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A kind of synthetic method of phenanthridinone compound

A synthesis method and compound technology, which are applied in the field of synthesis of phenanthridinone compounds, can solve the problems of complex synthesis steps of starting materials, limited types of synthesis products, and low yield of synthesis routes, and achieve easy operation, mild reaction conditions, The effect of simple process steps

Active Publication Date: 2021-07-09
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the traditional synthetic method, the synthetic steps of the starting materials used are complicated, the yield of the synthetic route is low, the raw materials are expensive and not easy to obtain, and the types of synthetic products are limited

Method used

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  • A kind of synthetic method of phenanthridinone compound
  • A kind of synthetic method of phenanthridinone compound
  • A kind of synthetic method of phenanthridinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of compound intermediate (I-1)

[0042] 0.2mmol 2-methyl-benzoyl-8-quinolinamine, 0.4mmol benzyne precursor, 0.07mmol Cu(OAc) 2 , 0.24mmol cesium fluoride, 0.1mmol tetrabutylammonium iodide, 1mL N,N-dimethylformamide, 1mL MeCN were added to the reaction flask, purged with oxygen, sealed and heated to 80°C for 12h, cooled to room temperature Afterwards, the compound (I-1) was obtained as colorless crystals after distillation and purification under reduced pressure, with a yield of 37%.

[0043] Compound (I-1) is:

[0044] 1 HNMR (CDCl 3,400MHz,ppm):δ8.80(dd,J=4.2,1.7Hz,1H),8.33-8.26(m,3H),8.04-8.00(m,1H),7.77-7.73(m,2H),7.66 (t, J=7.8Hz, 1H), 7.44-7.41(m, 1H), 7.40(d, J=7.4Hz, 1H), 7.21(td, J=7.2, 1.4Hz, 1H), 7.14(td, J=8.5, 1.6Hz, 1H), 6.37(dd, J=8.2, 1.0Hz, 1H), 2.91(s, 3H); 13 CNMR (CDCl 3 ,100MHz,ppm)δ162.97,151.54,144.84,143.34,139.77,136.80,136.49,136.15,132.03,131.89,130.85,130.02,129.33,129.05,127.04,124.61,123.56,122.28,122...

Embodiment 2

[0045] Embodiment 2: the preparation of compound intermediate (I-2)

[0046] 0.2mmol 3-methyl-benzoyl-8-quinolinamine, 0.4mmol benzyne precursor, 0.07mmol Cu(OAc) 2 , 0.24mmol cesium fluoride, 0.1mmol tetrabutylammonium iodide, 1mL N,N-dimethylformamide, 1mL MeCN were added to the reaction flask, purged with oxygen, sealed and heated to 80°C for 12h, cooled to room temperature Afterwards, the compound (I-2) was obtained as colorless crystals after distillation and purification under reduced pressure, with a yield of 57%.

[0047] Compound (I-2) is:

[0048] 1 HNMR (CDCl 3 ,400MHz,ppm):δ8.78(dd,J=4.2,1.7Hz,1H),8.37(s,1H),8.31-8.25(m,3H),8.02(dd,J=7.0,2.7Hz,1H ),7.77-7.72(m,2H),7.63(dd,J=8.3,1.7Hz,1H),7.42-7.39(m,1H),7.23(td,J=8.4,2.3Hz,1H),7.15( td,J=8.4,1.5Hz,1H),6.47(dd,J=8.3,1.0Hz,1H),2.52(s,3H); 13 CNMR (CDCl 3 ,100MHz,ppm)δ162.20,151.50,144.76,139.36,138.22,136.43,134.21,132.11,130.72,129.94,129.47,129.00,128.66,126.90,126.02,122.96,122.52,122.03,119.41,116.95,21....

Embodiment 3

[0049] Embodiment 3: the preparation of compound intermediate (I-3)

[0050] 0.2mmol 4-methyl-benzoyl-8-quinolinamine, 0.4mmol benzyne precursor, 0.07mmol Cu(OAc) 2 , 0.24mmol cesium fluoride, 0.1mmol tetrabutylammonium iodide, 1mL N,N-dimethylformamide, 1mL MeCN were added to the reaction flask, purged with oxygen, sealed and heated to 80°C for 12h, cooled to room temperature Afterwards, the compound (I-3) was obtained as colorless crystals after distillation and purification under reduced pressure, with a yield of 70%.

[0051] Compound (I-3) is:

[0052] 1 HNMR (CDCl 3 ,400MHz,ppm):δ8.78(dd,J=4.2,1.7,1H),8.46(d,J=8.1Hz,1H),8.33(dd,J=7.9,1.4Hz,1H),8.26(dd ,J=8.3,1.7Hz,1H),8.17(s,1H),8.02(dd,J=7.2,2.5Hz,1H),7.78-7.72(m,2H),7.44-7.40(m,2H), 7.25-7.21(m,1H),7.19-7.15(m,1H),6.47(dd,J=8.2,1.0Hz,1H),2.60(s,3H); 13 CNMR (CDCl 3 ,100MHz,ppm)δ162.18,151.54,144.84,143.36,139.88,136.42,134.58,130.78,129.94,129.51,129.46,129.29,129.02,126.91,123.95,123.15,122.45,122.07,122.03,1...

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Abstract

The present invention relates to a kind of synthetic method of phenanthridine ketone compound, and this method is that the benzamide with directing group and benzyne precursor, under the joint action of catalyst, inorganic base, additive, solvent and oxygen, carry out carbon ‑Hydrogen bonds and nitrogen‑hydrogen bonds activate the cyclization reaction to generate the core skeleton of phenanthridinone compounds, and then remove the directing group to synthesize phenanthridinone compounds. Compared with the prior art, the method of the present invention adopts cheap, easy-to-get and environment-friendly copper catalyst, avoids the use of rare metals in the reaction process, such as catalysts such as ruthenium, rhodium, palladium, etc., the substrate has diversity, and the reaction conditions are relatively mild, which can The reproducibility is good, and the method of the present invention can be used to synthesize natural products of phenanthridinones such as Phenaglydon and Crinasiadine, which provides a new idea for the synthesis of phenanthridones and the synthesis of natural products of Amaryllidaceae alkaloids, and has a good Application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a method for synthesizing phenanthridinone compounds. Background technique [0002] Phenanthridinone alkaloids widely exist in nature. As a class of highly active natural products, many molecules and their derivatives have shown good physiological activities in cardiovascular system diseases, as well as anticancer, antibacterial and antiviral aspects. Therefore, the development of new synthetic methods for phenanthridinone alkaloids and their derivatives has always been a hot topic in organic synthetic chemistry and has broad market prospects. [0003] In the traditional synthetic method, the synthetic steps of the starting materials used are complicated, the yield of the synthetic route is low, the raw materials are expensive and not easy to obtain, and the types of synthetic products are limited. For example, the Chinese invention patent with the application n...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/12C07D491/056
CPCC07D221/12C07D491/056
Inventor 张书宇张婷玉丁同梅
Owner SHANGHAI JIAOTONG UNIV