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Synthetic method of benzothiazine formaldehyde derivative

A technology of benzothiazine and synthesis method, which is applied in the field of synthesis of benzothiazine formaldehyde derivatives, can solve the problems of no literature reports, etc., and achieve the effects of simple method, cheap and easy-to-obtain environment, and high regioselectivity

Active Publication Date: 2020-07-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] How to prepare benzothiazine compounds by carbon oxidation of alkynes has not been reported in the literature

Method used

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  • Synthetic method of benzothiazine formaldehyde derivative
  • Synthetic method of benzothiazine formaldehyde derivative
  • Synthetic method of benzothiazine formaldehyde derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] A kind of synthetic method of benzothiazine formaldehyde derivative, comprises the following steps:

[0040] In a 5ml Snaite tube, add benzenesulfonylpropargylamine compound (0.1mmol, 30mg), EosinY (0.002mmol, 1.4mg), potassium carbonate (0.15mmol, 20.7mg), diphenyl disulfide (0.1 mmol, 21.8mg), 1,2-dichloroethane (1mL); the mixture was reacted at room temperature in the air for 24h under 2×30Wblue LEDs, and after the reaction was completed, it was spin-dried and further separated and purified by column chromatography (elution Liquid is a mixed solvent of petroleum ether and ethyl acetate, the volume ratio is 1:1), to obtain 23.5 mg of product (compound 1), and the yield is: 75%.

[0041] Benzenesulfonyl propargylamine compound: R 1 is 4-Me; R 2 For 4-Me. (4-Me represents the position of the methyl group on the benzene ring)

[0042] The structural characterization data of the product obtained in this embodiment are as follows:

[0043] 1 H NMR (400MHz, CDCl 3 ...

Embodiment 2

[0049] The synthetic method of benzothiazine formaldehyde derivative comprises the following steps:

[0050] In a 5ml Snaite tube, add benzenesulfonylpropargylamine compound (0.1mmol, 30mg), EosinY (0.002mmol, 1.4mg), potassium carbonate (0.15mmol, 20.7mg), diphenyl disulfide (0.1 mmol, 21.8mg), 1,2-dichloroethane (1mL); the mixture was reacted at room temperature in the air for 24h under 2×30Wblue LEDs, and after the reaction was completed, it was spin-dried and further separated and purified by column chromatography to obtain the product (Compound 2) 16.3 mg, yield: 51%.

[0051] Benzenesulfonyl propargylamine compound: R 1 is 4-Me; R 2 For 2-Cl. (2-Cl represents the position of Cl on the benzene ring)

[0052] The structural characterization data of the product obtained in this embodiment are as follows:

[0053] 1 H NMR (400MHz, CDCl 3 )δ9.62(s,1H),8.71(s,1H),7.93(d,J=8.1Hz,1H),7.77(d,J=7.7Hz,1H),7.60(d,J=7.9Hz, 1H), 7.55–7.42(m,3H), 7.31(s,1H), 2.55(s,3H). ima...

Embodiment 3

[0059] The synthetic method of benzothiazine formaldehyde derivative comprises the following steps:

[0060] In a 5ml Snaite tube, add benzenesulfonylpropargylamine compound (0.1mmol, 30mg), EosinY (0.002mmol, 1.4mg), potassium carbonate (0.15mmol, 20.7mg), diphenyl disulfide (0.1 mmol, 21.8mg), 1,2-dichloroethane (1mL); the mixture was reacted at room temperature in the air for 24h under 2×30Wblue LEDs, and after the reaction was completed, it was spin-dried and further separated and purified by column chromatography to obtain the product (Compound 3) 22.2 mg, yield: 64%.

[0061] Benzenesulfonyl propargylamine compound: R 1 is 4-Me; R 2 It is 3-Me-4-Cl (representing the meta-position of the methyl group on the benzene ring and the para-position of chlorine on the benzene ring).

[0062] The structural characterization data of the product obtained in this embodiment are as follows:

[0063] 1 H NMR (400MHz, CDCl 3 )δ9.49(s,1H),8.56(s,1H),7.78(d,J=8.2Hz,1H),7.37(d,J=8....

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Abstract

The invention belongs to the technical field of benzothiazide derivatives, and discloses a synthetic method of a benzothiazide formaldehyde derivative. The synthesis method comprises the following steps: in the system of an organic solvent, an alkaline compound, a photocatalyst and an additive, carrying out a reaction on a benzenesulfonyl propargylamine derivative in an aerobic environment throughillumination to obtain a benzothiazine formaldehyde derivative, wherein the additive is more than one of diphenyl disulfide and thiophenol. According to the method, the benzothiazine compound is prepared by utilizing the carbon oxidation reaction of alkyne. The method is simple, convenient, efficient and high in regioselectivity, the used raw materials are simple and easy to obtain, no extra organic oxidizing agent needs to be added, oxygen in the air is used as an oxygen source and is environmentally friendly, cheap and easy to obtain. In addition, the whole operation process is simple and feasible, steps are simple and products are easy to purify.

Description

technical field [0001] The invention relates to the field of synthesis of benzothiazine formaldehyde derivatives, in particular to a synthesis method of benzothiazine formaldehyde derivatives. Background technique [0002] Thiazide compounds are very important molecular frameworks, how to quickly and efficiently construct such molecular frameworks is of great significance in organic synthesis. In recent years, the construction of C-O, C=O, C-X (X=C, N, O, Cl, Br) by using the oxygen functionalization reaction of unsaturated carbon-hydrogen bonds has been developed rapidly, mainly studying the amine oxidation of alkynes, double oxidation , Halogen oxidation, and sulfur oxidation reactions to build complex molecular frameworks. Such as (1) H.Peng, N.-G.Akhmedov, Y.-F.Liang, N.Jiao and X.Shi, Synergistic Gold and Iron dual catalysis: preferred radical addition toward vinyl-gold intermediate over alkene, J.Am .Chem.Soc.,2015,137,8912; (2)T.Miura,T.Biyajima,T.Fujii and M.Muraka...

Claims

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Application Information

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IPC IPC(8): C07D279/02
CPCC07D279/02
Inventor 曾伟陈凤娟
Owner SOUTH CHINA UNIV OF TECH
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