Synthetic method for phenanthridone compound

A synthesis method and compound technology are applied in the field of synthesis of phenanthridine compounds, and can solve the problems of complex synthesis steps of starting materials, limited types of synthesis products, low yield of synthesis routes, etc., and achieve easy operation, mild reaction conditions, Simple process steps

Active Publication Date: 2018-07-31
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Synthetic method for phenanthridone compound
  • Synthetic method for phenanthridone compound
  • Synthetic method for phenanthridone 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 invention relates to a synthetic method for a phenanthridone compound. The method comprises the following steps: subjecting benzamide with a guiding group and a benzyne precursor to carbon-hydrogen bond and nitrogen-hydrogen bond activation and cyclization under the co-action of a catalyst, an inorganic base, an additive, a solvent and oxygen so as to produce the core skeleton of the phenanthridone compound; and then removing the guiding group so as to synthesize the phenanthridone compound. Compared with the prior art, the invention has the following advantages: the cheap, easily available and environment-friendly copper catalyst is used, and rare metal catalysts like ruthenium, rhodium and palladium are not used in the reaction; a substrate has diversity; reaction conditions are mild; and the method has good repeatability. The method provided by the invention can synthesize natural phenanthridone products like Phenaglydon and Crinasiadine, provides a new idea for synthesis of phenanthridone compounds and natural amaryllidaceae alkaloid products, and has good application prospects.

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 Applications(China)
IPC IPC(8): C07D221/12C07D491/056
CPCC07D221/12C07D491/056
Inventor 张书宇张婷玉丁同梅
Owner SHANGHAI JIAO TONG UNIV
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