Current Organic Chemistry

Author(s): Abbas Azimi-Roshan*, Hamzeh Kiyani* and Manouchehr Mamaghani

DOI: 10.2174/0113852728269992241030054239

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Green Pseudo-seven Component Synthesis of Tris-cyclohexylamino-oxo-benzene- 1,3,5-tricarboxylates via Passerini Reaction under Aqueous Conditions

Page: [1057 - 1065] Pages: 9

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Abstract

In this study, a simple, mild, and environmentally friendly process was used for the pseudo-seven component reaction between readily available benzene-1,3,5- tricarboxylic acid, isocyano-cyclohexane, and various aldehydes. This rapid method produced the tris-cyclohexylamino-oxo-benzene-1,3,5-tricarboxylates in relatively acceptable and more reasonable reaction times (10-15 min) and high achievable efficiencies (85-95%) by employing a Passerini reaction. Water was used as an eco-friendly and low-cost solvent for the green synthesis of benzene tris-carboxamides. The reactions were carried out via a Passerini approach at 50ºC for relatively shorter reaction times. The antibacterial action of the synthetic tris-carboxamides was investigated, and some of them gave satisfactory and promising antibacterial results. Target tris-Passerini molecules recrystallized from 96% EtOH. The structures of the resulting molecules were evaluated and confirmed with the help of spectral data and elemental analyses.

Keywords: Tris-cyclohexylamino-oxo-benzene-1, 3, 5-tricarboxylate, Passerini approach, benzene-1, 5-tricarboxylic acid, aqueous conditions, green synthesis, antibacterial activity.