5-(benzofuran-2-carbonyl)-6-carboxamide-5,6-dihydro-phenanthridine derivative and synthesis and application thereo

Abstract

The invention relates to a 5-(benzofuran-2-carbonyl)-6-carboxamide-5,6-dihydro-phenanthridine derivative and synthesis and application thereof. Firstly, benzofuran-2-formamide is obtained through Ugi reaction of arylamine, 2-bromoacetic acid, 2-bromobenzaldehyde and substituted isonitrile and subsequent microwave-assisted Rap-Stoermer reaction; and then, a reactant (benzofuran-2-formamide), a metal palladium catalyst, a ligand, an additive and alkali are added to an anhydrous organic solvent, and the mixture is heated, reacted and subjected to aftertreatment after reaction is completed to obtain the high-purity 5-(benzofuran-2-carbonyl)-6-carboxamide-5,6-dihydro-phenanthridine derivative. In the preparation method provided by the invention, the raw materials are simple and easy to obtain, the operation is easy and convenient, aftertreatment is easy, diversified substituents are easy to obtain, and the generated compound contains two important heterocyclic structures of benzofuran-2-formamide and dihydro-phenanthridine simultaneously, and can well meet the demand for screening of pharmaceutical activity, thereby having good application and market values in the preparation of anti-hepatitis B virus medicaments.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, and specifically relates to a 5-(benzofuran-2-carbonyl)-6-carboxamide-5,6-dihydrophenanthridine derivative and its synthesis and application. Background technique [0002] Dihydrophenanthridine and its derivatives are not only an important class of organic synthesis intermediates, but also the structural units of many phenanthridine alkaloids with physiological activity, so they have attracted widespread attention. (References: (a) Harayama, T.; Akiyama, T.; Akamatsu, H.; Kawano, K.; Abe, H.; Takeuchi, Y. Synthesis 2001, 2001, 444; (b) Donaldson, L.R.; Haigh, D.; Hulme, A.N. Tetrahedron 2008, 64, 4468; (c) Yang, C.H.; Cheng, M.-J.; 71,669; Bioorg.Med.Chem.Lett., 2012,22,3095) For example, the compound Lycorine (lycorine) containing dihydrophenanthridine structure has a strong emetic effect, and the compound Chelidonine (chelidonine) can be used Pain relief for gastrointestinal co...

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Problems solved by technology

[0006] In recent years, great progress has been made in the synthesis of benzofuran derivatives and dihydrophenanthridine derivatives, but for 5-(benzofuran-2-carbonyl) containing these two important active structures )-6-carboxamide-5,6-dihydrophenanthridine compounds design and synthesis, especially the use of simple and easy-to-obtain raw materials to synthesize such compounds has not been reported

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