Method for preparing benzodinitrogen compound by using gold complex

Abstract

The invention relates to a method for preparing a benzodinitrogen compound by using a gold complex, which comprises the following step of: reacting an o-phenylenediamine compound and alkyne as raw materials with a gold complex containing a diphosphine ortho-carborane ligand as a catalyst at room temperature to obtain the benzodinitrogen compound. Compared with the prior art, the method has the advantages that the gold complex containing the diphosphine ortho-carborane ligand is used as the catalyst to efficiently catalyze the reaction of the o-phenylenediamine compound and the alkyne to synthesize the benzodinitrogen compound, the dosage of the catalyst is low (about 1.0 mol%), the selectivity is good, the reaction condition is mild, the reaction can be carried out at room temperature, additives are not needed, the reaction rate is high, the yield is relatively high, the substrate range is wide, and the method has a wide application prospect in industry.

Description

technical field [0001] The present invention belongs to benzodiazepine The technical field of compound preparation relates to a method for preparing benzodiazepines by using gold complexes method of compounds. Background technique [0002] Benzodiazepine Plasma compounds are an important class of heterocyclic compounds with pharmacological activity. They have functions such as sedative, hypnotic, anti-inflammatory, and anti-neurotic properties. They not only have potential pharmacological activities, but also serve as important synthetic intermediates for some fused ring compounds body. Therefore, the study of simple and efficient benzodiazepine The synthetic method of the compound is of great significance. [0003] The traditional synthesis method is mainly prepared by condensation reaction of o-phenylenediamine and α, β-unsaturated ketone, β-halogenated ketone or ketone compound (Tetrahedron Lett.2008, 49, 5302; Chem.Eur.J. 2009, 15, 8834). However, such condens...

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Problems solved by technology

This approach enables a more atom-economical synthesis, but uses a highly toxic mercury-containing catalyst

Liu in 2012 and Luo in 2014 reported the use of gold catalysts to replace mercury catalysts (J.Org.Chem.2012,77,4484; J.Organomet.Chem.2014,751,438), realizing the synthesis of o-phenylenediamine and Direct synthesis of benzodiazepines from alkynes However, they all require a higher reaction temperature, and the gold catalyst is easily deactivated at this temperature, which affects the catalytic efficiency.

In 2020, Liu et al. also reported a gold catalyst with catalytic activity at room temperature, but the catalyst was used in a large amount and had poor stability in the air, requiring higher reaction conditions (Chin.J.Org.Chem.2020 ,40,2520)

[0004] In summary, the synthesis of benzodiazepine Although the methods of compound-like compounds have been reported, each has its defects, such as unstable catalyst, high catalyst equivalent, additives required for reaction, long reaction time, high reaction temperature, etc., which limit its application.

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