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A kind of synthetic method of polycyclic compound containing indoline structure

An indoline structure, polycyclic compound technology, applied in organic chemistry methods, organic chemistry and other directions, can solve the problems of difficult reuse of catalysts, complicated product separation steps, complicated reaction raw materials, etc., and achieves good functional group adaptability, easy to use. Separation and purification, the effect of a wide range of sources

Active Publication Date: 2022-04-05
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above methods all need to use complex catalysts and special reaction raw materials, which affect their practical performance.
[0004] It can be seen that the current methods for constructing polycyclic compounds containing indoline structures require multi-step reactions, complex precursor structures, or the introduction of additional additives. In addition, these reaction systems all use homogeneous catalytic systems with complex structures , there are disadvantages such as difficulty in reusing the catalyst and complicated product separation steps

Method used

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  • A kind of synthetic method of polycyclic compound containing indoline structure
  • A kind of synthetic method of polycyclic compound containing indoline structure
  • A kind of synthetic method of polycyclic compound containing indoline structure

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Experimental program
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Effect test

Embodiment 1-3

[0042] Using the prepared layered double metal hydroxide catalyst M 2+ x m 3+ -LDHs, catalyzing the reaction system of tetrahydroisoquinoline compound 1 and active methylene compound 2, the specific operation steps are as follows:

[0043] Weigh the prepared catalyst 0.2g, 2-phenyl-1,2,3,4-tetrahydroisoquinoline (1a) 0.5mmol, malononitrile (2a) 3mmol, temperature at 80°C, oxygen flow rate 5mL / min , the solvent is 2ml of 1,4-dioxane, and the reaction time is 20h. In the reaction solution, the raw material 2-phenyl-1,2,3,4-tetrahydroisoquinoline and the product 5,12a-dihydroindo[2,1-a]isoquinoline-12,12(6H)- The content analysis of diformonitrile (3aa) adopts 1 H-NMR internal standard method (1,4-dinitrobenzene as internal standard), calculate the conversion rate and selectivity of the reaction.

Embodiment 1

[0044] The layered double metal hydroxide catalyst adopted in embodiment 1 is CuCoFe-LDH, the layered double metal hydroxide catalyst adopted in embodiment 2 is CuMnAl-LDH, the layered double metal hydroxide catalyst adopted in embodiment 3 The metal hydroxide catalyst is CuCo 2 Fe-LDH.

Embodiment 4

[0053] Weigh 0.2 g of the prepared CuCoFe-LDH catalyst, 0.5 mmol of 2-phenyl-1,2,3,4-tetrahydroisoquinoline, 3.0 mmol of malononitrile, temperature at 40°C, oxygen flow rate of 5 mL / min, solvent 1,4-dioxane 2ml, the reaction time is 36h. In the reaction solution, the raw material 2-phenyl-1,2,3,4-tetrahydroisoquinoline and the product 5,12a-dihydroindo[2,1-a]isoquinoline-12,12(6H)- The content analysis of dicyanonitrile adopts 1 H-NMR internal standard method (1,4-dinitrobenzene as internal standard), calculate the conversion rate and selectivity of the reaction. The conversion of 1a was 96.9%, and the selectivity of 3aa was 32.6%.

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Abstract

The invention discloses a new method for synthesizing polycyclic compounds containing indoline structures, adding tetrahydroisoquinoline compounds 1, active methylene compounds 2, and layered double metal hydroxide catalysts into a reactor and an organic solvent, pass through an oxygen-containing gas, and react under stirring and heating conditions. After the reaction is completed, the compound 3, which is the target product, is obtained through post-processing. The preparation method of the present invention uses layered double metal hydroxide as a catalyst, tetrahydroisoquinoline derivatives and active methylene compounds cascade C-C coupling reaction to construct polycyclic compounds containing indoline structure , a reaction pathway involving cross-dehydrogenation coupling and coupling cyclization, with good functional group adaptability. The catalyst used is a heterogeneous catalyst, oxygen is used as an oxidant, no additives are needed, the reaction system is simple to operate, the economy is good, and the product is easy to separate and purify.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing polycyclic compounds containing an indoline structure. Background technique [0002] Indoline-containing polycyclic compounds are important structural units in many natural products, drug molecules, and bioactive molecules. Therefore, the development of effective synthetic strategies for the construction of indoline-containing polycyclic compounds has attracted extensive attention from organic chemistry. home attention. [0003] Dihydroindolotetrahydroisoquinoline is an important structural unit of the natural products claucarine, cluckaroline and biologically active molecules. Coupling reaction (Scheme 1-i), this method needs to often need multi-step reaction and complex catalytic system (T.Kametani, K.Ogasawara, J.Chem.Soc., 1967,2208-2212; A.I.Meyers, T.M. Sielecki, D.C. Crans, R.W. Marshman, H. Nguyen, J. Am. Chem. Soc. 1992, 114, 8483-84...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07D471/10
CPCC07D471/04C07D471/10C07B2200/13
Inventor 周维友王安玮孔臻极夏珍珍田晓婷何明阳陈群
Owner CHANGZHOU UNIV