A kind of amide compound and its preparation method and application

Abstract

The invention relates to the technical field of organic synthesis, in particular to an amide compound as well as a preparation method and application thereof. The preparation method for the amide compound comprises the following step of under the existence of an inert solvent and the function of a catalyst, enabling a compound in a formula (II) and a compound in a formula (III) to react, so as toobtain a compound in a formula (I). The preparation method has the advantages that the primer is simple and is easy to obtain, the additional directing group-assisted direct alkynylation reaction of hydrocarbon bonds of common primary and secondary amides is avoided, the number of steps is fewer, the operation is simple and convenient, the efficiency is high, the selectivity is good, and the economic and environment-friendly effects are realized; the application range of the primer is very broad, and the atom economy is good. The amide compound prepared by the preparation method is a fully novel amide compound, has a broad application range, and can solve the problems of complicated synthesis reaction and narrower primer application range in the existing amide compound.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an amide compound and its preparation method and application. Background technique [0002] Alkynes are a very general class of functional groups, ubiquitous from common simple synthetic building blocks, to synthetic intermediates, biomolecules, and natural products. The ubiquity of carbon-carbon triple bonds has also stimulated long-standing research interest in this type of functional group, including laboratory and industrial synthesis. Since the emergence of the Sonogashira reaction using palladium and copper synergistic catalysis in the 1970s, the synthesis of alkynes has made great progress, and has developed in the direction of atom and step economy. As an important class of alkynes, o-amidoarylacetylenes can not only be used as key intermediates to rapidly synthesize complex molecules through the Diels-Alder reaction, but also the potential biological activity ...

AI Technical Summary

Problems solved by technology

However, on the one hand, the reaction conditions of the above-mentioned literature are relatively harsh (the substrate reaction scale is 0.1 mmol, 120 ° C, 24 h), the substrate needs to be pre-installed with additional directing groups and it is difficult to transform or eliminate, and the reaction requires additional preparation difficulties. And the alkynylation reagent (Waser reagent) of expensive hypervalent iodine, therefore, this catalytic system obviously does not have practicability and economic value, has limited the further application of this method; On the other hand, with respect to nitrogen atom, oxygen The planarity of the atoms is relatively poor, and the complexation of the oxygen atom to the metal in the amide compound is weak, which makes it difficult for the subsequent functional groups to achieve high conversion even if the compound is reversibly coordinated with the metal catalyst. , that is, the challenges faced by the alkynylation reaction of such compounds with carbon-hydrogen bonds: difficult to coordinate, easy to dissociate

[0005] Therefore, the synthesis method of traditional amide compounds is often based on the coupling reaction of functional groups such as carbon-halogen bonds, or groups such as pyridine or quinoline are pre-installed on the amide nitrogen atom to promote the activity and regioselectivity of the reaction. The group is worthless in the synthesis. For the subsequent practical application, it must be removed again at the end of the reaction. The traditional synthesis method is multi-step synthesis, the reaction is complicated, and the scope of substrate application is narrow, which makes them suitable for industrial application. are greatly restricted

Images