5-(benzofuran-2-carbonyl)-6-carboxamide-5,6-dihydro-phenanthridine derivative and synthesis and application thereo
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A technology of benzofuran and dihydrophenanthridine, which is applied in the field of 5--6-carboxamide-5, can solve the problems that have not been reported, and achieve the effects of low preparation cost, high research value, and efficient synthesis process
Active Publication Date: 2017-12-15
宝利化(南京)制药有限公司
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[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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Embodiment 1
[0030] 5-(benzofuran-2-carbonyl)-6-carboxamide-5,6-dihydrophenanthridine derivatives, the chemical structure of which is shown in formula VI:
[0031]
[0032] Representative compound VI-a (R in the formula VI 1 is hydrogen; R 2 is cyclohexyl; R 3 For hydrogen) the synthetic steps are as follows:
[0033]
[0034] Benzofuran-2-carboxamide (0.20mmol) and palladium acetate (10mol%), tricyclohexylphosphine fluoroborate (20mol%), pivalic acid (PivOH) (30mol%) and potassium carbonate (0.40mmol%) ) into the microwave tube, then cover the lid, pump nitrogen three times on the oil pump. Pour degassed anhydrous N,N-dimethylacetamide (4mL) into the microwave tube, heat the reaction in an oil bath to 110°C and stir for 4 hours. Filter while washing with ethyl acetate. The filtrate was dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography with ethyl acetate and petroleum ether (ethyl acetate / petroleum ether=1 / 10) to obtain the target compound...
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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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