Choline chloride‐urea deep eutectic solvent as an efficient media for the synthesis of propargylamines via organocuprate intermediate

Abstract

A facile method for the synthesis of various propargylamines derivatives with different structural parts has been reported. The reaction has consisted of onepot coupling between aldehydes, secondary amines and terminal alkynes using CuCl as a catalyst and choline chloride/urea DES as a cheap and biocompatible reaction media. The procedure is free of using toxic solvents and used CuCl as an available, inexpensive and non-toxic catalyst. Using this methodology, 15 different propargylamine derivatives were successfully synthesized at 60 C in 15 hr, mostly in good yields.

Synthesis, characterization, and reactivity of a novel magnetically recyclable triazine‐based Cu–NNN–pincer complex

“…Due to the importance of propargylamines, various metal complexes and salts have been used to achieve this reaction under homogeneous or heterogeneous conditions. [20,27,[62][63][64][65][66][67][68] In continuation of our previous research on the development of functionalized nanocatalysts and their applications in various organic transformations, [69][70][71] herein, we report a novel heterogeneous and recyclable triazine-based Cu-NNN-pincer complex, Fe 3 O 4 @SiO 2 -NH-CCl-AT-Cu(II), as a novel, nontoxic, and low-cost catalyst for the preparation of propargylamines from A 3 coupling reactions of aldehydes, phenylacetylene, and amines.…”

“…Due to the importance of propargylamines, various metal complexes and salts have been used to achieve this reaction under homogeneous or heterogeneous conditions. [ 20,27,62–68 ]…”

Choline Chloride-Based DES as Solvents/Catalysts/Chemical Donors in Pharmaceutical Synthesis

“…Because of its versatility and wide use in organic synthesis, a number of methodologies have been developed for propargylamine derivatives, in particular three-component reactions of aldehydes, amines, and alkynes [ 53 ]. This method has been recently improved by substituting the classical solvents with environmentally friendly ChCl/urea [ 54 ]. First, the reaction between benzaldehyde, morpholine, and phenylacetylene in the presence of CuCl (5 mol%) as a catalyst was selected as a model to set the best conditions (solvent, catalyst amount, temperature, and time).…”

CuI‐catalyzed, one‐pot synthesis of 3‐aminobenzofurans in deep eutectic solvents

“…[26,27] Instead, their new generation, named as deep eutectic solvents (DESs), [28] solved the most of these problems, in addition to covering the common benefits of ILs. [29] Following the previous works of this group to develop the synthetic methodologies by using DESs [30][31][32][33] and a recent report on preparation of benzofuran derivatives, [34] the preparation of benzofuran derivatives has been considered under green media condition in this study.…”