Solvent-free synthesis of propargylamines: an overview

Abstract

This review focuses on solvent-free methodologies for the synthesis of propargylamines, a versatile class of compounds with numerous applications.

Metal–organic framework (MOF)-, covalent-organic framework (COF)-, and porous-organic polymers (POP)-catalyzed selective C–H bond activation and functionalization reactions

“…Propargylamines are a key class of compounds in organic chemistry with a wide range of pharmaceutical and biological activities. 389,390 One of the direct methods for the synthesis of propargylamines is the threecomponent coupling of aldehydes, amines, and terminal alkynes (A 3 coupling reaction). When a ketone is used instead of an aldehyde, the reaction is called KA 2 coupling.…”

“…391 These approaches involve metal-catalyzed C-C bond formation via the C-H activation of terminal alkynes. 49,389,390 Phan et al 70 70 It should be noted that the reaction required TBHP as an organic oxidant.…”

“…391 These approaches involve metal-catalyzed C–C bond formation via the C–H activation of terminal alkynes. 49,389,390 Phan et al 70 synthesized a variety of N -methyl- N -(3-phenylprop-2-ynyl)benzenamines via the MOF-199-catalyzed direct oxidative C(sp 3 )–C(sp) coupling reaction between N , N -dimethylaniline and terminal alkynes. MOF-199 is a copper-based MOF, also called HKUST-1 (HKUST = Hong Kong University of Science and Technology) or Cu-BTC or Cu 3 (BTC) 2 (BTC = 1,3,5-benzenetricarboxylate).…”

Gold nanoparticle decorated dithiocarbamate modified natural boehmite as a catalyst for the synthesis of biologically essential propargylamines

“…Aer optimizing the condition of the model reaction (0.1 mol% of gold NPs onto the g-AlO(OH)@C-NHCS 2 H$Au NPs , Cs 2 CO 3 as the base and 60 C as reaction temperature), the generality of the catalyst toward the A 3 -coupling reaction has been tested in the presence of a variety of aldehydes, amines, and phenylacetylene. All the subsequent reactions have been Table 1 The study results on the effect of various solvents on the A 3 a Reaction conditions: 1.2 mmol of morpholine, 1 mmol of benzaldehyde, and 1.3 mmol of phenylacetylene. b Isolated yields.…”

A metal-free BF3·OEt2 mediated chemoselective protocol for the synthesis of propargylic cyclic imines

“…In spite of the fact that a plethora of reports are available for the synthesis of biologically active propargyl amines and propargyl imines, 5 there are very few methods in the literature for the synthesis of propargylic cyclic imines. Propargylic cyclic imines can be utilized as readily available precursors to synthesize propargylic cyclic amines.…”