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Bis alpha-cyanoimino substituted isochroman compound and synthetic method thereof

A technology of cyanoimine and isochroman, which is applied in the field of bis-cyanoimine replacing isochroman compounds and its synthesis, can solve the problems of complex substrates, toxic cyanide, cumbersome operation, etc., and achieve high The effect of reactivity, simple raw materials, and simple operation

Inactive Publication Date: 2017-08-22
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] (2) Yamamoto et al. used oxime compounds as substrates, first converted them into mesylate, and then completed intramolecular migration and molecular N-pentyl-alpha-hexyl iminonitrile has been synthesized, but the method is cumbersome to operate (seeing references: Yamamoto, H.et.al, J.Am.Chem.Soc., 1983,105,2831 )
[0018] In summary, there are mainly the above methods for the synthesis of α-cyanoimine compounds, but most of them are multi-step reactions, complex substrates and involve toxic cyanides, or use relatively harsh conditions

Method used

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  • Bis alpha-cyanoimino substituted isochroman compound and synthetic method thereof
  • Bis alpha-cyanoimino substituted isochroman compound and synthetic method thereof
  • Bis alpha-cyanoimino substituted isochroman compound and synthetic method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Example 1: N, N'-di-tert-butyl isochroma-1,1-bis(formamimidino) dicyanide

[0034] N, N'-di-tert-butyl isochroma-1,1-bis(carboxamidino) dicyanide adopts the following steps: 1. Add 9.4 grams of isochroman, 17.4 grams of tert-butyl isocyanide, 1.8 grams of Silver trifluoromethanesulfonate, 15.9 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 700 ml of chlorobenzene, heated to 80°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 Analysis (petroleum ether: ethyl acetate=100:1) purification, obtains 14.71 grams of N, N'-di-tert-butyl isochromatic-1,1-bis(formamidinyl) dicyanide, its structural formula is: The yield was 60%. Melting point: 114°C.

[0035] IR(KBr,cm -1 ):2979,2216,1643,1476,1464,1208,914,75...

Embodiment 2

[0040] Example 2: N, N'-di-tert-butyl-5-methylisochroma-1,1-bis(formamimidino) dicyanide

[0041] N, N'-di-tert-butyl-5-methyl isochromatic-1,1-bis(formamimidino) dicyanide adopts the following steps: 1. add 10.4 grams of 5-methyl in a 1000 ml reaction kettle Isochroman, 17.4 g tert-butylisonitrile, 3.6 g silver triflate, 15.9 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 700 ml chlorobenzene, heating to 80°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 Analysis (petroleum ether: ethyl acetate=100:1) purified to obtain 19.12 grams of N, N'-di-tert-butyl-5-methylisochromatic-1,1-bis(formamimidino) dicyanide, Its structural formula is: The yield was 75%. Melting point: 104°C.

[0042] IR(KBr,cm -1 ):2976,2...

Embodiment 3

[0047] Example 3: N, N'-di-tert-butyl-7-phenyl isochroma-1,1-bis(formamimidino) dicyanide

[0048] N, N'-di-tert-butyl-7-phenyl isochromatic-1,1-bis(formamimidino) dicyanide adopts the following steps: 1. add 14.7 grams of 7-benzene in a 1000 ml reaction kettle Isochroman, 17.4 g tert-butylisonitrile, 2.7 g silver triflate, 15.9 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 700 ml chlorobenzene, Heat to 80°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 Analysis (petroleum ether: ethyl acetate = 100:1) purification, to obtain 23.87 grams of N, N'-di-tert-butyl-7-phenylisochromatic-1,1-bis(formamimidino) dicyanide , whose structural formula is: The yield was 80%. Melting point: 125°C.

[0049] IR(KBr,cm -1...

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Abstract

The invention relates to a bis alpha-cyanoimino substituted isochroman compound. The structural formula of the compound is as shown in the specification. Raw materials used in the method are simple and easily available. Under the action of DDQ, tert-butyl isocyanide is used as a cyano source of the reaction and shows high reaction activity under the catalysis of silver trifluoromethanesulfonate. During the reaction process, the operation is simple, conditions are mild, the method is environment-friendly, and yield is generally medium. The generated product has a special bis alpha-cyanoimino substituted skeleton. A series of chemical conversion can be carried out to generate various substituted isochroman derivatives. Therefore, the compound of the invention has a good development prospect in industrial production.

Description

technical field [0001] The invention relates to a bis-alpha-cyanoimine substituted isochroman compound and a synthesis method thereof. Background technique [0002] Heterochroman is a class of heterocyclic compounds that have attracted much attention, and it exists widely in nature as the basic ring system of some antibiotics. Among them, the isochromans that are substituted simultaneously in the aromatic ring and the dihydropyran ring are widely used. These compounds have the effects of anti-inflammatory, analgesic, hypotensive and anti-tumor properties, which have aroused people's strong interest ( See references: Andrieux, J. et al Bull. Soc. chim. Fr. 1973, 3421). Many spices with a heterochromatic ring structure are called heterochromatic spices. The most outstanding representative is Jiale musk; cannabinol, which is clinically used for pain relief, also has a heterochromatic ring. It is derived from the female flower strain of cannabis and extracted from flower spike...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/76C07D311/92C07D407/04C07D311/80
CPCC07D311/76C07D311/80C07D311/92C07D407/04
Inventor 许斌迟惠文李浩赵雷阳刘秉新
Owner SHANGHAI UNIV
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