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Method for the selective synthesis of pyrazolo[1,2-a]pyrazolones or 2-acylindole compounds

A technology for acylindole and compounds, which is applied in the field of organic synthesis, can solve the problems of unavailable raw materials, single product structure, and low atom economy, and achieve the effects of cheap raw materials, simple synthesis process, and high atom economy

Active Publication Date: 2021-04-13
HENAN NORMAL UNIV
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Problems solved by technology

[0004] At present, the synthesis methods of pyrazolo[1,2-a]pyrazolone and 2-acylindole compounds have been reported in the existing literature, but these methods still have the disadvantages that the raw materials are not easy to obtain, the synthesis route is long, and the product structure is single and low atom economy

Method used

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  • Method for the selective synthesis of pyrazolo[1,2-a]pyrazolones or 2-acylindole compounds
  • Method for the selective synthesis of pyrazolo[1,2-a]pyrazolones or 2-acylindole compounds
  • Method for the selective synthesis of pyrazolo[1,2-a]pyrazolones or 2-acylindole compounds

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Experimental program
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Effect test

Embodiment 1

[0020]

[0021] Add 1a (57 mg, 0.3 mmol), 2a (52 mg, 0.3 mmol), solvent (2 mL), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer ( [RhCp*Cl 2 ] 2 , 4.7mg, 0.0075mmol) and additives (0.06mmol), cover the stopper and seal it, place it in an oil bath and stir the reaction at a certain temperature. After the reaction, cool to room temperature, filter with suction, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=10 / 1 to petroleum ether / ethyl acetate=1 / 1) to obtain white solid product 3a or 4a.

[0022] By changing the solvent, additive, catalyst, temperature, time and substrate equivalent ratio of the reaction, the specific results of the reaction are shown in Table 1.

[0023] Synthesis of 3a and 4a under different reaction conditions in table 1 a

[0024]

[0025]

Embodiment 2

[0027] Add 1a (57mg, 0.3mmol), 2a (52mg, 0.3mmol), dichloromethane (2mL), dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer Body ([RhCp*Cl 2 ] 2 , 4.7mg, 0.0075mmol) and sodium acetate (4.9mg, 0.06mmol), capped and sealed, placed in an oil bath at 60°C and stirred for 8 hours. After the reaction was completed, it was cooled to room temperature, suction filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain white solid product 3a (94.6 mg, 87%). The characterization data of this compound are: 1 H NMR (600MHz, CDCl 3 )δ0.80(t, J=7.2Hz, 3H), 1.22(s, 3H), 1.43-1.49(m, 5H), 2.22-2.27(m, 1H), 2.37-2.43(m, 1H), 3.36 (d, J=18.0Hz, 1H), 3.47(d, J=7.8Hz, 1H), 3.79(d, J=7.8Hz, 1H), 4.30(d, J=18.0Hz, 1H), 6.75(d ,J=7.8Hz,1H),6.99(t,J=7.8Hz,1H),7.18(d,J=7.2Hz,1H),7.23(t,J=7.8Hz,2H),7.31(t,J =7.8Hz, 2H), 7.47(d, J=8.4Hz, 2H). 13 C{ 1 H}NMR (150MHz, CDCl 3 )δ13.6,16.9,22.3,23.8,45.1,45.4,47.8,64.5,68.4,110.1,122.32,122.33, 125.5...

Embodiment 3

[0029] According to the method and steps of Example 2, various pyrazolo[1,2-a]pyrazolone compounds 3 can be synthesized by changing the reactants 1 and 2, and the specific results are shown in Table 2.

[0030] Synthesis of various pyrazolo[1,2-a]pyrazolone compounds 3 in table 2 a,b

[0031]

[0032]

[0033] Representative product characterization data are as follows:

[0034] 7-Isopropyl-2,2-dimethyl-9-(2-oxopentyl)-9-phenyl-2,3-dihydropyrazolo[1,2-a]in dazol-1(9H)-one(3c)

[0035] White solid (94.7mg, 78%). 1 H NMR (400MHz, CDCl 3)δ0.79(t, J=7.6Hz, 3H), 1.22(s, 9H), 1.42-1.50(m, 5H), 2.21-2.29(m, 1H), 2.35-2.42(m, 1H), 2.84 -2.91(m, 1H), 3.39(d, J=17.6Hz, 1H), 3.43(d, J=8.0Hz, 1H), 3.76(d, J=8.0Hz, 1H), 4.29 (d, J= 18.0Hz, 1H), 6.68(d, J=8.0Hz, 1H), 7.02(s, 1H), 7.10(d, J=8.4Hz, 1H), 7.23(t, J=7.2Hz, 1H), 7.32 (t,J=7.6Hz,2H),7.47(d,J=8.0Hz,2H). 13 C{ 1 H) NMR (100MHz, CDCl 3 )δ 13.6, 16.9, 22.3, 23.7, 24.2, 24.4, 33.8, 45.2, 45.4, 47.7, 64.7, 68.5, 109.9, 120...

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Abstract

The invention discloses a method for selectively synthesizing pyrazolo[1,2-a]pyrazolone or 2-acylindole compounds, belonging to the technical field of organic chemistry. The method starts from 1-aryl pyrazolidinone compound 1 and alkynyl cyclobutanol compound 2, under the catalysis of dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer, By changing the reaction temperature, solvent and additives, pyrazolo[1,2‑a]pyrazolone 3 or 2‑acyl indole compound 4 was synthesized with high selectivity. The method has the advantages of simple and easy-to-obtain raw materials, simple operation, mild conditions, good selectivity and wide application range of substrates.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for selectively synthesizing pyrazolo[1,2-a]pyrazolone or 2-acylindole compounds. Background technique [0002] Pyrazolo[1,2-a]pyrazolones are an important class of nitrogen-containing fused heterocyclic compounds, which usually exhibit remarkable pharmaceutical properties, such as antibacterial, herbicidal, insecticidal, and Alzheimer's disease relief. [0003] 2-Acylindole compounds are not only ubiquitous in nature, but also often have good biological activity, physical and chemical properties, and have been widely used in medicine, pesticides, spices, food and feed additives, functional dyes and other fields. [0004] At present, the synthesis methods of pyrazolo[1,2-a]pyrazolone and 2-acylindole compounds have been reported in the existing literature, but these methods still have the disadvantages that the raw materials are not easy to obtain, the syntheti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C07D209/12C07D409/04C07D401/04C07D471/06B01J31/22
CPCB01J31/2295B01J2531/0263B01J2531/822C07D209/12C07D401/04C07D409/04C07D471/06C07D487/04
Inventor 张新迎沈檬洋徐园双范学森
Owner HENAN NORMAL UNIV
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