Method for synthesizing beta-amidocarbonyl compounds

Abstract

The invention provides a method for synthesizing beta-amidocarbonyl compounds. The reaction general formula is disclosed in the specification, wherein R1, R2, R3 and R4 are respectively a substituent group; R1 can be H, F, Cl, Br, NO2, CH3, OCH3 or any other single group, and can also be 2,4-2Cl, 2-Cl-5-F or any other double-substituent group, and the quantity and position of the substituent groups are not defined; R2 can be H, and can also be NO2, CH3, OCH2CH3, aromatic group or any other substituent group; and R3 can be H, and can also be CH3, COOC2H5 or any other substituent group, or hexahydric cycloalkyl group formed by R2, R3 and carbon atom connected with R2 and R3. The reaction is carried out at room temperature in the presence of acetyl chloride by using titanium tetrachloride as a catalyst; and the purification adopts recrystallization, column chromatography or any other separation method. The invention has the advantages of accessible raw materials, simple technique, mild reaction conditions and cheap and nontoxic catalyst; and the applicable substrate range for reaction is wide, and thus, different substrates can be utilized to synthesize a series of beta-amidocarbonyl compounds.

Description

(1) Technical field [0001] The invention relates to a synthesis method for preparing β-acetamide carbonyl compounds (β-acetamide carbonyl compounds) through the reaction of aromatic aldehydes, carbonyl compounds and nitrile compounds. (2) Background technology [0002] In recent years, β-amide ketones have attracted the attention of chemists and medical scientists because their structures widely exist in many natural drug structures with physiological and pharmacological activities. β-amide carbonyl compounds can be easily converted into 1,3-diaminoalcohols, or β-amino acids and other compounds. Compounds such as 1,3-diaminoalcohol and β-amino acid are the core structures for the synthesis of some nucleoside peptide antibiotics, such as nikkomycin and neosporin. The precursor of β-aryl isotreonine can be combined with a molecule of amino acid to form the corresponding dipeptide isomer, and it can also be synthesized using β-amide carbonyl compound as a precursor. Mechanism...

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Problems solved by technology

[0009] (2) In 2011, the Bahulayan group in India used metal organic compounds Metalopthalocyanines as catalysts to synthesize such compounds in the presence of acid chlorides, but the catalysts used in this method are more toxic

[0011] (3) Momeni et al. used Zn(HSO 4 ) 2 and Co(HSO 4 ) 2 Such compounds were collectively weighed as catalysts at room temperature, but this method only involves CH 3 CN is used as a reactant and a solvent, and no other nitrile compounds are involved as a solvent, and the structure of the reaction substrate is relatively limited

[0013] (4) In 2007, Khan et al reported the use of FeCl 3 Catalyzing this type of reaction has obtained relatively good results, but the benzaldehyde with the -NO2 substituent involved in this type of method cannot obtain the corresponding expected product, and what is obtained is the product of the Brain Wenger reaction

[0016] In summary, in the known synthetic method of β-amide carbonyl compound, or temperature is higher, or catalyst is expensive, is difficult to prepare, or the scope of the applicable substrate of method is narrower

These deficiencies have brought a lot of inconvenience to the synthesis of this type of compound, especially industrialized production

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