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A kind of synthetic method of 1,2-benzothiazine compounds

A technology for synthesizing benzothiazine and its synthesis method, which is applied in the field of synthesizing 1,2-benzothiazine compounds, can solve the problems of expensive catalyst, unfriendly environment, and small application range of substrates, etc., and shorten the synthetic route and raw material Easy to obtain and mild reaction conditions

Active Publication Date: 2022-07-01
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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  • A kind of synthetic method of 1,2-benzothiazine compounds
  • A kind of synthetic method of 1,2-benzothiazine compounds
  • A kind of synthetic method of 1,2-benzothiazine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017]

[0018] 15.02 mg (0.1 mmol) of S-methyl-S-phenylsulfimide represented by formula I-I, 4.49 mg (0.02 mmol) of palladium acetate, and 15.91 mg (0.2 mmol) of copper oxide were successively added to a 25 mL 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-trimethylsilyl phenyl trifluoromethanesulfonate was stirred at 110 °C for 24 h under an argon-protected airtight system, cooled to room temperature after the reaction, extracted with ethyl acetate, combined with the organic phases, washed with anhydrous Na 2 SO 4 After drying, the ethyl acetate was removed under reduced pressure, and the crude product was separated by column chromatography (using a mixture of petroleum ether and ethyl acetate with a volume ratio of 1:3 as the eluent) to obtain the 5-methyl methacrylate shown in formula V-1. Dibenzo[c,e][1,2]thiazine-5-ox...

Embodiment 2

[0021]

[0022]In this example, the S-methyl-S-phenylidene used in Example 1 was replaced with 4-methoxy-S-methyl-S-phenylsulfimide represented by equimolar formula I-II. Sulfonimine, other steps are the same as in Example 1 to obtain 4-methoxy-5-methyldibenzo[c,e][1,2]thiazine-5-oxide represented by formula V-II , the separation 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, the S-methyl-S-phenyl sulfoxide used in Example 1 was replaced with 4-methyl-S-methyl-S-phenyl sulfoxide represented by 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 represented by formula V-IIII, which The isolated yield was 73%, and the structural characterization data were 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 method for synthesizing 1,2-benzothiazine compounds. Sulfoximine is used as a guiding group, transition metal palladium is used as a catalyst, and in the presence of fluoride, a sulfoximine compound is used. A series of 1,2-benzothiazine compounds were synthesized by cyclization reaction activated by C-H or N-H bonds with aryl alkyne precursors as reaction substrates. The present invention has simple and easy-to-obtain raw materials, mild reaction conditions, realizes the construction of C-C and C-N bonds, shortens the synthesis route, and conforms to the concept of green environmental protection.

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 the combination of a benzene ring and a sulfur-nitrogen heterocycle. It has a wide range of physiological activities and application values. Medicine, pesticides and other fields play an irreplaceable role. Non-steroidal anti-inflammatory drugs (NSAIDs) are widely used as a drug for the treatment of pain and rheumatic diseases (Nature 2002, 420, 860-867), among which 1,2-benzothiazides are a class of non- Steroidal anti-inflammatory drugs, representative drugs are meloxicam and piroxicam, which are clinically found to have a variety of pharmacological activities, such as anti-inflammatory, antibacterial, inhibiting tumor cell proliferation, regulating immune ability, low vascular permeability, etc. ( Ar...

Claims

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Application Information

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Patent Type & Authority Patents(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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