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Indole spirooxazine heterocyclic compound and preparation method thereof

A technology for compounds and heterocycles, applied in the field of indolespirooxazine heterocycles and their preparation, can solve problems such as uncommon methods, and achieve the effects of good greening, moderate product yield, and simple reaction operation

Active Publication Date: 2022-07-12
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above methods provide many alternative approaches for the synthesis of indole spiro or nitrogen-containing heterocyclic compounds. The method is indeed uncommon, and there is currently no effective method to obtain such compounds

Method used

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  • Indole spirooxazine heterocyclic compound and preparation method thereof
  • Indole spirooxazine heterocyclic compound and preparation method thereof
  • Indole spirooxazine heterocyclic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] In a 25mL Schlenk reaction tube equipped with a magnetic stirrer, add catalyst Rh 2 (esp) 2 (0.01mmol, 0.02equiv.), N-(3-diazo-1-methylindoline-2-ylidene)-4-methylbenzenesulfonamide (1.5mmol, 3.0equiv), benzisoxazole (0.5 mmol, 1.0 equiv.) and dichloromethane (5 mL) under nitrogen. The reaction solution was placed in an oil bath at 60° C. to react for about 2 to 4 hours. TLC detected that the reaction was complete, and then the reaction solution was cooled to room temperature. During the post-treatment, the catalyst was first removed by suction filtration through a sand core funnel equipped with silica gel, and the obtained filtrate was separated by flash column chromatography to obtain a pure product, 4-methyl-N-(1'-methylspiro[benzo[e]]. [1,3]oxazine-2,3'-indoline]-2'-methylene)benzenesulfonamide. Yield: 74%. The following is the NMR experimental data of product 3a:

[0027] 1H NMR (400MHz, DMSO) δ: 8.50 (s, 1H), 7.69 (d, J=8.2 Hz, 2H), 7.53 (d, J=6....

Embodiment 2

[0030]

[0031] In a 25mL Schlenk reaction tube equipped with a magnetic stirrer, add catalyst Rh 2 (esp) 2 (0.01mmol, 0.02equiv.), N-(3-diazo-1-methylindoline-2-ylidene)-4-methylbenzenesulfonamide (1.5mmol, 3.0equiv), 5-methyl benzazole (0.5 mmol, 1.0 equiv.) and dichloromethane (5 mL) under nitrogen. The reaction solution was placed in an oil bath at 60° C. to react for about 2 to 4 hours. TLC detected that the reaction was complete, and then the reaction solution was cooled to room temperature. During post-treatment, the catalyst was first removed by suction filtration through a sand core funnel equipped with silica gel, and the obtained filtrate was separated by flash column chromatography to obtain a pure product N-(1',6-dimethylspiro[benzo[e][1] ,3]oxazine-2,3'-indoline]-2'-methylene)-4-methylbenzenesulfonamide. Yield: 58%. The following is the NMR experimental data of product 3b:

[0032] 1 H NMR (400MHz, DMSO) δ: 8.44 (s, 1H), 7.69 (d, J=8.2 Hz, 2H), 7.46 (t, ...

Embodiment 3

[0035]

[0036] In a 25mL Schlenk reaction tube equipped with a magnetic stirrer, add catalyst Rh 2 (esp) 2 (0.01mmol, 0.02equiv.), N-(3-diazo-1-methylindoline-2-ylidene)-4-methylbenzenesulfonamide (1.5mmol, 3.0equiv), 5-chloro Benzoxazole (0.5 mmol, 1.0 equiv.) and dichloromethane (5 mL) under nitrogen. The reaction solution was placed in an oil bath at 60° C. to react for about 2 to 4 hours. TLC detected that the reaction was complete, and then the reaction solution was cooled to room temperature. During the post-treatment, the catalyst was first removed by suction filtration through a sand core funnel equipped with silica gel, and the obtained filtrate was separated by flash column chromatography to obtain a pure product N-(6-chloro-1'-methylspiro[benzo[e][ 1,3]oxazine-2,3'-indoline]-2'-methylene)-4-methylbenzenesulfonamide. Yield: 52%. The following is the NMR experimental data of product 3c:

[0037] 1 H NMR (400MHz, DMSO) δ: 8.49 (s, 1H), 7.72–7.66 (m, 3H), 7.53...

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Abstract

The invention provides a novel indole spirooxazine heterocyclic compound and a preparation method thereof. In the method, indole diazo compound and benzisoxazole are used as reaction substrates to react under the catalysis of transition metal, and indole spiro oxazine heterocyclic compounds are prepared with high efficiency through one-step reaction. The indole spiroheterocyclic compounds obtained by this method have potential medicinal activities, and the product molecules contain halogens, carbonimide double bonds and sulfonyl groups, which are prone to various additional transformations, thereby preparing compounds containing more complex structures. Organic compounds of the indole ring system. The method has easy to obtain raw materials, simple reaction system, good chemical selectivity, no need for strict anhydrous and oxygen-free conditions, strong operability, and the ten-gram scale which is easy to enlarge does not obviously affect the yield of the reaction. The functional group of the reaction has good compatibility, wide substrate applicability, stable product, easy separation and purification, suitable for industrial scale-up preparation, and has good application potential.

Description

technical field [0001] The present invention relates to derivatives of indole skeleton, in particular to indole spirooxazine heterocyclic compounds and a preparation method thereof. Background technique [0002] Indole spiro compounds exist in natural products and biologically active drug molecules, and these nitrogen-containing heterocyclic skeletons have significant biological activities in pharmaceutical research due to their spiro quaternary carbon centers: (a)Lin , H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36. (b) Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qiu, S.; .; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P.P.; Tomita, Y.; Parrish, D.A.; Deschamps, J.R.; c) C.V.Galliford, K.A.Scheidt, Angew.Chem.Int.Ed., 2007, 46, 8748. (d) Y.C.Lee, S.Patil, C.Golz, C.Strohmann, S.Ziegler, K.Kumar and H . Waldmann, Nat. Commun., 2017, 8, 14043. (e) Shangary, S.; Qin, D.; McEachern, D.; Liu, M.; Miller, R.S.; Qiu, S.; Nikolovska-Coleska, Z.; Ding, K.; Wang, G.; Che...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/10
CPCC07D498/10C07B2200/13C07B2200/07Y02A50/30
Inventor 陈知远韩翠芬袁建军
Owner JIANGXI NORMAL UNIV
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