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Synthesis method of (R) 3-amino-2-oxoindole derivative

A compound, the technology of dioxane, applied in the field of synthesis of chiral-3-amino-2-oxidole derivatives, can solve problems such as harmfulness and ineffectiveness, achieve mild reaction conditions, broaden the scope of application, and be suitable for industrialization The effect of mass production

Inactive Publication Date: 2017-09-05
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With chiral drugs, one isomer may be effective while the other may be ineffective or even harmful

Method used

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  • Synthesis method of (R) 3-amino-2-oxoindole derivative
  • Synthesis method of (R) 3-amino-2-oxoindole derivative
  • Synthesis method of (R) 3-amino-2-oxoindole derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Example 1: Add 0.2 mmol of the compound of formula 1a and 0.1 mmol of the compound of formula 2a in 1 ml of 1,4-dioxane as reactants, 100 mg Molecular sieve is used as an additive, 0.01 millimole of chiral phosphoric acid (that is, the compound of formula 4 in this patent) is used as a catalyst, and the corresponding (R) 3-amino-2-oxindole derivative is obtained by reacting at 50° C. for 48 hours.

[0034]

Embodiment 1-11

[0036] Attached below figure 1 And attached figure 2 And embodiment further describes the present invention:

[0037] Reaction raw materials, reaction conditions and productive rate are as shown in table 1:

[0038] Table 1*

[0039]

[0040]

[0041] * 0.2 mmol of compound of formula 1 and 0.1 mmol of compound of formula 2a were used as reactants, 0.01 mmol of compound of formula 4 was used as catalyst, and 1 ml of 1,4-dioxane was used as solvent.

[0042] In table 1, the isatin imine of embodiment 1~9 reaction is the isatin imine of 4-7 position substitution, and the isatin imine of embodiment 10 reaction is the isatin imine of ester group protection, and embodiment 11 reaction The isatinimines are different N-benzyl substituted isatinimines.

Embodiment 12-11

[0044] Reaction raw materials, reaction conditions and productive rate are as shown in table 2:

[0045] Table 2*

[0046]

[0047] * 0.2 mmol of isatinimine 1a and 0.1 mmol of enaminone 2 were used as reactants, and 0.01 mmol of chiral phosphoric acid 4 was used as catalyst.

[0048] In Table 2, the enaminones reacted in Examples 12-21 are the enaminones of damidones derived from various anilines, and the enaminones reacted in Example 22 are enaminones of dammidones derived from naphthylamine.

[0049] As can be seen from Table 1 and Table 2, the method of the present invention can not only realize the diversity and complexity of product molecules in one step, obtain high enantioselectivity, high atom economy, environmental friendliness, and wide application range, but also raw materials are easy to obtain, The operation is simple and safe, the reaction conditions are mild, the reaction time is short, the post-treatment is simple, and the product structure is diversified, ...

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Abstract

The invention relates to a synthesis method of a (R)3-amino-2-oxoindole derivative, in particular to a synthesis method of a (R)-3-amino-2-oxoindole derivative which contains an enaminone skeleton. By the method, diversity and complexity of product molecules can be realized at one step, and high enantioselectivity is achieved; the synthesis method is high in atom economy and wide in application range, and is environmentally friendly; and moreover, raw materials are easy to obtain, the synthesis method is simple and safe to operate, reaction conditions are gentle, reaction time is short, aftertreatment is simple, the structure of the product is diversified, and therefore, the implementing value and the potential social economical benefit are high.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry; it relates to a synthesis method of (R)-3-amino-2-oxindole derivatives, in particular to a chiral (R)-3-amino-2-oxindole derivative containing an enaminone skeleton. Synthetic method of 2-oxindole derivatives. Background technique [0002] Oxindole derivatives are a very important class of nitrogen heterocyclic compounds, which widely exist in natural products and drug molecules, and can be used as antipyretic analgesics, stimulants, antihypertensive drugs, vasodilators, antihistamines, etc. , so the synthesis of such compounds has been widely concerned by chemical and pharmaceutical scientists. However, the synthesis of chiral (R)-3-amino-2-oxindole derivatives containing enaminone skeleton is rarely reported as a new class of compounds. There are many chiral compounds in nature, these chiral compounds have two enantiomers. Enantiomers are a lot like your left and right hands, they ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/40
CPCC07D209/40
Inventor 石枫卞辰瑜万莹王静怡
Owner XUZHOU NORMAL UNIVERSITY
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