Copper-Mediated C−N Bond Formation via Direct Aminolysis of Dithioacetals

Abstract

Mediated by copper acetate, an efficient approach to the C-N bond formation via direct aminolysis of dithioacetals 2 and 5 with ammonia, primary or secondary amines are developed under mild conditions. Enaminones 3 and 6 were thus obtained in high to excellent yields with high chemoselectivity. This type of aminolysis reaction presents a new synthetic application of the dithioacetal functionality. [reaction: see text]

Design of a graphene oxide-SnO2 nanocomposite with superior catalytic efficiency for the synthesis of β-enaminones and β-enaminoesters

“…These chemicals are a highly multifaceted class of intermediates for the synthesis of heterocyclic and biologically active compounds. The conventional synthesis protocols used for benaminones and b-enaminoesters involved condensation of carbonyl compounds with amines catalyzed by chlorides, 17,18 metal oxides, 19 aurates, 20 SiO 2 and it's composite, 16,[21][22][23] ionic liquids, 24 and triates. In particular, the enaminones and enaminoester moieties have attracted much interest, because they are fundamental and versatile starting materials for the synthesis of heterocycles, 3 alkaloids, 4,5 g-amino alcohol, 6 quinolines, 7 azocompounds 8 and a,b-amino acids.…”

Fabrication of Nano‐CuO@ZnO for the Synthesis of Functionalized β‐Enaminone Derivatives from β‐Nitrostyrenes, Aliphatic/Aromatic Amines and 1,3‐Dicarbonyl/4‐Hydroxy Coumarin

“…The condensation of active methylene compounds and ketones in presence of dimethoxy‐ N,N ‐dimethylmethanamine was also adopted to prepare these moieties . Later on, β ‐enaminones were synthesized via copper‐catalyzed aminolysis of β ‐carbonyl 1,3‐dithianes with amines and by the reaction of 1,3‐dicarbonyls with amines …”

Zeolite (ZSM‐5) as a Highly Efficient and Heterogeneous Catalyst for the Synthesis of β‐Enaminones and β‐Enamino Esters

“…Sc(OTf) 3 25 and Yb(OTf) 3 26 . Some other routes to the synthesis of β-Enaminones include condensation of methyl ketones with dimethylformamide dimethylacetals 27 , aminolysis of dithioacetals mediated by copper acetate 28 , reductive cleavage of isoxazoles 29 , cyclization of aminoacids 30 and substitution of the imidoylbenzotriazoles with trimethylsilyl enol ethers 31 . Out of these methods, most of them suffer from various disadvantages such as long reaction time and unspecified yields, use of expensive reagents, tedious work-up and lack of general applicability etc.…”