Novel method for preparing phosphoryl azo compounds

Abstract

The invention provides a method for preparing phosphoryl azo compounds with high efficiency and high selectivity; pyridine is used as alkali, an aryl diazonium tetrafluoroborate compound and a P(O)-Hcompound are used as reaction substrates, and an organic solvent is added into a reaction system. The method has the advantages that a catalyst is cheap and easily available; the substrate applicability is high; reaction conditions are mild, safe and reliable; the selectivity of the obtained target products is close to 100%, and the yield is high. The method overcomes the defects of harsh reactionconditions, poor reaction selectivity, complex experimental steps, low yield, need of reagents harmful to the environment and the like in a traditional synthesis of phosphoryl azo compounds, and hasfavorable industrial application prospects. The invention also provides the corresponding phosphoryl azo compounds containing different substituted functional groups.

Description

technical field [0001] The invention relates to the field of catalytic synthesis of phosphoryl azo compounds, in particular to a method for efficiently preparing phosphoryl azo compounds and The preparation method of its derivatives. Background technique [0002] Phosphoryl azo compounds are important intermediates in organic synthesis. They are widely used in the preparation of organic dyes, natural product pharmaceutical structure substances, polymer intermediates, extractants, photoelectric materials, flame retardants, food additives, and pesticides. Phosphoramides are one of the earliest and most basic chemical substances found in nature. They constitute the basic skeleton of important living organisms and exist in many natural products and pharmaceuticals. [0003] Using aniline compounds, phosphorus oxyhalide compounds (fluorine, chlorine, bromine, etc.), alkyl nitrites and hydrochloric acid can directly realize the cross-coupling reaction at low temperature. This me...

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Problems solved by technology

[0003] Using aniline compounds, phosphorus oxyhalide compounds (fluorine, chlorine, bromine, etc.), alkyl nitrites and hydrochloric acid can directly realize the cross-coupling reaction at low temperature. This method can avoid many defects caused by the use of activating reagents. It is an ideal way to synthesize phosphoryl azo compounds, but the reaction temperature needs to be strictly controlled in the process, the reaction requires vigorous stirring and a special reactor, and the requirements for the substrate are high, and there cannot be the presence of highly active functional groups. And above-mentioned method generally all adopts air-sensitive reagent, and there are also cumbersome experimental steps, low atom economy, difficult separation, and accompanying by-products pollute the environment

[0004] So far, the efficient synthesis of phosphoryl azo compounds with special functional skeletons has several problems, such as raw material quality, production safety (phosphoryl halides, hydrochloric acid and other compounds are highly corrosive), and product stability and purity. There are two problems, and the synthesis technology is quite difficult. At present, only a few companies in the United States, Germany, Japan and other countries are producing, and the current situation of my country's high-end phosphoryl azo compounds and other products mainly depends on imports.