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6-(alpha-cyanoimine) based phenidine compound and synthesis method thereof

A cyanoimine and compound technology, applied in the field of 6-phenanthridine compounds and their synthesis, can solve problems such as limited types of compounds, and achieve the effects of good application prospects, simple raw materials and high reactivity

Inactive Publication Date: 2019-03-08
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] At present, there are mainly the above methods for the synthesis of phenanthridine compounds, but the types of compounds that can be synthesized by the above methods are still relatively limited, and new synthesis methods still need to be developed for some compounds with special substituents

Method used

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  • 6-(alpha-cyanoimine) based phenidine compound and synthesis method thereof
  • 6-(alpha-cyanoimine) based phenidine compound and synthesis method thereof
  • 6-(alpha-cyanoimine) based phenidine compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: (Z)-N-(tert-butyl)phenanthridine-6-methanimine cyanide

[0044] (Z)-N-(tert-butyl)phenanthridine-6-methylimine cyanide adopts the following steps: 1. add 15.9 grams of N-p-toluenesulfonyl-5,6-dihydrophenanthrene in a 1000 ml reactor Pyridine, 20.1 ml tert-butylisonitrile, 1.74 g silver triflate, 30.6 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 675 ml chlorobenzene, heated to 80 ℃. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, extract the product with ethyl acetate, wash with saturated brine, and remove the solvent with a rotary evaporator after drying to obtain a crude product; ③ Use a column layer for the crude product Analyze (petroleum ether: ethyl acetate=20:1) purify, obtain 8.8 gram (Z)-N-(tert-butyl)phenanthridine-6-methanimine cyanides, its structural formula is: The yield was 68%. Melting point: 103-105°C.

[0045] IR(KBr,cm -1 ):3075,2975,2217,1612,1450,1362,1207,937;

[0...

Embodiment 2

[0050] Example 2: (Z)-N-(tert-butyl)-8-methylphenanthridine-6-methanimine cyanide

[0051] (Z)-N-(tert-butyl)-8-methylphenanthridine-6-methylimine cyanide adopts the following steps: 1. add 15.6 grams of N-p-toluenesulfonyl-5 in 1000 milliliters of reaction kettle, 6-dihydro-8-methylphenanthridine, 25.2 ml tert-butylisonitrile, 1.74 g silver triflate, 15.9 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone , 450 ml of chlorobenzene, heated to 90°C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, extract the product with ethyl acetate, wash with saturated brine, and remove the solvent with a rotary evaporator after drying to obtain a crude product; ③ Use a column layer for the crude product Analyze (petroleum ether: ethyl acetate=20:1) purify, obtain 7.18 grams of (Z)-N-(tert-butyl)-8-methylphenanthridine-6-methanimine cyanide, its structural formula is: The yield was 53%. Melting point: 158-160°C.

[0052] IR(...

Embodiment 3

[0057] Example 3: (Z)-8-bromo-N-(tert-butyl)phenanthridine-6-methanimine cyanide

[0058] (Z)-N-(tert-butyl)-8-bromophenanthridine-6-methylimine cyanide adopts the following steps: ①add 18.6 grams of N-p-toluenesulfonyl-5,6 in a 1000 ml reaction kettle -Dihydro-8-bromophenanthridine, 20.1 ml tert-butylisonitrile, 1.74 g silver triflate, 30.6 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 450 mL of chlorobenzene, heated to 85°C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, extract the product with ethyl acetate, wash with saturated brine, and remove the solvent with a rotary evaporator after drying to obtain a crude product; ③ Use a column layer for the crude product Analyze (petroleum ether: ethyl acetate=20:1) purify, obtain 5.18 gram (Z)-N-(tert-butyl)-8-methylphenanthridine-6-methanimine cyanides, its structural formula is: The yield was 31%. Melting point: 172-174°C.

[0059] IR(KBr,cm -1 ):2967.0...

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Abstract

The invention relates to an alpha-cyanoimine substituted phenidine compound. A structural formula of the compound is shown as follows. The compound is an organic synthesis intermediate of great value,a phenidine framework already shows diverse bioactivity, so that the compound can be converted into corresponding other active compounds. The method is simple and easy-to-get in raw material, t-butylisonitrile is adopted as a cyano source of reaction, and high reaction activity is presented under catalysis of silver trifluoromethanesulfonate; the reaction process is simple in operation, mild in condition, environment-friendly and common to moderate in yield, therefore, the compound has great development prospect in industrial production.

Description

technical field [0001] The invention relates to a 6-(alpha-cyanoimino)phenanthridine compound and a synthesis method thereof. Background technique [0002] Phenanthridine compounds are a class of very valuable organic compounds that widely exist in natural products. Because of its good biological activity and photoelectric activity, it is widely used in the fields of medicinal chemistry and organic functional materials. For example, Shamma et al. extracted nearly a hundred natural products containing phenanthridine skeletons from various plants (see reference: Shamma, M. et al, J. Nat. Prod. 1984, 47, 1). Bastida et al. extracted Trisphaeridin, a compound containing a phenanthridine skeleton, from Asturias narcissus (see reference: Bastida, J. et al, Planta Med. 1997, 63, 583). Chai et al. synthesized a variety of chelerythrine analogs and tested their inhibitory activity on Bcl-XL and Bak peptides. The results showed that three new compounds showed higher inhibitory activ...

Claims

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Application Information

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IPC IPC(8): C07D221/12C07F7/08
CPCC07D221/12C07F7/0812
Inventor 许斌李浩叶容瑄刘秉新谭启涛
Owner SHANGHAI UNIV
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