Preparation method of 2, 3-naphthalimide derivative

Abstract

The invention belongs to the field of organic synthesis, and discloses a preparation method of a 2, 3-naphthalimide derivative, which mainly comprises the following didehydrogenation DA reaction steps: reacting an alkyne amide derivative with an alkaline substance, and then reacting with a cinnamyl chloride derivative to prepare the 2, 3-naphthalimide derivative. Compared with the prior art, the preparation method of the 2, 3-naphthalimide derivative has the advantages that the defects of tedious steps, complicated synthesis route, harsh reaction conditions, limited substrate range and low yield of the preparation method of the 2, 3-naphthalimide derivative can be effectively overcome by improving the synthesis route, the overall flow process design of the preparation method and the like; the method provided by the invention has the advantages of mild reaction conditions, easily available initial raw materials, short reaction route, easily operated reaction, high reaction speed, good reaction selectivity, wide reaction substrate range, high reaction yield and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and more specifically relates to a preparation method of 2,3-naphthalimide derivatives. Background technique [0002] Naphthalimides are a very important class of heterocyclic compounds, which widely exist in pharmaceutically active compounds, agricultural chemicals and fluorescent materials. Naphthalimide plays an important role in dyes, molecular probes, sensing technologies, etc. (see: ACSChemical Biology 2008,3,142; Dyes and Pigments 1989,11,13.), substances containing naphthalimide structure usually have Fluorescent properties. The fluorescent properties of naphthalimide originate from the "push-pull electron" structure formed by the electron-donating group and the imide structure, which makes the electrons in it easily transition, thereby generating fluorescence. The fluorescence properties of the naphthalimide derivatives can be changed by changing the groups attached to the naphthalimide...

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Problems solved by technology

[0004] For the above defects or improvement needs of the prior art, the object of the present invention is to provide a kind of preparation method of 2,3-naphthalimide derivatives, wherein by Improve the synthesis route, the overall flow process design of the preparation method, and the parameter conditions (such as the ratio of reaction raw materials and reaction temperature) used in each reaction step. As the starting material, after the hydrogen extraction of the base, the target ring-closing product is directly generated by forming an imide derivative intermediate and then continuing the intramolecular ring-closing reaction, thereby obtaining 2,3-naphthoimide derivatives, Compared with the prior art, it can effectively solve the defects of cumbersome steps in the preparation method of naphthalimide derivatives, complex synthetic routes, harsh reaction conditions, limited substrate range, and low yield. The synthetic route and synthetic method in the present invention have the advantages of reaction The starting materials are easy to obtain, the reaction operation is simple, the steps are concise, the synthetic route is short, the yield of the target product is high, the substrate range is wide, the reaction speed is fast, the reaction selectivity is good, and the reaction conditions are mild.

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