Preparation method of alpha, beta-unsaturated amide compound
An amide compound, unsaturated technology, applied in the field of preparation of α, β-unsaturated amide compounds, to achieve the effect of easy operation, simple preparation method and wide tolerance range
Active Publication Date: 2022-01-07
ZHEJIANG SCI-TECH UNIV
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Problems solved by technology
However, to the best of our knowledge, the aminocarbonylation of alkenyl triflates with nitroarenes to α,β-unsaturated amides under the catalytic system of nickel and carbon monoxide substitutes has not been reported.
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Embodiment 1～15
[0032] Add 1,2-bis(biphenylphosphineethane)nickel chloride, 4,4'-di-tert-butyl-2,2'-bipyridine, molybdenum carbonyl , potassium phosphate, water, alkenyl triflate (II) and nitroarenes (III), then add 1,4-dioxane (2mL), mix and stir evenly, and react according to the reaction conditions in Table 2 , after the reaction is completed, filter, mix the sample with silica gel, and obtain the corresponding α,β-unsaturated amide compound (I) through column chromatography purification, the reaction process is shown in the following formula:
[0033]
[0034] The raw material addition of table 1 embodiment 1~15
[0035]
[0036] Table 2
[0037]
[0038] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, OMe is a methoxy group, Me is a methyl group, Et is an ethyl group, OPh is a phenoxy group, CF 3 is trifluoromethyl, Ph is phenyl.
[0039] The structural confirmation data of the compounds prepared in Examples 1-5:
[0040] The nuclear magnetic r...
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The invention discloses a preparation method of an alpha, beta-unsaturated amide compound. The method comprises the following steps of: making 1, 2-bis (biphenylphosphine ethane) nickel chloride, 4, 4 '-di-tert-butyl-2, 2'-dipyridyl, carbonyl molybdenum, potassium phosphate, water, alkenyl trifluoromethanesulfonate and nitro-aromatic hydrocarbon react at 110 DEG C for 36 hours, and after the reaction is completed, performing post-treatment to obtain the alpha, beta-unsaturated amide compound. The preparation method takes nitro-aromatic hydrocarbon as a nitrogen source and carbonyl molybdenum as both a carbonyl source and a reducing agent, and is simple to operate, cheap and easily available in reaction starting raw materials, wide in tolerance range of substrate functional groups and high in reaction efficiency. Various alpha, beta-unsaturated amide compounds can be synthesized according to actual needs, and the practicability of the method is widened while the operation is convenient.
Description
technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of α,β-unsaturated amide compounds. Background technique [0002] α,β-Unsaturated amide compounds are a class of valuable molecules, which usually exist as important backbone molecules in various natural products, biomolecules and drugs (Nature 2009, 38, 606-631). They can also play a very important role as synthetic intermediates in organic transformations (Chem. Rev. 2002, 102, 3067-3083.). The traditional method for synthesizing α,β-unsaturated amides is to obtain them through the nucleophilic substitution reaction of α,β-unsaturated carboxylic acids and amines in the presence of coupling agents. In addition, transition metal-catalyzed carbonylation reactions also provide a convenient and fast method for the synthesis of α,β-unsaturated amides. However, in such carbonylation reactions, expensive transition metal catalysts and highly toxic carbon monoxide...
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IPC IPC(8): C07C231/10C07C233/58C07C233/60C07C233/62
CPCC07C231/10C07C2601/10C07C2601/16C07C2601/18C07C233/58C07C233/60C07C233/62Y02P20/584
Inventor 祁昕欣霍永旺吴小锋
Owner ZHEJIANG SCI-TECH UNIV