Method for synthesizing 3,6-dihydropyran derivative
The technology of a dihydropyran derivative and a synthesis method is applied in the field of synthesis of dihydropyran derivatives, can solve the problems of many side reactions, difficult to obtain, difficult to control, etc., achieves high utilization rate of raw materials, and avoids the use of catalysts , The effect of reducing the side reaction of olefin polymerization
Active Publication Date: 2018-10-02
YUANJIANG HUALONG CATALYST TECH
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Problems solved by technology
Chinese patent (CN101143860A) discloses the synthesis of 5,6-dihydro-pyran and its derivatives through the Diels-Alder reaction of conjugated dienes and anhydrous formaldehyde under the catalysis of Lewis acid, due to Diels-Alder Both German and German reactions need to use Lewis acid as a catalyst, and need to be carried out at high temperature, and Lewis acid can also initiate olefin polymerization at the same time, resulting in many side reactions and difficult to control
Chinese patent (CN101481369A) discloses a method for efficiently synthesizing 4,6-position substituted 3,-4-dihydro-pyran-2-one derivatives from aldehyde group-substituted cyclopropane compounds using azacyclic carbene as a catalyst , the aldehyde group-substituted cyclopropane compound used in this method is a kind of raw material that is difficult to obtain, and the cost is relatively high
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[0036] The following examples are intended to further illustrate the content of the present invention, rather than limit the protection scope of the claims of the present invention.
[0037] All reactions were performed in Schlenk tubes unless otherwise stated.
[0038]All reaction stock solvents were obtained from commercial sources and used without further purification.
[0039] Product separation adopts silica gel chromatographic column, silica gel (particle size 300 mesh-400 mesh).
[0040] 1H NMR (400MHz), 13C NMR (100MHz) and 19F NMR (376MHz) detection adopts Bruker ADVANCEIII spectrometer, with CDCl 3 As the solvent, TMS is used as the internal standard, the chemical shift is in parts per million (ppm), and 0.0 ppm of tetramethylsilane is used as the reference shift. The following abbreviations (or combinations thereof) are used to explain multiplicity: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broad. The unit of the coupling constant J ...
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Abstract
The invention discloses a method for synthesizing a 3,6-dihydropyran derivative. The method is characterized in that aryl aldehyde and 2-aryl propylene are subjected to one-pot reaction in a dimethylsulfoxide solution system containing potassium persulfate, and the dihydropyran derivative is obtained. According to the method, a 3,6-dihydropyran ring is formed by carbonyl provided by aryl aldehyde, propenyl provided by 2-aryl propylene and methyl provided by dimethyl sulfoxide together for the first time. The synthesis method is implemented with a one-pot process, adopts mild reaction conditions, is good in selectivity and high in yield, requires no additional catalysts, and is beneficial to industrial production.
Description
technical field [0001] The present invention relates to a method for synthesizing dihydropyran derivatives, in particular to a method for jointly constructing 3,6-dihydropyran by aryl aldehyde, 2-aryl propene and dimethyl sulfoxide through a one-pot method The method belongs to the field of organic intermediate synthesis. Background technique [0002] Dihydropyran derivatives are an important class of six-membered oxygen-containing heterocyclic compounds with unique biological and pharmaceutical activities. For example, Zanamivir is an anti-influenza virus drug, and Benesudon can be used as an antibiotic. It is also an important Organic intermediates such as 2-ethoxy-3,4-dihydropyran are relatively inexpensive synthetic glutaraldehyde intermediates, which can be hydrolyzed to obtain glutaraldehyde. Therefore, dihydropyran derivatives have attracted the attention of many organic chemists and pharmacologists, and they are also one of the most studied heterocyclic compounds in...
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Patent Timeline
Login to View More IPC IPC(8): C07D309/18C07D309/22C07D309/20C07D409/04
CPCC07D309/18C07D309/20C07D309/22C07D409/04
Inventor 郭灿城李慧郭欣
Owner YUANJIANG HUALONG CATALYST TECH