Abstract

BELLO, Josué S et al. Simple preparation of new N-aryl-N-(3-indolmethyl) acetamides and their spectroscopic analysis. Univ. Sci. [online]. 2009, vol.14, n.3, pp.216-224. ISSN 0122-7483.

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 monitored by thin layer chromatography over Silufol UV₂₅₄ 0.25 mm-thick chromatoplates. Product isolation and purification were performed by column chromatography (SiO₂), using ethyl acetate-petroleum ether mixtures as eluents. Results. The synthesis of new N-aryl-N-(3-indolmethyl) acetamides based on first step iminization reaction of indol-3-carbaldehyde is accomplished. The structures of the C-3 substituted indoles were confirmed by ¹H-NMR and ¹³C-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.

Keywords : indole; acetamides; iminization.

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