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Synthesis method of 1, 2-benzothiazine compound

A technology for synthesizing benzothiazine and its synthesis method, which is applied in the field of synthesizing 1,2-benzothiazine compounds, which can solve the problems of unfriendly environment, small scope of application of substrates, expensive catalysts, etc., and shorten the synthesis route and reaction The effect of mild conditions and easy access to raw materials

Active Publication Date: 2020-01-17
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis methods of these benzothiazine compounds are all intramolecular cyclization reactions, and there are some disadvantages to varying degrees: the need for pre-functionalization, especially halogenated substrates, the scope of substrates is small, the catalyst is expensive, and the environment is not friendly.

Method used

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  • Synthesis method of 1, 2-benzothiazine compound
  • Synthesis method of 1, 2-benzothiazine compound
  • Synthesis method of 1, 2-benzothiazine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017]

[0018] Add 15.02mg (0.1mmol) of S-methyl-S-phenylsulfoximine shown in formula I-I, 4.49mg (0.02mmol) of palladium acetate, and 15.91mg (0.2mmol) of copper oxide in a 25mL pressure-resistant tube , 18.21mg (0.1mmol) 1-adamantanecarboxylic acid, 60.60mg (0.4mmol) cesium fluoride, 19.15mg (0.1mmol) cesium acetate, 2mL dioxane, 59.60mg (0.2mmol) shown in formula II-I 2-trimethylsilylphenyl trifluoromethanesulfonate, stirred at 110°C for 24h in a closed system protected by argon, cooled to room temperature after the reaction, extracted with ethyl acetate, combined the organic phases, and washed with anhydrous Na 2 SO 4 Drying, removal of ethyl acetate under reduced pressure, the crude product was separated by column chromatography (with a mixture of petroleum ether and ethyl acetate volume ratio of 1:3 as the eluent), to obtain 5-methanol shown in formula V-1 Dibenzo[c,e][1,2]thiazine-5-oxide, the isolated yield is 72%, and the structural characterization data are as ...

Embodiment 2

[0021]

[0022]In this example, replace the S-methyl-S-phenyl sulfoximine used in Example 1 with 4-methoxy-S-methyl-S-phenyl sulfoximine shown in equimolar formula I-II Sulfoximine, other steps are identical with embodiment 1, obtain the 4-methoxy-5-methyldibenzo [c, e] [1,2] thiazine-5-oxide compound shown in formula V-II , the isolated yield is 74%, and the structural characterization data are as follows:

[0023] 1 H NMR (600MHz, CDCl 3 )δ7.92(d, J=8.1Hz, 1H), 7.84(d, J=8.8Hz, 1H), 7.56(d, J=2.1Hz, 1H), 7.37(t, J=8.2Hz, 1H) ,7.23(d,J=8.1Hz,1H),7.10(d,J=8.7Hz,1H),7.05(t,J=7.0Hz,1H),3.96(s,3H),3.45(s,3H) ; 13 C NMR (151MHz, CDCl 3 )δ163.00, 143.45, 136.52, 130.84, 126.33, 124.82, 123.51, 120.54, 117.58, 117.15, 115.43, 106.92, 55.71, 45.57; HRMS (ESI) m / z: C 14 h 13 NOS[M+Na] + The theoretical value is 282.0599, and the measured value is 282.0560.

Embodiment 3

[0025]

[0026] In this example, replace the S-methyl-S-phenyl sulfoxide used in Example 1 with 4-methyl-S-methyl-S-phenyl sulfoximine shown in equimolar formula I-III imine, other steps are the same as in Example 1 to obtain 4-methyl-5-methyldibenzo[c,e][1,2]thiazine-5-oxide shown in formula V-IIII, which The isolated yield is 73%, and the structural characterization data are as follows:

[0027] 1 H NMR (600MHz, CDCl 3 )δ8.01-7.97(m,2H),7.80(d,J=8.1Hz,1H),7.39-7.35(m,2H),7.24(d,J=7.9Hz,1H),7.07(t,J =7.5Hz,1H),3.49(s,3H),2.54(s,3H); 13 C NMR (151MHz, CDCl 3 )δ142.64, 142.05, 133.06, 129.56, 127.99, 123.77, 122.99, 122.87, 122.44, 121.27, 119.66, 116.31, 76.24, 76.03, 75.82, 43.98, 21.12; HRMS (ESI) m / z 14 h 13 NOS[M+Na] + The theoretical value is 266.0610, and the measured value is 266.0612.

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Abstract

The invention discloses a synthesis method of 1, 2-benzothiazine compound. According to the synthesis method of the 1, 2-benzothiazine compound, sulfoximine is used as a guide group, transition metalpalladium is used as a catalyst, the sulfoximine compound and an aryne precursor are used as reaction substrates in the presence of fluoride, and a series of 1, 2-benzothiazine compounds are synthesized through cyclization reaction activated by C-H or N-H bonds. The method has the advantages of simple and accessible raw materials and mild reaction conditions, implements the construction of C-C andC-N bonds, shortens the synthesis route, and conforms to the concept of environment friendliness.

Description

technical field [0001] The invention relates to a method for synthesizing 1,2-benzothiazine compounds. Background technique [0002] Heterocyclic compounds occupy an important position in organic chemistry. Benzothiazine refers to a class of heterocyclic compounds formed by combining benzene rings and sulfur nitrogen heterocycles. It has a wide range of physiological activities and application values. Pharmaceuticals, pesticides and other fields play an irreplaceable role. Non-steroidal anti-inflammatory drugs are widely used as a drug for pain and rheumatic diseases (Nature 2002, 420, 860-867), among which 1,2-benzothiazine drugs are a class of non-steroidal anti-inflammatory Steroidal anti-inflammatory drugs, representative drugs are meloxicam and piroxicam, clinically found that these drugs have a variety of pharmacological activities, such as anti-inflammatory, antibacterial, inhibition of tumor cell proliferation, immune regulation, low vascular permeability, etc. ( A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/02C07D513/04
CPCC07D279/02C07D513/04
Inventor 李靖李珊刘莲生魏俊发
Owner SHAANXI NORMAL UNIV
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