13304-62-6Relevant articles and documents
Solid-phase synthesis of 2-alkenamides from polystyrene-supported α-selenocarboxylic acids
Liu, Xiao-Ling,Wang, Xing-Cong,Sheng, Shou-Ri
, p. 1303 - 1306 (2004)
The polystyrene-supported α-selenoacetic acid and α-selenopropionic acid were prepared and used for the synthesis of 2-alkenamides from primary and secondary amines in good yields and high purities.
Ionic Liquid as a Suitable Phase for Multistep Parallel Synthesis of an Array of Isoxazolines
Rodriquez, Manuela,Sega, Alessandro,Taddei, Maurizio
, p. 4029 - 4031 (2003)
(Equation presented) A parallel array of isoxazoline diamides was prepared using an ionic liquid [bmim][BF4] as the phase where a three-step procedure (Schotten-Baumann, 1,3-dipolar cycloaddition, ester amidation with Me3Al) was carr
The phosphazo route to 2-alkenamides from acrylic acid and its derivatives
Cabral, Jose,Laszlo, Pierre,Montaufier, Marie-Therese,Lalatiana Randriamahefa
, p. 1705 - 1708 (1990)
2-Alkenamides are formed in good isolated yields (generally up to 70%) by the reaction of in situ-generated phosphazo compounds issued from aliphatic, alicyclic and aromatic primary amines, with acrylic acid and its derivatives.
Direct Photoredox-Catalyzed Reductive Difluoromethylation of Electron-Deficient Alkenes
Tang, Xiao-Jun,Zhang, Zuxiao,Dolbier, William R.
, p. 18961 - 18965 (2015)
Photoredox-catalyzed reductive difluoromethylation of electron-deficient alkenes was achieved in one step under tin-free, mild and neutral conditions. This protocol affords a facile method to introduce RCF2 (R=H, Ph, Me, and CH2N3) groups at sites β to electron-withdrawing groups. It was found that TTMS (tris(trimethylsilyl)silane) served nicely as both the H-atom donor and the electron donor in the catalytic cycle. Experimental and DFT computational results provided evidence that RCF2 (R=H, Ph, Me) radicals are nucleophilic in nature.
Retro-aza-Michael reaction of an o-aminophenol adduct in protic solvents inspired by natural products
Kakeya, Hideaki,Kaneko, Kensuke,Nishimura, Shinichi,Takahashi, Nobuaki,Takenaka, Kei
, (2021)
α,β-Unsaturated carbonyls are reactive group often found in bioactive small molecules. Their non-specific reaction with biomolecules can be the cause of the low efficacy and unexpected side-effects of the molecule. Accordingly, unprotected α,β-unsaturated carbonyls are not often found in drugs. Here, we report that o-aminophenol is a new masking group of α,β-unsaturated ketone, which is inspired by natural products saccharothriolides. o-Aminophenol adduct of α,β-unsaturated ketone, but not those of α,β-unsaturated amide or ester, undergoes a retro-Michael reaction to yield o-aminophenol and the Michael acceptor. This reaction was observed only in protic solvents, such as MeOH and aqueous MeOH. In contrast, o-anisidine was not eliminated from its Michael adduct. o-Aminophenol may be a promising masking tool of highly-reactive bioactive α,β-unsaturated carbonyl compounds.
Rhodium(III)-Catalyzed Synthesis of Skipped Enynes via C(sp3)–H Alkynylation of Terminal Alkenes
Della-Felice, Franco,Zanini, Margherita,Jie, Xiaoming,Tan, Eric,Echavarren, Antonio M.
supporting information, p. 5693 - 5698 (2021/02/09)
The RhIII-catalyzed allylic C?H alkynylation of non-activated terminal alkenes leads selectively to linear 1,4-enynes at room-temperature. The catalytic system tolerates a wide range of functional groups without competing functionalization at other positions. Similarly, the vinylic C?H alkynylation of α,β- and β,γ- unsaturated amides gives conjugated Z-1,3-enynes and E-enediynes.
Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions
Ahmar, Mohammed,Queneau, Yves,Verrier, Charlie,Yue, Xiaoyang
, p. 319 - 330 (2021/10/29)
The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.
