Issue 14, 2019

A 3,4-dihalo-2(5H)-furanone initiated ring-opening reaction of DABCO in the absence of a metal catalyst and additive and its application in a one-pot two-step reaction

Abstract

In the absence of metal catalysis and an additive, with ethyl acetate as a solvent at 95 °C under air atmosphere for 2 h, an eco-friendly and practical protocol for the synthesis of 4-ethylpiperazine derivatives through a 3,4-dihalo-2(5H)-furanone initiated ring-opening reaction of DABCO is developed. Satisfactory reactivity with moderate to excellent yields and 100% atom economy are observed. This potential bioactive synthon promoted ring-opening reaction is not only important for the development of new drugs, but also suitable for other cyclic tertiary amines (e.g. 1-methylpyrrolidine) with good yields. In addition, due to the newly generated alkyl halide structural unit in the product, its application in one-pot two-step reactions with different kinds of nucleophilic reagents can be achieved as designed.

Graphical abstract: A 3,4-dihalo-2(5H)-furanone initiated ring-opening reaction of DABCO in the absence of a metal catalyst and additive and its application in a one-pot two-step reaction

Supplementary files

Article information

Article type
Communication
Submitted
25 May 2019
Accepted
17 Jun 2019
First published
18 Jun 2019

Green Chem., 2019,21, 3782-3788

A 3,4-dihalo-2(5H)-furanone initiated ring-opening reaction of DABCO in the absence of a metal catalyst and additive and its application in a one-pot two-step reaction

H. Wu, K. Yang, X. Chen, M. Arulkumar, N. Wang, S. Chen and Z. Wang, Green Chem., 2019, 21, 3782 DOI: 10.1039/C9GC01740B

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