129196-82-3Relevant academic research and scientific papers
Diastereoselective Diels-Alder Reaction of 2-Thienyl and 2-Furyl Substituted 3-Propenethioamides with Electron Deficient Dienophiles
Bogdanowicz-Szwed, Krystyna,Budzowski, Artur
, p. 97 - 108 (2004)
The hetero-Diels-Alder reaction of N-aryl-3-(2-thienyl)-2- propenethioamides with N-phenylmaleimide and maleimide yielded a mixture of endo- and exo-2-arylimino-4-(2-thienyl)tetrahydrothiopyran[2,3-c]pyrroles. Cycloaddition to diethyl fumarate required acylation and furnished a mixture of diastereoisomeric 5-(N-acetylphenylamino)-2,3-bis-(ethoxycarbonyl)-4-(2-thienyl) -3,4-dihydro-2H-thiopyrans. Reactions of 3-(2-furyl)-2-propenethioamides with N-arylmaleimides furnished the correspondent 2-arylimino-4-(2-furyl) tetrahydrothiopyran[2,3-c]pyrroles. In the cycloadditions of the heterodienes with N-arylmaleimides the endo-cycloadducts were formed as the major products.
Manganese(I) Catalyzed α-Alkenylation of Amides Using Alcohols with Liberation of Hydrogen and Water
Pandia, Biplab Keshari,Gunanathan, Chidambaram
, p. 9994 - 10005 (2021/07/31)
Herein, unprecedented manganese-catalyzed direct α-alkenylation of amides using alcohols is reported. Aryl amides are reacted with diverse primary alcohols, which provided the α,β-unsaturated amides in moderate to good yields with excellent selectivity. Mechanistic studies indicate that Mn(I) catalyst oxidizes the alcohols to their corresponding aldehydes and also plays an important role in efficient C═C bond formation through aldol condensation. This selective olefination is facilitated by metal-ligand cooperation by the aromatization-dearomatization process operating in the catalytic system. Biorenewable alcohols are used as alkenylation reagents for the challenging α-alkenylation of amides with the highly abundant base metal manganese as a catalyst, which results in water and dihydrogen as the only byproduct, making this catalytic transformation attractive, sustainable, and environmentally benign.
Nickel(0) induzierte und katalysierte CC-Verknuepfungen zwischen Phenylisocyanat und vinylsubstituierten Heteroaromaten
Hoberg, Heinz,Guhl, Dieter,Betz, Peter
, p. 233 - 246 (2007/10/02)
Vinyl substituted heterocycles such as 2-vinylfuran (Ia) and 2-vinylpyridine (Ib) react with phenylisocyanate (II) in presence of (Lig)Ni0 (Lig = TCP) to form the tricyclohexylphosphane-5-azanickelacyclopentan-4-one derivatives (V).The structures and properties of these metallacycles are described.A catalytic 1/1 CC bond formation to give the α,β-unsaturated carboxylic acid amide X proceeds only with Ia (Lig = P(OiP)3) and not with Ib (Lig = PEt3, PPh3, P(OiP)3).Presumably, the different reactivities are not caused by electronic and/or steric factors of the 2-furyl- or 2-pyridyl-substituents, but by the donor properties of the N-atom in Ib.The N Ni interactions in the complex bis2-2-vinyl-μ-pyridine-nickel> (XIIb) can be detected by spectroscopic and crystal structure studies.
