Abstract
Objectives. To prepare new indolic molecules and characterize them by spectroscopic methods. Materials and methods: All reagents were purchased from Aldrich, commercial grade. The purity of the products and the composition of the reaction mixtures were mon itored by thin layer chromatography over Silufol UV 254 0.25 mm-thick chromatoplates. Product isolation and purification were performed by column chromatography (SiO 2 ), using ethyl acetate-petroleum ether mixtures as eluents. Results. The synthesis of new N-aryl-N-(3indolmethyl) acetamides based on first step iminization reaction of indol-3-carbaldehyde is accomplished. The structures of the C-3 substituted indoles were confirmed by 1 H-NMR and 13 C-NMR studies supported by inverse-detected 2D NMR experiments and also through monocrystal X-ray diffraction. Conclusions. An efficient, economic, and fast synthetic route was designed to the construction of the N-aryl-N-(3-indolmethyl) acetamides, structural analogues of some alkaloids.
Highlights
The research of the indol chemistry has been and still is one of the most active areas of heterocyclic chemistry
We were interested in 3-indolylmethanamine derivatives molecules that could serve as useful precursors to many drug-like indolic compounds in our quest for compounds with antiparasitic properties.[12,13,14]
N-(2-cyanophenyl)-N-(3indolylmethyl)amine (7) was prepared as a white solid in 70 % yields after purification through recrystallization (Figure 2). Since this amine has interesting structural elements to use in the synthesis of different indolic heterocycles, we studied its acetylation reaction with acetic anhydride
Summary
The research of the indol chemistry has been and still is one of the most active areas of heterocyclic chemistry. The Mannich reaction[6,7] and the catalyzed Friedel-Crafts alkylation reactions of indoles[8,9,10,11] are considered as a powerful carboncarbon bond process to afford the 3-indolylmethanamine derivatives 1. Another synthetic route to these compounds by using 3-indolcarboxyaldehyde via its imino derivatives formation is valid. The results of our investigation on preparation, spectral and structural characterization of new two acetamides based on 3-indolyl methanamine motif are reported in this work
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