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A kind of preparation method of 1,2,4-benzothiadiazine series compound

A technology of benzothiadiazines and compounds, which is applied in the field of preparation of 1,2,4-benzothiadiazines compounds, and achieves good application prospects, short reaction time and high chemoselectivity

Active Publication Date: 2019-07-16
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, after literature research, we found that there is no effective method for the one-step synthesis of 1,2,4-benzothiadiazines

Method used

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  • A kind of preparation method of 1,2,4-benzothiadiazine series compound
  • A kind of preparation method of 1,2,4-benzothiadiazine series compound
  • A kind of preparation method of 1,2,4-benzothiadiazine series compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] Dissolve the catalyst-carbonylcyclopentadiene cobalt iodide (9.2mg, 0.01mmol) silver bistrifluoromethanesulfonimide (16mg, 0.02mmol) in the mixed solvent tert-amyl alcohol / chloroform (1.0 mL, v:v=1:1), heated to 110°C in Biotage microwave reactor, then added dropwise reactant diphenylsulfinimide (43.4mg, 0.2mmol) and 3-phenyl-1, 4,2-Oxadiazol-5-one (64mg, 0.4mmol) and mixed solvent (1.0mL) were added to the reaction system, and the reaction was continued for 2 hours under air atmosphere, and the reaction was complete by TLC detection. During the post-treatment, the catalyst is removed by suction filtration through a sand core funnel equipped with silica gel, and the obtained filtrate is separated by flash column chromatography to obtain the pure product 1,3-diphenylbenzo[e][1,2,4]thiophene Oxadiazole 1-oxygen compound 3a. Yield: 85%. The following is the NMR experimental data of product 3a:

[0025] 1 H NMR (400MHz, CDCl 3 )δ:8.47-8.40(m,2H),7.88(dd,J=5...

Embodiment 2

[0028]

[0029] Dissolve the catalyst-carbonylcyclopentadiene cobalt iodide (230mg, 0.25mmol) silver bistrifluoromethanesulfonimide (400mg, 0.5mmol) in the mixed solvent tert-amyl alcohol / chloroform (25mL, v:v=1:1), heated to 110°C in Biotage microwave reactor, then added dropwise reactant diphenylsulfinimide (1.09g, 5.0mmol) and 3-phenyl-1,4, 2-Oxadiazol-5-one (1.6 g, 10 mmol) was added to the reaction system, and the reaction was continued for 3 hours under an air atmosphere, and the reaction was complete as detected by TLC. During the post-treatment, the catalyst is removed by suction filtration through a sand core funnel equipped with silica gel, and the obtained filtrate is separated by flash column chromatography to obtain the pure product 1,3-diphenylbenzo[e][1,2,4]thiophene Oxadiazole 1-oxygen compound 3a. Yield: 80%. The following is the NMR experimental data of product 3a:

[0030] 1 H NMR (400MHz, CDCl 3 )δ:8.47-8.40(m,2H),7.88(dd,J=5.4Hz,3.6Hz,2H),7.70-7.54...

Embodiment 3

[0033]

[0034] Dissolve the catalyst-carbonylcyclopentadiene cobalt iodide (230mg, 0.25mmol) silver bistrifluoromethanesulfonimide (400mg, 0.5mmol) in the mixed solvent tert-amyl alcohol / chloroform (25mL, v:v=1:1), heated to 120°C in an oil bath reactor, then added dropwise the reactant diphenylsulfinimide (1.09g, 5.0mmol) and 3-phenyl-1,4 , 2-oxadiazol-5-one (1.6 g, 10 mmol) was added to the reaction system, and the reaction was continued for 16 hours under air atmosphere, and the reaction was complete by TLC detection. During the post-treatment, the catalyst is removed by suction filtration through a sand core funnel equipped with silica gel, and the obtained filtrate is separated by flash column chromatography to obtain the pure product 1,3-diphenylbenzo[e][1,2,4]thiophene Oxadiazole 1-oxygen compound 3a. Yield: 69%. The following is the NMR experimental data of product 3a:

[0035] 1 H NMR (400MHz, CDCl 3 )δ:8.47-8.40(m,2H),7.88(dd,J=5.4Hz,3.6Hz,2H),7.70-7.54(m,5H...

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Abstract

A preparation method of 1,2,4-benzothiadiazine series compounds, the method adopts sulfoxide sulfonylimide and 3-aryl (alkyl) base-1,4,2-oxadiazol-5-ketone as The reaction substrate, under the co-catalysis of transition metal catalyst and co-catalyst, is heated by microwave reactor (reaction temperature is 100-120°C, reaction time is 2-3 hours) or heated by oil bath (reaction temperature is 110-130°C ℃, the reaction time is 15~18 hours) to react under the conditions of C-H / N-H bond to form a heterocyclic compound containing benzosulfoxide and dinitrogen, that is, to obtain 1,2,4 ‑Benzothiadiazine series compounds. The by-products obtained by this method are only carbon dioxide and water, which is convenient for separation and purification; the chemical selectivity of the reaction is high, and the substrate has wide applicability; no additional inert gas protection is required as the reaction environment, which is convenient and simple to operate; the reaction time under microwave conditions is short , with extremely low cost and few by-products, and can be applied to large-scale preparation.

Description

technical field [0001] The invention relates to a derivative of a sulfur-containing and diazaheterocyclic drug skeleton, in particular to a preparation method of 1,2,4-benzothiadiazine compounds. Background technique [0002] Sulfoxide sulfonylimides are an important class of organic molecules with biological activity. As early as the 1970s, diphenylsulfoximine (diphenylsulfoximine) was used as a pharmacophore for clinical drug development research. At present, drugs containing such sulfoxide sulfonylimide skeletons and successfully marketed for clinical application include: Suloxifen (suloxifen), a drug for treating wheezing and asthma; HE-HK 52, a drug for relieving spasms[ (a) Satzinger, G. Drug News Perspect.2001, 14, 197. (b) Pothmann, R. Drugs Future 1982, 7, 478.]; insect repellant Sulfoxaflor (sulfoxaflor); antiallergic drug Sudexanox (RU 31156 , Sudiguno); pan-CDK inhibitor ZK 304709 dependent on cyclin (CDKs) activating enzymes [G.Siemeister, U.Luecking, C.Wagner...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/24C07D417/04
CPCC07D285/24C07D417/04
Inventor 陈知远黄家翩彭以元
Owner JIANGXI NORMAL UNIV
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