1-sulfonamido tetrahydrocarbazole compound as well as synthesis method and application thereof

A technology of sulfonamidotetrahydrocarbazoles and tetrahydrocarbazoles, which is applied in the field of synthesis of organic compounds to achieve the effects of good atom economy, easy availability of raw materials, great use value and social and economic benefits

Inactive Publication Date: 2018-08-24
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no related technology for the

Method used

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  • 1-sulfonamido tetrahydrocarbazole compound as well as synthesis method and application thereof
  • 1-sulfonamido tetrahydrocarbazole compound as well as synthesis method and application thereof
  • 1-sulfonamido tetrahydrocarbazole compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Synthesis of N-(9-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzenesulfonamide (1a)

[0029]

[0030] 9-methyl-2,3,4,9-tetrahydro-1H-carbazole (170mg, 0.5mmol), chloramine B (235mg, 1.1mmol), iodine (13mg, 0.05mmol) and 1,4- Dioxane (3mL) was successively added into a 25mL Schlenk bottle, and reacted at room temperature for 9 hours. After the reaction was completed, the organic solvent was removed under reduced pressure, eluted with petroleum ether / ethyl acetate, and separated by a silica gel column to obtain N-( 9-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzenesulfonamide (1a) 144mg, yield 85%. 1 H NMR (400MHz, DMSO-d6) δ8.14 (dd, J = 8.2, 2.6Hz, 1H), 7.98–7.79 (m, 2H), 7.64 (tdd, J = 9.5, 4.9, 2.2Hz, 3H), 7.37(ddd, J=22.7,8.2,2.5Hz,2H),7.19–7.05(m,1H),6.97(td,J=7.4,2.4Hz,1H),4.68(dd,J=8.2,3.5Hz, 1H),3.44(s,3H),2.73–2.56(m,1H),2.45–2.33(m,1H),1.89–1.71(m,1H),1.67–1.50(m,3H). 13 C NMR (101MHz, DMSO-d6) δ142.93, 137.22, 132.97, 132.90, 129.72, 126.78...

Embodiment 2

[0031] Example 2: Synthesis of N-(9-benzyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzenesulfonamide (1b)

[0032]

[0033] 9-benzyl-2,3,4,9-tetrahydro-1H-carbazole (208mg, 0.5mmol), chloramine B (235mg, 1.1mmol), iodine (13mg, 0.05mmol) and 1,4- Dioxane (3mL) was successively added into a 25mL Schlenk bottle, and reacted at room temperature for 9 hours. After the reaction was completed, the organic solvent was removed under reduced pressure, eluted with petroleum ether / ethyl acetate, and separated by a silica gel column to obtain N-( 9-benzyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzenesulfonamide (1b) 182mg, yield 87%. 1 H NMR (400MHz, CDCl 3 )δ7.82(d,J=7.7Hz,2H),7.66–7.38(m,4H),7.29–7.04(m,6H),6.89–6.72(m,2H),5.17(d,J=2.8Hz ,2H),4.78(d,J=8.6Hz,1H),4.66(d,J=8.4Hz,1H),2.96–2.77(m,1H),2.61(dd,J=10.6,4.9Hz,1H) ,1.93–1.64(m,4H). 13 C NMR (101MHz, CDCl 3)δ141.37,137.92,137.12,132.71,131.48,129.22,128.61,127.14,126.86,126.37,125.88,122.73,119.35,118.80,113.64,109.91,46.09,45.8...

Embodiment 3

[0034] Example 3: Synthesis of N-(6,9-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzenesulfonamide (1c)

[0035]

[0036] 6,9-Dimethyl-2,3,4,9-tetrahydro-1H-carbazole (177mg, 0.5mmol), chloramine B (235mg, 1.1mmol), iodine (13mg, 0.05mmol) and 1 , 4-dioxane (3mL) was sequentially added to a 25mL Schlenk bottle, and reacted at room temperature for 9 hours. After the reaction, the organic solvent was removed under reduced pressure, eluted with petroleum ether / ethyl acetate, and separated by silica gel column to obtain N-(6,9-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzenesulfonamide (1c) 128mg, yield 72%. 1 H NMR (400MHz, CDCl 3 )δ8.04–7.90(m,2H),7.71–7.44(m,3H),7.26(dd,J=2.2,1.2Hz,1H),7.13(dd,J=8.3,1.5Hz,1H),7.05 (d,J=8.4Hz,1H),4.85–4.60(m,2H),3.48(t,J=1.2Hz,3H),2.85–2.70(m,1H),2.57–2.36(m,4H), 1.89–1.60(m,4H). 13 C NMR (101MHz, CDCl 3 )δ141.74,135.76,132.75,131.61,129.25,128.26,126.87,126.19,123.97,118.35,112.31,108.79,46.12,30.21,29.10,21.40,20.62,17.95.cal 2...

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Abstract

The invention discloses a 1-sulfonamido tetrahydrocarbazole compound and a synthesis method thereof. The synthesis method is characterized by taking a tetrahydrocarbazole derivative as a raw material,taking iodine salt as a catalyst, taking chloramine salt as an oxidant and reacting in an organic solvent under room temperature to synthesize a series of 1-sulfonamido tetrahydrocarbazole compounds;a reaction formula is as shown in the description. The method has the advantages of simple steps, mild conditions, high atom economy, environment friendliness and the like; the method is simple and efficient; the raw materials are easily available; the 1-sulfonamido tetrahydrocarbazole compound is of an important excellent framework structure, thus can be widely used in the fields of organic synthesis and pharmaceutical chemistry, and has high usage value and good social and economic benefits; the 1-sulfonamido tetrahydrocarbazole compound is an important key intermediate for synthesizing bioactive molecules and active natural products, and can be extremely widely used in the field of organic synthesis.

Description

technical field [0001] The present invention relates to the synthesis of organic compounds, in particular to a 1-sulfonamide tetrahydrocarbazole compound and its synthesis method, and the use of the 1-sulfonamide tetrahydrocarbazole compound as a raw material in organic synthesis application. Background technique [0002] 1-Sulfonamide tetrahydrocarbazole compounds are an important class of dominant skeletons, which are commonly found in drug molecules, natural products and synthetic compounds. The study found that the compound of this structural unit has anti-HPV activity, NPY receptor antagonist, and PGD 2 Receptor antagonist activity. So far, there is no related technology to synthesize 1-sulfonamidotetrahydrocarbazole compounds. [See: (1) Boggs, S.D. et al. Org. Process Res. Dev. 2007, 11, 539. (2) Gud-mundsson, K. S. et al. Bioorg. Med. Chem. Lett. 2009, 19, 3489. (3 ) Gudmundsson, K.S.etal.Bioorg.Med.Chem.Lett.2009,19,4110. (4)Fabio,R.D.etal.Bioorg.Med.Chem.Lett.20...

Claims

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Application Information

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IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 刘小卒周宇翔刘培均
Owner ZUNYI MEDICAL UNIVERSITY
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