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Dibenzanthracene, dinaphthopyran and dibenzanthracene, dinaphtho spiropyran analog compound and its preparation

A technology of benzospiropyran and naphthospiropyran, which is applied in the field of dibenzo, dinaphthospiropyran and dibenzo, dinaphthospiropyran compounds and their preparation, can solve complex steps, The overall yield is low, the raw materials are not easy to obtain, etc., to achieve the effect of simple steps, easy to obtain raw materials, and cheap raw materials

Inactive Publication Date: 2006-12-27
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing reported method for preparing dibenzo and dinaphthopyran compounds is not only difficult to obtain raw materials, complicated steps, and low overall yield, but also the types of these two types of compounds that can be prepared are seldom (Huang, C.- G.; Bereridge, K.A.; Wan, P.J.Am.Chem.Soc.1991, 113, 7676; Bringmann, G.; Schoner, B.; .1994, 439), which greatly limits people's research on these types of compounds, but in fact these types of compounds have great application value

Method used

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  • Dibenzanthracene, dinaphthopyran and dibenzanthracene, dinaphtho spiropyran analog compound and its preparation
  • Dibenzanthracene, dinaphthopyran and dibenzanthracene, dinaphtho spiropyran analog compound and its preparation
  • Dibenzanthracene, dinaphthopyran and dibenzanthracene, dinaphtho spiropyran analog compound and its preparation

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Experimental program
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Effect test

Embodiment 1

[0029] Synthesis of Compound 1-19:

[0030] In a 100mL three-neck flask equipped with a magnet, add 0.153g (22mmol) lithium, 1.680g (10mmol) dibenzofuran, 3.30mL (22mmol) tetramethylethylenediamine and 50mL dry diethyl ether, and heat to reflux for 24 hours . 0.59 mL (8 mmol) of acetone was added at -78°C, the reaction was gradually raised to room temperature, and stirred overnight. Then slowly add 3N dilute hydrochloric acid for hydrolysis, separate the liquid, add 20mL concentrated hydrochloric acid to the organic phase, stir at room temperature for 2 hours, separate the liquid, and wash the aqueous phase with CH 2 Cl 2 Extract (20mL×4), combine the organic phases, wash with water until neutral, add anhydrous Na 2 SO 4 dry. Remove the solvent with a rotary evaporator, pass through Al 2 o 3 column to obtain 1.23 g of a colorless oily product with a yield of 73%. The synthesis method of compound 2-19 is similar to that of compound 1. Compounds 1-19 1 H NMR, 13 C NMR...

Embodiment 2

[0032] Synthesis of compound 20:

[0033] In a 100mL three-neck flask equipped with a magnet, add 0.153g (22mmol) lithium, 1.680g (10mmol) dibenzofuran, 3.30mL (22mmol) tetramethylethylenediamine and 50mL dry diethyl ether, and heat to reflux for 24 hours . 1.402 g (8 mmol) of 1,3,3-trimethyl-2-indolinone was added at -78°C, the reaction was gradually raised to room temperature, and stirred overnight. Dry the solvent and tetramethylethylenediamine under reduced pressure, then add 50mL of diethyl ether, slowly add 3N dilute hydrochloric acid for hydrolysis, separate the layers, wash the organic phase with 3N dilute hydrochloric acid (20mL×3), combine the aqueous phase, and slowly add NaOH solution to neutral, a large amount of solids precipitated, filtered, and the obtained solids were washed with CH 2 Cl 2 Recrystallized with n-hexane to obtain 2.04 g of light pink crystals. Compound 20 1 H NMR, 13 See Tables 1-4 for CNMR, MS, EA, mp and yield.

Embodiment 3

[0035] Synthesis of compounds 21-32:

[0036] In a 100 mL three-neck flask equipped with a magnet, add 0.153 g (22 mmol) of lithium, 2.680 g (10 mmol) of dinaphthofuran and 50 mL of dry diethyl ether, and stir at room temperature for 24 hours. 0.59 mL (8 mmol) of acetone was added at -78°C, the reaction was gradually raised to room temperature, and stirred overnight. The next day, slowly add 3N dilute hydrochloric acid for hydrolysis, separate the liquid, add 20mL concentrated hydrochloric acid to the organic phase, stir at room temperature for 2 hours, separate the liquid, and wash the aqueous phase with CH 2 Cl 2 Extract (20mL×4), combine the organic phases, wash with water until neutral, add anhydrous Na 2 SO 4 dry. Then the solvent was removed by rotary evaporator, and the 2 o 3 column to obtain 1.79 g of a colorless solid with a yield of 72%. The synthesis method of compound 22-32 is similar to that of compound 21. Compounds 21-32 1 H NMR, 13 C NMR, MS, EA, mp a...

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Abstract

The invention relates to dibenz, naphthopyrans and dibenz and dibenz spiropyran compound, and the method for preparing the same. Said method comprises: dibenzofuran or naphthofurans reacting with lithium with molar ration being 1:2-2.4, opening loop, reacting with aldehyde, ketone, ester or amide at temperature of -70 to -80 Deg. C, the molar ratio between dibenzofuran or naphthofurans and aldehyde, ketone, ester or amide is 1:0.7-1, dewatering and closing loop, and getting final product. The invention is characterized by cheap raw material, simple process, high productivity, and multiple kinds of products.

Description

technical field [0001] The invention relates to a dibenzo, dinaphthopyran and dibenzo, dinaphthospiropyran compound and a preparation method thereof. Background technique [0002] Pyran compounds are a very important class of organic heterocyclic compounds, which are widely used in many fields. Among them, functional group-substituted non-benzopyran compounds are important intermediates in the synthesis of natural products (Danishefsk, S.J.Aldrich.Acta 1986, 19, 59; Schmidt, R.R.Acc.Chem.Res. 1986, 19, 250). Benzo and naphthopyran compounds have received great attention due to their wider practical applications. Benzopyran compounds are a class of biologically active compounds, and there are many reports on the application of this class of compounds in medicine (Evans, J.M.; Stemp, G.Chem.Ber.1991, 27, 439; Attwood, M.R.; Jones, P.S.; Paciorek, P.B.; Redshaw, S. Life Sci. 1991, 48, 803; Attwood, M.R.; 811; Bergmann, R.; Eiermann, V.; Gericke, R. J. Med. Chem. 1990, 33, 27...

Claims

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Application Information

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IPC IPC(8): C07D311/80C07D311/92C07D311/96C07D407/04C07D407/06C07D493/10C07D491/107C07F17/02C09K9/02A61K31/352
Inventor 王佰全王斌李敏雄徐善生
Owner NANKAI UNIV
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