Regio-selective synthesis of 5-substituted 1H-tetrazoles using ionic liquid [BMIM]N-3 in solvent-free conditions: a click reaction

作者：Khaghaninejad Soheila; Heravi Majid M^*; Hosseinnejad Tayebeh; Oskooie Hossein A; Bakavoli Mehdi

来源：Research on Chemical Intermediates, 2016, 42(3): 1593-1610.

DOI：10.1007/s11164-015-2105-3

• Click reaction
• Ionic liquid: 1-butyl-3-methylimidazolium azide
• 5-Substituted 1H-tetrazoles
• Density functional theory
• Quantum theory of atoms in molecule
• Regio-selectivity

A multi-component, one pot and regio-selective synthesis of different 5-substituted 1H-tetrazoles was successfully accomplished via a click reaction. In this respect, we have performed the reaction of either isatins or various aromatic aldehydes with malononitrile and ionic liquid, 1-butyl-3-methylimidazolium azide ([BMIM]N-3), as a relatively green source of azide mediated by o-phthalimide-N-sulfonic acid (OPNSA). The calculated thermodynamic results demonstrate a reliable agreement with our experimentally observed regio-selectivity. From the electronic viewpoint, we have also assessed the nature of regio-selectivity via quantum theory of atoms in molecule analysis.
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• 出版日期2016-3