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Preparation method of benzo[e][1,4,3]oxathiazine-1,1-dioxide derivative

A technology of dioxide and derivatives, applied in the direction of electrolytic organic production, electrolytic process, electrolytic components, etc., can solve the problems of low yield, poor universality of synthetic substrates, few reaction selection sites, etc., and achieve high yield , Short response time, green effect after post-processing

Pending Publication Date: 2022-02-18
FUZHOU UNIV
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Problems solved by technology

[0003] At present, the synthesis methods of phenylbenzo[e][1,4,3]oxathiazine-1,1-dioxide derivatives generally have poor universality of synthetic substrates, few reaction sites, and multiple steps are required. Reaction, low yield, multi-step reaction temperature between 120-180 ° C, etc., so it is urgent to develop more efficient, green and environmentally friendly synthetic methods

Method used

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  • Preparation method of benzo[e][1,4,3]oxathiazine-1,1-dioxide derivative
  • Preparation method of benzo[e][1,4,3]oxathiazine-1,1-dioxide derivative
  • Preparation method of benzo[e][1,4,3]oxathiazine-1,1-dioxide derivative

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Effect test

Embodiment 1

[0020] Preparation of 3-phenylbenzo[e][1,4,3]oxathiazine-1,1-dioxide:

[0021]

[0022] At room temperature, add 0.3mmol of N-(benzenesulfonyl)benzamide to a 25mL three-neck flask equipped with carbon cloth as the anode and Pt sheet as the cathode, and then add 0.15mmol of acetic acid and solvent (DCE / HFIP=7:3mL), filled with nitrogen gas to react for 1-5h. After the reaction was completed, 58.3 mg of the target product was obtained through column chromatography purification, with a yield of 75%. The compound is characterized as follows: IR: 1625(m), 1450(w), 1321(s), 1376(s), 1180(s), 808(w), 692(w), 585(m); 1 HNMR (500MHz, Chloroform-d) δ8.25 (dt, J=8.6, 1.6Hz, 2H), 7.80 (dd, J=7.9, 1.6Hz, 1H), 7.72–7.66 (m, 2H), 7.56–7.50 (m,3H),7.44(dd,J=8.5,0.9Hz,1H). 13 C NMR (126MHz, Chloroform-d) δ158.0, 149.3, 134.8, 134.4, 129.5, 129.1, 128.6, 127.9, 124.7, 122.9, 118.1; HRMS (ESI) calculated for C 13 h 10 NO 3 S[M+H + ]: 260.0376; found: 260.0372.

Embodiment 2

[0024] Preparation of 7-methyl-3-phenylbenzo[e][1,4,3]oxathiazine-1,1-dioxide:

[0025]

[0026] At room temperature, add 0.3mmol of N-toluenesulfonylbenzamide to a 25mL three-neck flask equipped with carbon cloth as the anode and Pt sheet as the cathode, and then add 0.15mmol of acetic acid and solvent (DCE / HFIP =7:3mL), filled with nitrogen for 1-5h. After the reaction was completed, 59.0 mg of the target product was obtained through column chromatography purification, with a yield of 72%. The compound is characterized as follows: IR: 1616(m), 1325(s), 1295(m), 1173(m), 820(w), 692(m), 584(m), 554(w); 1 HNMR (500MHz, Chloroform-d) δ8.23(d, J=8.3Hz, 2H), 7.75(s, 1H), 7.65(t, J=7.4Hz, 1H), 7.56–7.50(m, 2H), 7.47(d,J=8.6Hz,1H),7.31(d,J=8.6Hz,1H),2.44(s,3H). 13 C NMR (126MHz, Chloroform-d) δ158.0, 147.2, 138.4, 135.3, 134.6, 129.4, 129.0, 128.7, 124.0, 122.3, 117.8, 21.2; HRMS (ESI) calculated for C 14 h 12 NO 3 S[M+H + ]: 274.0532; found: 274.0524.

Embodiment 3

[0028] Preparation of 7-fluoro-3-phenylbenzo[e][1,4,3]oxathiazine-1,1-dioxide:

[0029]

[0030] At room temperature, add 0.3mmol of N-((4-fluorophenyl)sulfonyl)benzamide to a 25mL three-neck flask equipped with carbon cloth as the anode and Pt sheet as the cathode, and then add 0.15mmol acetic acid and solvent (DCE / HFIP=7:3mL), filled with nitrogen for 1-5h. After the reaction was completed, 35.8 mg of the target product was obtained through column chromatography purification, with a yield of 41%. The compound is characterized as follows: IR: 1614(m), 1573(w), 1325(s), 1301(w), 1171(s), 807(w), 778(w), 787(m), 582( w); 1 H NMR (500MHz, Chloroform-d) δ8.3 (dt, J = 8.6, 1.5Hz, 2H), 7.7–7.6 (m, 2H), 7.6–7.5 (m, 2H), 7.5 (dd, J = 9.2 ,4.1Hz,1H),7.4(m,1H). 13 C NMR (126MHz, Chloroform-d) δ160.1(d, J=252.6H), 158.1, 145.5(d, J=3.0Hz), 135.0, 129.6, 129.2, 128.4, 123.7(d, J=7.7Hz) ,122.3(d,J=24.4Hz),120.4(d,J=8.0Hz),111.1(d,J=26.0Hz); 19 F NMR (471MHz, Chloroform-d) δ-109.2...

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Abstract

The invention discloses a preparation method of a benzo[e][1,4,3]oxathiazine-1,1-dioxide derivative and belongs to the technical field of organic synthesis. According to the method, relatively simple raw materials are used, and the benzoxthiazine derivative is directly synthesized for the first time through an electrochemically promoted smiles rearrangement reaction. According to the scheme, a precious metal catalyst and an oxidizing agent are unnecessary, reaction raw materials are easy to obtain, the yield is high, reaction conditions are mild, reaction time is short, the substrate range is wide, and aftertreatment is simple, convenient and green.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of phenylbenzo[e][1,4,3]oxathiazine-1,1-dioxide derivatives. Background technique [0002] Benzoxathiazine derivatives are a class of widely used intermediates in organic synthesis, and have important application values ​​in natural products, pharmaceutical production, and organic synthesis. Therefore, it is of great application value to study efficient and novel synthetic methods of multi-substituted benzoxathiazine derivatives, and has attracted the attention of researchers in related fields. [0003] At present, the synthesis methods of phenylbenzo[e][1,4,3]oxathiazine-1,1-dioxide derivatives generally have poor universality of synthetic substrates, few reaction sites, and multiple steps are required. Reaction, low yield, multi-step reaction temperature are all between 120-180 ℃, etc., so it is urgent to develop more efficient, green...

Claims

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Application Information

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IPC IPC(8): C25B3/05C25B3/07C25B3/09C25B3/11C25B3/20
CPCC25B3/05C25B3/07C25B3/09C25B3/11C25B3/20
Inventor 叶克印施兆江李楠
Owner FUZHOU UNIV
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