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Method for producing benzo thiazides compounds

A technology of benzothiazine and compound, which is applied in the field of preparation of benzothiazine compounds, and achieves the effects of good application prospect, high product yield, and simple reaction operation

Inactive Publication Date: 2008-07-16
FUDAN UNIV
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Problems solved by technology

And the synthesis of isomer I (4-methylene-1H-benzo[d][1,3]thiazine-2(4H)-imine) of benzothiazine compound II and its biological The research on the activity aspect has not been reported so far. Based on the interest in the research of related nitrogen-containing heterocyclic compounds, the present invention proposes a method to obtain 4-methylene-1H-benzo[d][1,3]thiazide efficiently. The method of oxazine-2(4H)-imine skeleton compound

Method used

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  • Method for producing benzo thiazides compounds

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Embodiment 1

[0015] Example 1 2-(2-phenylethynyl)aniline (193.0mg, 1.0mmol), phenylisothiocyanate (405.0mg, 3.0mmol), silver trifluoromethanesulfonate (2.6mg, 0.01mmol) , tetrahydrofuran (2 mL) was stirred at room temperature for about 24 hours. The solvent was evaporated to dryness, water (10 mL) was added, extracted with ethyl acetate (20 mL×2), dried over anhydrous sodium sulfate, concentrated and separated by column chromatography to obtain 321 mg of a colorless substance with a yield of 96%.

[0016] 1 H NMR (400MHz, CDCl 3 )δ7.06(t, J=7.3Hz, 1H), 7.17(s, 1H), 7.19(dd, J=1.5, 7.8Hz, 1H), 7.27-7.40(m, 5H), 7.41-7.45(m , 4H), 7.53-7.58 (m, 3H); 13 C NMR (100MHz, CDCl 3 )δ120.2, 121.7, 123.5, 124.8, 124.9, 125.9, 126.6, 127.1, 127.7, 128.2, 128.9, 129.3, 129.6, 135.6, 139.9, 143.2, 147.6; Ms (EI) m / z 328 (M + ); Elemental analysis calcd(%) for C 21 h 16 N 2 S: C 76.80, H 4.91, N 8.53; Found: C 76.64, H 4.92, N 8.62.

Embodiment 2

[0018] 2-(2-Phenylethynyl)aniline (92.0mg, 0.5mmol), 4-nitro-phenylisothiocyanate (180.0mg, 2.0mmol), silver trifluoromethanesulfonate (6.5mg, 0.025 mmol), tetrahydrofuran (1 mL) was stirred at room temperature for about 18 hours. The solvent was evaporated to dryness, water (10 mL) was added, extracted with ethyl acetate (20 mL×2), dried over anhydrous sodium sulfate, concentrated and separated by column chromatography to obtain 183 mg of a colorless substance with a yield of 98%.

[0019] 1 H NMR (400MHz, DMSO) δ7.18-7.50(m, 10H), 7.65(d, J=7.3Hz, 1H), 8.02(d, J=8.0Hz,, 2H), 8.13(d, J=8.3 Hz, 2H); 13 C NMR (100MHz, DMSO) δ119.2, 121.3, 125.4, 125.8, 126.4, 127.3, 128.3, 128.8, 129.7, 130.4, 135.8, 141.7, 142.9, 146.7, 147.3; Ms (EI) m / z 373 (M + ); Elemental analysis calcd(%) for C 21 h 15 N 3 o 2 S: C 67.54, H 4.05, N 11.25; Found: C 67.82, H 3.98, N 10.97.

Embodiment 3

[0021] 4-Methyl-2-(2-phenylethynyl)aniline (103.6mg, 0.5mmol), phenylisothiocyanate (135.0mg, 1.0mmol), silver trifluoromethanesulfonate (6.5mg, 0.025 mmol), tetrahydrofuran (2 mL) was stirred at room temperature, and TLC tracked and detected that the reaction was complete for 36 hours. The solvent was evaporated to dryness, water (10 mL) was added, extracted with ethyl acetate (20 mL×2), dried, concentrated and separated by column chromatography to obtain 167.6 mg of a colorless substance with a yield of 98%.

[0022] 1 H NMR (400MHz, CDCl 3 )δ2.38(s, 3H), 7.04(t, J=7.3Hz, 1H), 7.13-7.17(m, 3H), 7.27-7.33(m, 3H), 7.35(s, 1H), 7.38-7.43 (m, 4H), 7.53 (d, J=8.3Hz, 2H); 13 C NMR (100MHz, CDCl 3 )δ20.5, 119.5, 120.8, 122.8, 124.5, 125.3, 126.1, 126.3, 127.0, 127.6, 128.4, 128.8, 130.0, 133.9, 135.2, 139.4, 140.4, 146.4; Ms(EI) m / z 328(M + );Elemental analysis calcd(%)forC 21 h 16 N 2 S: C 76.80, H 4.91, N 8.53; Found: C 76.65, H 4.90, N 8.35.

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Abstract

The invention belongs to the technical field of organic chemistry, in particular to a benzothiazole compounds and a preparation method for the compounds. The structures of the compounds are attributed and determined by the methods like <1>H NMR, <13>CNMR, IR, MS, elementary analysis, and a single-crystal X-ray diffraction, etc. The invention uses a silver triflate as a catalyst to prepare 4-methylene-1H-benzo[d] [1, 3] thiazine-2(4H)-imine framework compounds by mixing an ortho-alkynyl aniline and an isothiocyanate in a tetrahydrofuran to react at a room temperature. The method of the invention has the advantages of mild reaction condition, simple operation, lower cost, fewer side effects and high purity of the product; thereby having a great application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of benzothiazine compounds. Background technique [0002] 1,4-benzothiazine compounds have been widely studied because of their biological anti-inflammatory and other activities (J.Med.Chem.1973,16,780), while 3,1-benzothiazine compounds The research on the synthesis method of II and its biological activity has also been reported (Miller, B.L.Org.Lett. 1997, 62, 1106; Schmidt, R.R.J. Heterocycl. Chem. 1999, 36, 153; Ress, C.W. Synlett 1997, 704; Pazdera, P. Molecules 2000, 7, 96; Schmittel M. Synthesis 2004, 3, 415). And the synthesis of isomer I (4-methylene-1H-benzo[d][1,3]thiazine-2(4H)-imine) of benzothiazine compound II and its biological The research on the activity aspect has not been reported so far. Based on the interest in the research of related nitrogen-containing heterocyclic compounds, the present invention proposes a met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/08
Inventor 丁秋平吴劼
Owner FUDAN UNIV
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