Study On Organic Reactions Involving Phenylboronic Acid And Amino Compounds

Phenylboronic acid and amino compounds are very important substances in organic synthesis and they can participate in many different types of chemical reactions.The organic reactions in which the two participate together have infinite possibilities in synthetic chemistry and medicinal chemistry,and it is very valuable to further study these reactions.Our research group is not only committed to the optimization of reaction methods and innovation of reaction catalyst,but also follows the concept of green and sustainable development in scientific research.Most of the reactions reported in the previous literatures have not met the requirements of green and sustainable chemistry.There are many problems such as too high reaction temperature,unsatisfactory reaction yield,and environmental pollution caused by reaction reagents.I applied this idea to each step of the experiment in the research process of organic reactions involving phenylboronic acid and amino compounds.In this paper,phenylboronic acid and some special amino-containing compounds are used as raw materials to participate in different types of reactions to synthesize 1,3,2-benzodiazaborininones,alkylaminophenols,and pyrido[1,2-a]benzimidazoles.Boron nitrogen heterocyclic compounds containing B-N bonds have shown great application value in materials chemistry and biomedical research.In this paper,Pd/Ni catalyst was successfully used to synthesize 1,3,2-benzodiazaborininones from phenylboronic acid and anthranilamide under mild conditions.This mild reaction condition has high efficiency in large-scale reactions,and the synthesis method can synthesize a variety of substrates,which is suitable for various aromatic,heteroaromatic,alkenyl and alkylboronic acids,and the synthesis method greatly reduces the reaction time,and the yield is high.The “one-pot method” of some multicomponent reactions has the advantages of mild reaction conditions,simple operation process,and good functional group compatibility.It has been widely used in the design of medicine,the synthesis of organic compounds,and the preparation of biologically active molecules."One-pot method" Petasis reaction is an important means of synthesizing some natural products and drugs.In this paper,a greener solvent,cyclopentyl methyl ether,was found to replace the previously toxic 1,2-dichloroethane and 1,4-dioxane,making the reaction consistent with modern chemical concepts.We have not only proved that cyclopentyl methyl ether has good adaptability during the reaction,but also verified that the steric hindrance of cyclic lactams containing benzene rings is obvious when participating in Petasis reaction with phenylboronic acid and salicylaldehyde.Pyrido[1,2-a]benzimidazoles are nitrogen-containing heterocyclic compounds with a tricyclic ring system,which have great potential in pharmaceutical synthesis.In this paper,a series of pyrido[1,2-a]benzimidazole derivatives were successfully obtained by one-step reaction of phenylboronic acid and o-aminopyridine.Compared with the previous method,not only the reaction time is reduced,but also the reaction yield is improved.