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Method for catalytically synthesizing 1,4-dihydropyridine derivative through cooperation of zirconocene dichloride and benzoic acid ligands
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A technology of zirconocene dichloride and benzoic acid, applied in the direction of organic chemistry, etc., to achieve the effects of mild reaction conditions, wide biological activity and medicinal value, and simple operation
Pending Publication Date: 2019-07-12
SHAANXI NORMAL UNIV
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[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of the existing preparation methods of 1,4-dihydropyridine compounds, and to provide a method with mild conditions, simple operation, short reaction time, single reaction product, good substrate applicability, and high efficiency. Method for preparing 1,4-dihydropyridine compounds
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Embodiment 1
[0017] Preparation of ethyl 1-benzyl-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate of formula
[0018]
[0019] Into a 20mL reaction flask, add 0.2238g (1mmol) (Z)-3-(benzylamino)but-2-enoic acid ethyl ester, 146 μL (1.2mmol) cinnamaldehyde, 0.0125g (0.05mmol) dichlorodimethylene Zirconium, 0.0181g (0.1mmol) 5-nitrosalicylic acid, 3mL chloroform, stirred at 50 ° C for 2 hours, stopped the reaction, naturally lowered to room temperature, removed chloroform by rotary evaporation, and separated with a silica gel column ( The eluent is a mixture of ethyl acetate and petroleumether in a volume ratio of 1:10) to obtain 1-benzyl-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylic acidEthyl ester, the yield was 96%, and the characterization data were: 1 H NMR (600MHz, CDCl 3 )δ7.35(t,J=7.5Hz,2H),7.27(dd,J=14.7,5.9Hz,5H),7.22(d,J=7.4Hz,2H),7.17-7.13(m,1H), 5.95(d, J=7.6Hz, 1H), 4.97(dd, J=7.6, 5.5Hz, 1H), 4.68-4.54(m, 3H), 3.97(q, J=7.1Hz, 2H), 2.41(s , 3H), 1.08(t, J=7.1...
Embodiment 2
[0021] In this example, equimolar 3-nitrophthalic acid was used to replace 5-nitrosalicylic acid in Example 1, and other steps were the same as in Example 1 to obtain 1-benzyl-2-methyl-4 - ethyl phenyl-1,4-dihydropyridine-3-carboxylate in 84% yield.
Embodiment 3
[0023] In this example, equimolar 4-nitrophthalic acid was used to replace 5-nitrosalicylic acid in Example 1, and other steps were the same as in Example 1 to obtain 1-benzyl-2-methyl-4 - ethyl phenyl-1,4-dihydropyridine-3-carboxylate in 90% yield.
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Abstract
The invention discloses a method for catalytically synthesizing a 1,4-dihydropyridine derivative through cooperation of zirconocene dichloride and benzoic acid ligands. According to the method, with the zirconocene dichloride as a catalyst and 3-nitrophthalic acid, 4-nitrophthalic acid, 5-methoxysalicylic acid, 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid and the like as the ligands, intermolecular ring closure is performed between enamine ester and cinnamaldehyde to produce the 1,4-dihydropyridine derivative. By the method, a reaction condition is mild, the operation is simple, the reaction time is short, a reaction product is single, the atomic economy is high, and after the reaction, the 1,4-dihydropyridine derivative with wide biological activity and a high medicinal value can be obtained at a relatively high yield only through simple column chromatographic separation of the product.
Description
technical field [0001] The invention belongs to the technical field of 1,4-dihydropyridine synthesis, in particular to a method for catalyzing synthesis of 1,4-dihydropyridine derivatives by zirconocene dichloride and benzoic acid ligands. Background technique [0002] Derivatives of 1,4-dihydropyridines (1,4-DHPs) are rich in pharmacological and biological properties, widely present in natural products, and in addition, they are useful and versatile synthetic intermediates in organic chemistry. Therefore, the synthesis of 1,4-dihydropyridine derivatives has been extensively studied. The most famous method for the preparation of symmetrical 1,4-dihydropyridine is the classical Hantzch synthesis method: two molecules of β-carbonyl ester, one molecule of aldehyde and one molecule of ammonia undergo a condensation reaction to obtain dihydropyridine derivatives. Although the Hantzsch reaction is very useful in the synthesis of dihydropyridines, N-aryl-1,4-dihydropyridines and C...
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