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Method for selectively synthesizing pyrazolo[1,2-a] pyrazolone or 2-acyl indole compound

An acyl indole and compound technology, applied in the field of organic synthesis, can solve the problems of single product structure, difficult to obtain raw materials, low atom economy and the like, and achieve the effects of simple synthesis process, cheap raw materials and high atom economy

Active Publication Date: 2020-07-31
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 selectively synthesizing pyrazolo[1,2-a] pyrazolone or 2-acyl indole compound
  • Method for selectively synthesizing pyrazolo[1,2-a] pyrazolone or 2-acyl indole compound
  • Method for selectively synthesizing pyrazolo[1,2-a] pyrazolone or 2-acyl indole compound

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Experimental program
Comparison scheme
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, filtered with suction, spin-dried, and separated through a silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the product 3a (94.6 mg, 87%) as a white solid. 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...

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 a pyrazolo[1,2-a] pyrazolone or 2-acyl indole compound, and belongs to the technical field of organic chemistry. Starting from a 1-aryl pyrazolidone compound 1 and an alkynyl cyclobutanol compound 2, the pyrazolo[1,2-a] pyrazolone compound 3 or 2-acyl indole compound 4 is synthesized with high selectivity by changing the reaction temperature, solvent and additive types under the catalysis of a dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer. The method has the advantages of simple and easily available raw materials, simplicity and convenience in operation, mild conditions, good selectivity, wide substrate application range and the like.

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 synthesi...

Claims

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Application Information

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Patent Type & Authority Applications(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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