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Synthetic method of 2,3-dihydro-[1,4]-benzothiazine compound

A technology of benzothiazine and synthesis method, which is applied in the field of organic compound process application, can solve the problems of difficult preparation of o-aminothiophenol, insufficient substrate adaptability, easy oxidation, etc., and achieve low cost and high yield , the effect of less pollution

Inactive Publication Date: 2013-05-15
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in this method, the preparation of substituted o-aminothiophenol is difficult, and the adaptability of the substrate is not wide enough. Not only the taste is large, the pollution is serious, and it is easy to be oxidized, so the application of this method is restricted.

Method used

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  • Synthetic method of 2,3-dihydro-[1,4]-benzothiazine compound
  • Synthetic method of 2,3-dihydro-[1,4]-benzothiazine compound
  • Synthetic method of 2,3-dihydro-[1,4]-benzothiazine compound

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Experimental program
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Effect test

Embodiment 1

[0021] Synthesis of 4-tosyl-2,3-dihydro-[1,4]-benzothiazine:

[0022]

[0023] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. Substrate 1aa (0.1 mmol, 52.8 mg), PdCl 2 (dppf) (0.01mmol, 7.3mg), Cs 2 CO 3 (0.3mmol, 98mg), Na 2 S 2 o 3 (0.5mmol, 124mg) were successively weighed into the reaction tube, evacuated for nitrogen, and MeCN (2mL) was added under nitrogen atmosphere. The reaction system was heated to 150°C and reacted for 8 hours. After the TCL detection reaction was completed, the system was cooled to room temperature. Silica gel was directly added, and spin-dried column chromatography gave white solid 2a (10%). R f = 0.7 (ethyl acetate: petroleum ether = 5: 1); 1 H NMR (400MHz, CDCl 3 ): δ2.39(s, 3H), 2.86(t, J=5.6Hz, 2H), 3.97(t, J=6.0Hz, 2H), 7.03-7.10(m, 2H), 7.19(d, J= 8.4Hz, 2H), 7.46(d, J=8.4Hz, 2H), 7.65-7.68(m, 1H); 13 C NMR (100MHz, CDCl 3 ): δ143.9, 137.2, 134.2, 129.7, 128.0, 127.9, 127.0, 126.7, 126.4, 124.5, 44.5, 2...

Embodiment 2

[0025]Synthesis of 4-tosyl-2,3-dihydro-[1,4]-benzothiazine:

[0026]

[0027] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. Substrate 1aa (0.1 mmol, 52.8 mg), PdCl 2 (dppf) (0.01mmol, 7.3mg), Cs 2 CO 3 (0.3mmol, 98mg), Na 2 S 2 o 3 (0.5mmol, 124mg) were weighed into the reaction tube in turn, evacuated for nitrogen, and added MeCN (2mL) and H 2 O (200 μL). The reaction system was heated to 150°C and reacted for 8 hours. After the TCL detection reaction was completed, the system was cooled to room temperature. Silica gel was directly added, and spin-dried column chromatography gave white solid 2a with a yield of 15%. Analysis data is with embodiment 1.

Embodiment 3

[0029] Synthesis of 4-tosyl-2,3-dihydro-11,4]-benzothiazine:

[0030]

[0031] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. Substrate 1aa (0.1 mmol, 52.8 mg), PdCl 2 (dppf) (0.01mmol, 7.3mg), Cs 2 CO 3 (0.3mmol, 98mg), Na 2 S 2 o 3 (0.5mmol, 124mg), TBAB (0.03mmol, 9.7mg), were weighed into the reaction tube in turn, evacuated for nitrogen, and added MeCN (2mL) and H 2 O (200 μL). The reaction system was heated to 150°C and reacted for 8 hours. After the TCL detection reaction was completed, the system was cooled to room temperature. Silica gel was directly added, and spin-dried column chromatography gave white solid 2a with a yield of 39%. Analysis data is with embodiment 1.

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Abstract

The invention discloses a synthetic method of 2,3-dihydro-[1,4]-benzothiazine compound. The method comprises the steps of: by taking 2-iodine-N-(2-iodoethyl) aniline derivant as a reaction material and taking Na2S2O3 as a vulcanization reagent, reacting in a reaction solvent in the presence of a metal palladium catalyst to obtain multisubstituted 2,3-dihydro-[1,4]-benzothiazine compound. The synthetic method is mild in reaction condition, available in material, cheap in material, simple to react and operate and high in yield, provides a key skeleton structure for synthesis of a plurality of natural products and medicines, and can be widely applied to industrial mass production.

Description

technical field [0001] The invention specifically relates to a synthesis method for preparing 2,3-dihydro-[1,4]-benzothiazine compounds, which belongs to the technical field of organic compound technology application. Background technique [0002] 2,3-dihydro-[1,4]-benzothiazine compounds are a very important class of pharmaceutical and chemical intermediates with very high application value. Many drugs and biologically active molecules, such as rufloxacin, DHBT-NE-1, MX-68, HeronamycinA, etc., have a skeleton of 2,3-dihydro-[1,4]-benzothiazine, as follows Shown: [0003] [0004] The traditional method of synthesizing 2,3-dihydro-[1,4]-benzothiazine compounds is mainly through the preparation of o-aminothiophenol compounds. However, in this method, the preparation of substituted o-aminothiophenol is difficult, and the adaptability of the substrate is not wide enough. Not only does it have a strong taste, it is seriously polluted, and it is easily oxidized, which restri...

Claims

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Application Information

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IPC IPC(8): C07D279/16C07D417/04C07D281/10C07D333/54C07D335/06
Inventor 姜雪峰刘会乔宗君
Owner EAST CHINA NORMAL UNIVERSITY
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