A kind of chroman ring derivative and its preparation method

A technology for chroman rings and derivatives, which is applied in the field of chroman ring derivatives and their preparation, can solve problems such as difficult synthesis methods, and achieve broad application prospects and complex and diverse structures

Active Publication Date: 2018-01-09
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although benzopyran compounds and their derivatives are so useful in medicine, their synthesis methods are still difficult to carry out. Most of them are 1, 3, and 4-position substitutions on the ring. As early as 1991, Someone used 3,4-dihydro-2-benzopyrone as the starting material to complete the indole and furan ring derivatives with similar molecular skeletons

Method used

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  • A kind of chroman ring derivative and its preparation method
  • A kind of chroman ring derivative and its preparation method
  • A kind of chroman ring derivative and its preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0036] A chroman ring derivative having the following structural formula:

[0037]

[0038] Its synthesis route is as follows figure 2 shown.

[0039] The preparation method of above-mentioned chroman ring derivative is:

[0040] A. Using 820mmol of sodium hydride as a catalyst, 200mmol of diisopropyl malonate and 440mmol of propargyl bromide were added to 250mL of anhydrous acetonitrile, stirred and reacted in an ice-water bath for 8 hours, the product was washed with water, extracted with ethyl acetate, Spin to dry under reduced pressure, perform column chromatography with ethyl acetate:petroleum ether=1:100 (volume ratio) as the eluent, collect the target product, concentrate and dry to obtain a white solid product, namely compound a-1;

[0041] B. Under anhydrous and oxygen-free conditions, mix 80mmol of compound a-1 with 224mmol of phenylethynyl bromide in 1.5g of Pd(PPh 3 ) 2 Cl 2 / CuI catalytic system, where Pd(PPh 3 ) 2 Cl 2 The ratio of the amount of subst...

Embodiment 2

[0047] A chroman ring derivative having the following structural formula:

[0048]

[0049] Its synthesis route is as follows image 3 shown.

[0050] The preparation method of above-mentioned chroman ring derivative is:

[0051] A. With 820mmol sodium hydride as a catalyst, 200mmol dimethyl malonate and 450mmol propargyl bromide were added to 250mL anhydrous acetonitrile, stirred and reacted in an ice-water bath for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry, and perform column chromatography with ethyl acetate:petroleum ether=1:100 (volume ratio) as the eluent, collect the target product, concentrate and dry to obtain a white solid product, namely compound a-2.

[0052] B. Under anhydrous and oxygen-free conditions, mix 80mmol of compound a-2 with 200mmol of phenylethynyl bromide substituents in 1.3gPd(PPh 3 ) 2 Cl 2 In / CuI catalytic system, use 340mmol triethylamine as base, 200ml anhydrous acetonitrile as solven...

Embodiment 3

[0059] A chroman ring derivative having the following structural formula:

[0060]

[0061] Its synthesis route is as follows Figure 4 shown.

[0062] The preparation method of above-mentioned chroman ring derivative is:

[0063] A. Using 720mmol sodium hydride as a catalyst, add 200mmol dimethyl malonate and 640mmol propargyl bromide into anhydrous acetonitrile, stir and react in an ice-water bath for 11 hours, add water to wash the product, extract it with ethyl acetate, and depressurize Spin to dry, carry out column chromatography with ethyl acetate:petroleum ether=1:80 (volume ratio) as the eluent, collect the target product, concentrate and dry to obtain a white solid product, namely compound a-3;

[0064] B. Under anhydrous and oxygen-free conditions, mix 80mmol of compound a-3 with 240mmol of phenylethynyl bromide in 1.1g of Pd (PPh 3 ) 2 Cl 2 / CuI catalytic system, the molar ratio Pd(PPh 3 ) 2 Cl 2 :CuI=3:1, with 400mmol triethylamine as the base, 140mL anh...

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Abstract

The invention discloses a benzodihydropyran ring derivative and a preparation method thereof. The malonate and propargyl bromide are used as initial raw materials to synthesize a benzodihydropyran ring derivative through a three-step reaction; and the raw material is simple and easy to obtain, the synthesis method is convenient and fast, and an efficient and fast synthesis path is provided for the preparation of the benzodihydropyran ring derivative.

Description

technical field [0001] The invention relates to a chroman dihydropyran ring derivative and a preparation method thereof. Background technique [0002] Benzopyran compounds and their derivatives are a large class of natural products, and their structure is that a benzene ring is connected to a pyran ring, and other groups (such as: hydroxyl, acetyl, etc.) can also be connected on the two six-membered rings. , methyl, carboxyl, etc.), such natural products widely exist in plants in nature, and many of them have good biological activity. At the same time, there are also many flavonoid natural products containing benzopyran ring substituents in nature. Flavonoids and other forms exist. Pharmacological studies have shown that many compounds have various biological activities such as analgesic, anti-cancer, anti-leukemia, anti-fungal, and inhibition of cyclic adenosine phosphodiesterase. They are a large class of natural products with medicinal value. [0003] Although benzopyra...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/77
CPCC07D307/77
Inventor 吕双胡益民
Owner ANHUI NORMAL UNIV
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