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3-aryl-6-aralkyl-1, 4, 5, 6-tetrahydropyridazine compound and preparation method and application thereof

A tetrahydropyridazine and compound technology, which is applied in the field of nitrogen-containing heterocyclic compounds, can solve the problems of large limitation of substrates and troublesome post-processing, and achieves the effects of short synthesis route, simple post-processing and good application value.

Active Publication Date: 2021-06-08
江苏冠瑜生物科技有限公司
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  • Claims
  • Application Information

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Problems solved by technology

[0008] However, these two methods have the disadvantages of large substrate limitation and troublesome post-processing.

Method used

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  • 3-aryl-6-aralkyl-1, 4, 5, 6-tetrahydropyridazine compound and preparation method and application thereof
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  • 3-aryl-6-aralkyl-1, 4, 5, 6-tetrahydropyridazine compound and preparation method and application thereof

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[0076] The present invention also provides a preparation method of 3-aryl-6-aralkyl-1,4,5,6-tetrahydropyridazine compounds, comprising the following steps:

[0077] 1) After mixing and reacting the compound having the structure of formula II, arylsulfonyl hydrazide and the first solvent, the compound having the structure of formula III is obtained;

[0078] 2) Under the conditions of an airtight and protective atmosphere, after the compound with the structure of formula III obtained in the above steps, the base, the catalyst and the second solvent are subjected to a photocatalytic reaction, the 3-aryl- 6-aralkyl-1,4,5,6-tetrahydropyridazines;

[0079]

[0080] Among them, R 1 , R 2 each selected from H, CH 3 ;

[0081] R 3 selected from CH 3 ; 4 selected from CH 3 or H;

[0082] The R 3 and R 4 It is also possible to cyclosynthesize cyclopentyl, cyclohexyl, 4-tetrahydropyranyl or cycloheptyl;

[0083] Ar 1 selected from phenyl, 4-chlorophenyl, 4-bromophenyl, 4-...

Embodiment 1

[0127] Dissolve 1-phenyl-5-methyl-4-hexen-1-one (1.0 equiv) in methanol, add p-toluenesulfonyl hydrazide (1.1 equiv) at room temperature, and react for 24 hours to obtain N-4-methyl phenylsulfonyl-1-phenyl-5-methyl-4-hexene-1-hydrazone. Add the obtained unsaturated hydrazone (1.0 equiv), potassium pivalate (1.0 equiv), tris(2,2'-bipyridyl) ruthenium bis(hexafluorophosphate) salt (0.03 equiv) into a sealed tube, and argon After three replacements, dichloroethane was added and reacted for 12 hours under 22W blue light to obtain 3-phenyl-6-[1,1-dimethyl-1-(4-methylphenyl)]methylene- 1,4,5,6-tetrahydropyridazine (I-1), yield 85%.

[0128] 1 H NMR (400MHz, CDCl 3 )δ7.64(d, J=7.3Hz, 2H), 7.35(dd, J=4.9, 2.9Hz, 3H), 7.32–7.26(m, 2H), 7.21(d, J=7.9Hz, 2H), 5.39(s,1H),3.20(d,J=11.0Hz,1H),2.71(dd,J=8.6,4.3Hz,2H),2.39(s,3H),2.18–2.05(m,1H),1.96 –1.79(m,1H),1.44(d,J=12.6Hz,6H); 13 C NMR (150MHz, CDCl 3 )δ143.9, 143.0, 138.5, 135.9, 129.2, 128.2, 128.1, 127.6, 126.1, 124.2, 60.5, 39...

Embodiment 2

[0130]Dissolve 1-(4-chlorophenyl)-5-methyl-4-hexen-1-one (1.0 equiv) in methanol, add p-toluenesulfonyl hydrazide (1.1 equiv) at room temperature, and react for 24 hours to obtain N-4-Methylbenzenesulfonyl-1-(4-chlorophenyl)-5-methyl-4-hexene-1-hydrazone. Add the obtained unsaturated hydrazone (1.0 equiv), potassium pivalate (1.0 equiv), tris(2,2'-bipyridine) ruthenium bis(hexafluorophosphate) salt (0.03 equiv) into a sealed tube, and argon After three replacements, dichloroethane was added and reacted under 22W blue light for 12 hours to obtain 3-(4-chlorophenyl)-6-[1,1-dimethyl-1-(4-methylphenyl) ] Methylene-1,4,5,6-tetrahydropyridazine (I-2), yield 71%.

[0131] 1H NMR (400MHz, CDCl 3 )δ7.57–7.44(m,2H),7.26(ddd,J=9.2,6.6,5.0Hz,4H),7.15(d,J=8.0Hz,2H),3.14(dd,J=11.2,2.1Hz ,1H),2.66–2.56(m,2H),2.33(s,3H),2.11–2.00(m,1H),1.88–1.72(m,1H),1.38(s,3H),1.36(s,3H ); 13 C NMR (100MHz, CDCl 3 )δ143.8,141.5,137.0,136.0,133.3,129.3,128.3,126.1,125.4,60.4,39.2,26.0,24.0,21.7,20.8,20...

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Abstract

The invention provides a 3-aryl-6-aralkyl-1, 4, 5, 6-tetrahydropyridazine compound which has a structure as shown in a formula I in the specification. According to the invention, gamma, delta-unsaturated N-aryl sulfonyl substituted hydrazone is subjected to cyclization rearrangement reaction through a light and ruthenium complex catalysis method so that the 3-aryl-6-aralkyl-1, 4, 5, 6-tetrahydropyridazine compound is prepared. The 3-aryl-6-aralkyl-1, 4, 5, 6-tetrahydropyridazine compound prepared by the method has a specific compound structure. The preparation method has the advantages of high yield, short synthetic route, environmental protection, simple post-treatment and wide substrate applicability, and effectively overcomes the defects of large substrate limitation, troublesome post-treatment and the like in the existing synthetic route.

Description

technical field [0001] The invention relates to the technical field of nitrogen-containing heterocyclic compounds, in particular to a 3-aryl-6-aralkyl-1,4,5,6-tetrahydropyridazine compound, a preparation method and application thereof. Background technique [0002] Nitrogen-containing heterocyclic compounds are ubiquitous in natural products, and most alkaloids have significant physiological activities. 1,4,5,6-tetrahydropyridazine is an important azabenzene compound, which is an important structural unit of biologically active compounds such as medicines and pesticides, and 1,4,5,6-tetrahydropyridazine The structure also exists in many medicinal animals, plants and drug skeletons, such as 1,4,5,6-tetrahydropyridazino[4,5-c]pyridazin-5-one compounds for the prevention of mammalian inflammatory diseases , calcium sensitizer levosimendan all contain 1,4,5,6-tetrahydropyridazine core and so on. Thus, such compounds containing the 1,4,5,6-tetrahydropyridazine structure play an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/04C07D409/04C07D405/04C07D409/06C07D237/26
CPCC07D237/04C07D409/04C07D405/04C07D409/06C07D237/26
Inventor 刘峰涂佳林敖桂珍
Owner 江苏冠瑜生物科技有限公司