Efficient Microwave‐Assisted Synthesis of Secondary Alkylpropargylamines by Using A³‐Coupling with Primary Aliphatic Amines

Thiol–Yne Coupling of Propargylamine under Solvent‐Free Conditions by Bond Anion Relay Chemistry: An Efficient Synthesis of Thiazolidin‐2‐ylideneamine

“…We started our investigation by treating propargylamine 1a (1.0 mmol) with phenyl isothiocyanate ( 2a ; 1.0 mmol), in the presence of Cu(OTf) 2 (20 mol‐%). This reaction gave a chromatographically separable mixture of 4a and 5a (Table , Entry 1).…”

Concise and Diversity‐Oriented Route toward Polysubstituted 2‐Aminoimidazole Alkaloids and Their Analogues

“…Next, we applied our protocol to the total synthesis of 1,4,5-trisubstituted 2-aminoimidazole alkaloids of the naamine family (Scheme 4). The starting N-methylpropargylamines 11 a-f were readily accessed through a microwaveassisted copper(I)-catalyzed A 3 -coupling reaction [11] followed Table 1: Synthesis of the protected 2-iminoimidazolines from secondary propargylamines. [12] Entry…”

Copper(I)‐Catalyzed Four‐Component Coupling Using Renewable Building Blocks of CO2 and Biomass‐Based Aldehydes

“…Previously, phenyl-substituted bis-oxazolidinone was prepared by copper-catalyzed four-component coupling between phenylacetylene, benzaldehyde, diamine hydrochloride salt, and CO 2 . [41,67,71,72] For path a, the Cu I species initially reacts with a terminal alkyne to give a terminal copper-acetylide intermediate 8, presumably with the help of amine. [42] In our case, in addition to the synthesis of furyl-containing bis-oxazolidinone products 5a and 5b, we further investigated the preparation of furyl-containing poly-oxazolidinone 7 by the CuI-coupling of 1,3-diethynylbenzene furfural, 1,6-hexanediamine, and CO 2 (Scheme 3).…”