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A 1,4-disulfonylated fully substituted pyrazole compound and its preparation and application

A technology of compounds and pyrazoles, which is applied in 1 field, can solve the problems of less reports on fully substituted pyrazoles, and achieve the effects of high reaction atom economy, improved anti-inflammatory activity, and good application value

Active Publication Date: 2022-05-17
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although a large number of studies and applications on the synthesis of pyrazoles have been carried out in the literature, there are relatively few reports on the synthesis of 1,4-bissulfonylated fully substituted pyrazoles

Method used

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  • A 1,4-disulfonylated fully substituted pyrazole compound and its preparation and application
  • A 1,4-disulfonylated fully substituted pyrazole compound and its preparation and application
  • A 1,4-disulfonylated fully substituted pyrazole compound and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-20

[0060] Example 1-20: Add sulfonylhydrazide (II) (0.5mmol), 1,3-diketone (III) (0.6mmol), sodium sulfinate (IV) (1.0mmol), iodine in a 10mL Schlenk tube Simple substance (0.75mmol), dipotassium hydrogen phosphate trihydrate (0.40mmol) and acetonitrile (4.5mL), tighten the cock, then stir at room temperature (25°C) for 22 hours, add saturated aqueous solution of sodium thiosulfate and stir to precipitate The white solid was filtered, washed with water and petroleum ether successively, the solid was collected and dried to obtain the product.

[0061] The reaction formula is as follows:

[0062]

[0063] Explanation of substituent abbreviation in the following examples:

[0064] -Ts p-toluenesulfonyl CH 3 -C 6 h 5 -SO 2 -

[0065] -Ph phenyl

[0066] -Me methyl

[0067] -n-Pr n-propyl

[0068] -i-Bu isobutyl

[0069] -Et ethyl

[0070] different R 1 , R 2 , R 3 and R 4 The different products obtained are as follows:

Embodiment 1

[0072] 1-([1,1'-Biphenyl]-4-ylsulfonyl)-3,5-dimethyl-4-tosyl-1H-pyrazole (P1)

[0073]

[0074] White solid, 85% yield. Mp162–164°C.

[0075] 1 H NMR (400MHz, CDCl 3 )δ8.04(d,J=8.4Hz,2H),7.79-7.72(m,4H),7.59(d,J=8.0Hz,2H),7.53-7.41(m,3H),7.32(d,J =8.0Hz, 2H), 2.89(s, 3H), 2.42(s, 3H), 2.38(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ151.4,148.1,146.8,144.6,139.2,138.5,135.2,129.9,129.1,129.0,128.7,128.2,127.4,126.7,121.9,21.5,13.7,11.8; HRMS(TOFMS)m / z[M+Na] + calcd for C 24 h 22 N 2 o 4 S 2 Na: 489.0919; Found: 489.0923.

Embodiment 2

[0077] 3,5-Dimethyl-1-(naphthalen-2-ylsulfonyl)-4-tosyl-1H-pyrazole(P2)

[0078]

[0079] White solid, 85% yield. Mp148–150°C.

[0080] 1 H NMR (400MHz, CDCl 3 )δ8.61 (s, 1H), 8.00 (t, J = 9.0Hz, 2H), 7.92 (d, J = 8.0Hz, 2H), 7.83 (dd, J = 8.6, 1.4Hz, 2H), 7.76- 7.62(m, 4H), 7.30(d, J=8.0Hz, 2H), 7.53-7.41(m, 3H), 7.32(d, J=8.0Hz, 2H), 2.91(s, 3H), 2.40(s ,3H),2.36(s,3H); 13 C NMR (100MHz, CDCl 3 )δ151.3, 146.8, 144.5, 139.1, 135.7, 133.6, 131.8, 130.4, 130.1, 130.0, 129.9, 129.6, 128.1, 128.0, 126.6, 122.0, 121.9, 21.5, 13.6, 11.8; HRm / z[TOFMS] +Na] + calcd for C 22 h 20 N 2 o 4 S 2 Na: 463.0762; Found: 463.0765.

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Abstract

The application discloses a 1,4-bissulfonylated fully substituted pyrazole compound and its preparation and application. The sulfonylhydrazine compound, 1,3-dicarbonyl compound and sodium sulfinate compound are combined in a single substance Under the joint action of iodine and alkali, carry out multi-component reaction in solvent, one-pot method prepares 1,3,4,5-tetrasubstituted pyrazole compound of 1,4-disulfonylation, and its general structural formula is : where, R 1 , R 2 , R 4 each independently selected from aryl, heteroaryl or aliphatic, and R 1 and R 4 Different; R 3 is an aliphatic group; the aryl, heteroaryl or aliphatic group is optionally substituted by 1 to 5 substituents. The preparation method of the invention has cheap and easy-to-obtain raw materials, diverse structures, mild reaction conditions, simple post-treatment, and has potential industrialization prospects.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical and chemical intermediates, in particular to a method for preparing 1,4-bissulfonylated fully substituted pyrazole compounds and the prepared 1,4-bissulfonylated fully substituted pyrazole class of compounds. Background technique [0002] Pyrazoles are an important class of five-membered nitrogen heterocyclic compounds with various pharmacological activities, including anti-inflammatory and analgesic, anti-tumor, anti-depressant, anti-convulsant, anti-diabetic and anti-bacterial. Pyrazole can be used as an intermediate of some medicines and pesticides, and occupies a very important position in the research and development of medicines and pesticides. In modern heterocyclic chemistry, the construction of this skeleton has been extensively studied, and a large number of efficient methods for synthesizing such compounds have been established. The sulfonyl group is one of the mos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/18A61P29/00
CPCC07D231/18A61P29/00Y02A50/30
Inventor 况锦强马永敏
Owner TAIZHOU UNIV