO-d6 and CDCl 3 as solvents and Tms as internal standard; chemical shifts are reported in units (ppm). Mass spectra were measured at 70 eV using shimadzu GCms-QP 1000 EX spectrometer.…”

“…3-Substituted indoles are important heterocycles both in nature as well as pharmaceuticals [1,2]. For example tryptophane 1 and indole-3-acetaldoxime 2 participate in vital biological processes [3] while sumatriptan 3 is used for migraine treatment [4].…”

“…1 General method for preparation of compounds 20a-f. To a solution of each of 15a,b (1.45 g, 5 mmol) in a mixture of DMF (2 mL) and triethylamine (10 mL) was added the appropriate chloro derivative 19a-c (10 mmol). The reaction mixture was refluxed for 40 min and left to cool to r.t.…”

KF/Al2O3 Mediated Aza-Michael Addition of Indoles to Electron-Deficient Olefins

“…c All products were characterized by m.p, IR, 1 H NMR, MS and the physical data were similar to those reported in the literature[22][23][24][25][26][27][28][29][30][31].…”