92444-70-7Relevant articles and documents
Method for preparing N-vinyl amide compound under catalysis of copper salt
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Paragraph 0050-0051, (2020/06/09)
The invention discloses a method for preparing an N-vinyl amide compound under the catalysis of a copper salt. The method comprises the following steps: reacting amide and vinyl alkyl ether in a closed container at 95-105 DEG C for 4-10 hours under the protection of inert gas in the presence of a copper salt catalyst and an organic solvent; and after the reaction is finished, cooling reaction liquid to room temperature, and carrying out separating and purifying to obtain the N-vinyl amide compound, wherein the copper salt catalyst is anhydrous cupric sulfate or a complex of anhydrous cupric sulfate and 8-hydroxyquinoline in a mass ratio of (2-1): 1, and a molar ratio of the amide to the vinyl alkyl ether to the copper salt catalyst is 20: (100-200): (2-1). According to the method, the simple copper salt is used as the catalyst; and compared with conventional methods, the method has the advantages that the catalyst is cheap and easy to obtain, no halogen is introduced in the reactions,the method is environmentally friendly, additives such as acid and alkali do not need to be added in the reaction, and a system is simple. The invention provides the method for effectively preparing the N-vinyl amide compound.
Axially Chiral Enamides: Substituent Effects, Rotation Barriers, and Implications for their Cyclization Reactions
Clark, Andrew J.,Curran, Dennis P.,Fox, David J.,Ghelfi, Franco,Guy, Collette S.,Hay, Benjamin,James, Natalie,Phillips, Jessica M.,Roncaglia, Fabrizio,Sellars, Philip B.,Wilson, Paul,Zhang, Hanmo
, p. 5547 - 5565 (2016/07/14)
The barrier to rotation around the N-alkenyl bond of 38 N-alkenyl-N-alkylacetamide derivatives was measured (ΔG∞ rotation varied between -1). The most important factor in controlling the rate of rotation was the level of alkene substitution, followed by the size of the nitrogen substituent and, finally, the size of the acyl substituent. Tertiary enamides with four alkenyl substituents exhibited half-lives for rotation between 5.5 days and 99 years at 298 K, sufficient to isolate enantiomerically enriched atropisomers. The radical cyclizations of a subset of N-alkenyl-N-benzyl-α-haloacetamides exhibiting relatively high barriers to rotation round the N-alkenyl bond (ΔG∞ rotation >20 kcal mol-1) were studied to determine the regiochemistry of cyclization. Those with high barriers (>27 kcal mol-1) did not lead to cyclization, but those with lower values produced highly functionalized γ-lactams via a 5-endo-trig radical-polar crossover process that was terminated by reduction, an unusual cyclopropanation sequence, or trapping with H2O, depending upon the reaction conditions. Because elevated temperatures were necessary for cyclization, this precluded study of the asymmetric transfer in the reaction of individual atropisomers. However, enantiomerically enriched atropsiomeric enamides should be regarded as potential asymmetric building blocks for reactions that can be accomplished at room temperature.
NEW SYNTHESIS OF SECONDARY CARBOXAMIDE BY USING 2-METHYL-2-OXAZILONE AS A BUILDING BLOCK
Inaba, Masami,Moriwake, Toshio,Saito, Seiki
, p. 3235 - 3238 (2007/10/02)
New method for the synthesis of secondary carboxamides of type, R2NHCOR1, which utilizes 2-methyl-2-oxazoline as a carboxamide building block and various halides, R2X, has been developed.
A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 12. A General Synthesis of 2-Chloropyridines and 2-Pyridons
Meth-Cohn, Otto,Westwood, Keith T.
, p. 1173 - 1182 (2007/10/02)
The Vilsmeier formylation of tertiary and secondary enamides leads to 2-pyridons and 2-chloropyridines, respectively.The reaction appears to be quite general allowing substitution in the 1-, 3-, 5-, or 6-position or combinations of these.The major limitation arises with enamides which are unsymmetrically substituted on the double bond with alkyl groups, when mixtures can result.Attempts to introduce a 4-substituent by a variation of the Vilsmeier reagent had limited success.
