- Pyrazoloisoquinoline compound and synthesis method thereof
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The invention discloses a pyrazoleoisoquinoline compound and a synthesis method thereof. The pyrazoleoisoquinoline compound is represented by a formula I, wherein the R1 represents hydrogen, halogen atoms and alkyl or alkoxy or amino, and the R2 represents hydrogen, halogen atoms and alkyl or alkoxy or amino. The target product is synthesized through four-step reaction, the synthesis method is simple and rapid, the target compound is higher in yield, and a necessary foundation is provided for further research on the compound represented by the formula I or related compounds. In addition, the intermediate provided in the synthesis method is simple in structure and easy to obtain and provides convenience for the preparation of the target compound.
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- Aryne [3 + 2] cycloaddition with N-sulfonylpyridinium imides and in situ generated N-sulfonylisoquinolinium imides: A potential route to pyrido[1,2-b]indazoles and indazolo[3,2-a]isoquinolines
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The aryne [3 + 2] cycloaddition process with pyridinium imides breaks the aromaticity of the pyridine ring. By equipping the imide nitrogen with a sulfonyl group, the intermediate readily eliminates a sulfinate anion to restore the aromaticity, leading to the formation of pyrido[1,2-b]indazoles. The scope and limitation of this reaction are discussed. As an extension of this chemistry, N-tosylisoquinolinium imides, generated in situ from N′-(2-alkynylbenzylidene)-tosylhydrazides via an AgOTf-catalyzed 6-endo-dig electrophilic cyclization, readily undergo aryne [3 + 2] cycloaddition to afford indazolo[3,2-a]-isoquinolines in the same pot, offering a highly efficient route to these potential anticancer agents.
- Zhao, Jingjing,Li, Pan,Wu, Chunrui,Chen, Hongli,Ai, Wenying,Sun, Renhong,Ren, Hailong,Larock, Richard C.,Shi, Feng
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supporting information; experimental part
p. 1922 - 1930
(2012/04/23)
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- Generation of diverse 1-(isoquinolin-1-yl)guanidines via a sequential multi-component/cross-coupling reaction
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A multi-component reaction of 2-alkynylbenzaldehyde, 4- methylbenzenesulfonohydrazide, carbodiimide, and bromine is reported, which generates 1-(4-bromoisoquinolin-1-yl)guanidines in good yields under mild conditions. The products could be further elaborated via a palladium-catalyzed Suzuki-Miyaura coupling reaction, leading to the diverse 1-(isoquinolin-1-yl) guanidines.
- Ye, Chao,Chen, Zhiyuan,Wang, Huanhuan,Wu, Jie
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supporting information; experimental part
p. 5197 - 5202
(2012/08/07)
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- Synthesis of H-pyrazolo[5,1-a]isoquinolines via copper(II)-catalyzed oxidation of an aliphatic C-H bond of tertiary amine in air
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A multicomponent reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and tertiary amine is discovered, which generates the unexpected H-pyrazolo[5,1-a]isoquinolines in good yields under mild conditions. In the reaction process, silver(I)-catalyzed intramolecular cyclization and copper(II)-catalyzed oxidation of an aliphatic C-H bond of tertiary amine in air are involved.
- Li, Shaoyu,Wu, Jie
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supporting information; experimental part
p. 712 - 715
(2011/04/23)
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- Efficient generation of biologically active H-pyrazolo[5,1- a]isoquinolines via multicomponent reaction
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A highly efficient multicomponent reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, alcohol, and α,β-unsaturated aldehyde or ketone is disclosed, which generates the diverse H-pyrazolo[5,1-a]isoquinolines in good yields. This reaction proceeds with good functional group tolerance under mild conditions with high efficiency and excellent selectivity. Preliminary biological assays show that some of these compounds display promising activities as CDC25B inhibitor, TC-PTP inhibitor, and PTP1B inhibitor.
- Chen, Zhiyuan,Wu, Jie
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supporting information; experimental part
p. 4856 - 4859
(2011/02/22)
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