Piperazine: An excellent catalyst for the synthesis of 2-amino-3-cyano-4H-pyrans derivatives in aqueous medium

Bioorg Chem. 2018 Dec:81:326-333. doi: 10.1016/j.bioorg.2018.08.026. Epub 2018 Aug 23.

Abstract

An improved, forthright, and highly efficient one-pot synthesis of a wide range of pharmaceutically exciting diverse kind of functionalized 2-amino-3-cyano-4H-pyrans and especially bis-pyrans compounds is developed using piperazine as a low-cost and environmentally benign commercially available basic catalyst in aqueous media. The attractive features of this process are simple procedure, short reaction times, high yields, no column chromatographic separation and commercial availability and recyclability of the catalyst. Also, piperazine can catalyze the synthesis of the target compounds on a larger scale. Furthermore, rational mechanism was suggested via GC-Mass analysis of the trapped intermediates.

Keywords: 2-amino-3-cyano-4H-pyrans; Aqueos medium condition; Basic catalyst; Green reaction; Piperizine.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology
  • Catalysis
  • Escherichia coli / drug effects
  • Gas Chromatography-Mass Spectrometry
  • Green Chemistry Technology / methods
  • Models, Chemical
  • Nitriles / chemical synthesis*
  • Nitriles / pharmacology
  • Piperazine / chemistry*
  • Pyrans / chemical synthesis*
  • Pyrans / pharmacology
  • Staphylococcus aureus / drug effects
  • Water / chemistry

Substances

  • Anti-Bacterial Agents
  • Nitriles
  • Pyrans
  • Water
  • Piperazine