Synthesis method of triazole quinoline derivative

Abstract

The invention relates to a synthesis method of a triazole quinoline derivative and belongs to the technical field of organic and medicine synthesis. The method is characterized in that the triazole quinoline derivative is obtained through a one-pot reaction of o-bromobenzene triazole and terminal alkyne under the action of a copper salt catalyst. The synthesis method has the benefits as follows: cheap and easy-to-obtain copper salt is taken as the catalyst, o-bromobenzene triazole and terminal alkyne are subjected to the one-pot reaction, the reaction conditions are mild, the yield is high, raw materials are easy to obtain, and a triazole quinoline compound is effectively and conveniently synthesized. Compared with an existing method, the synthesis method has the advantages that the reaction yield is increased through copper salt catalysis, the reaction conditions are milder, the safety is good, the operation is simple and convenient, the substrate range is wide, the reaction efficiency is high, the catalyst is low in cost, the reaction time is shorter than 24 hours taken by a Gulevskaya research group, and the method has potential application value.

Description

technical field [0001] The invention relates to a synthesis method of triazole isoquinoline derivatives, belonging to the technical field of organic and pharmaceutical synthesis. [0002] technical background [0003] Due to its unique core structure, N-containing fused heterocyclic compounds show potential biological and pharmaceutical activities, and are widely used in various fields such as pesticides, materials, dyes, biology and medicine. [0004] Therefore, it remains a great challenge to synthesize complex fused heterocyclic compounds from simple small molecules by facile, mild and efficient synthetic methods. [0005] In 2013, Kundu's research group found that triazole isoquinolines were synthesized by stepwise condensation / [3+2] cycloaddition of o-alkynyl benzaldehyde compounds, but this method required the isolation of the intermediate product (E)-1 -(2-nitrovinyl)-2-alkynylbenzene (obtained by the reaction of o-alkynyl benzaldehyde and nitromethane), at the same t...

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Problems solved by technology

[0004] Therefore, it remains a great challenge to synthesize complex fused heterocyclic compounds from simple small molecules using simple, mild and efficient synthetic methods.

[0005] In 2013, Kundu's research group found that triazole isoquinolines were synthesized by stepwise condensation / [3+2] cycloaddition of o-alkynyl benzaldehyde compounds, but this method required the isolation of the intermediate product (E)-1 -(2-nitrovinyl)-2-alkynylbenzene (obtained by the reaction of o-alkynyl benzaldehyde and nitromethane), at the same time, the intermediate product (E)-1-(2-nitrovinyl )-2-alkynylbenzene structure restriction, only R 2 = product of H with a maximum yield of 88%

Later, the Gulevskaya research group found that the corresponding triazole pyridine derivatives and triazole isoquinoline derivatives could be obtained through the reaction of enediynes and sodium azide, but when the substitution on the diynes of enediynes When the bases are different, the yield and regioselectivity of the method are very low, and the method cannot be widely applied

[0006] In summary, the above methods for synthesizing triazole isoquinoline derivatives all have the problems of rare raw materials, low yield, and few suitable substrates.

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