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Isoquinoline salt synthesis method
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A technology of isoquinolinium salts and compounds, applied in the field of synthesizing isoquinolinium salts
Inactive Publication Date: 2014-12-03
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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For example: Method 1, although the reaction conditions are mild, but requires expensive reactants and catalysts, and the expansion of the reaction substrate is severely limited; Method 2, although the reaction can occur at room temperature, but the reaction is an equivalent reaction, the reaction needs to be divided The first step requires a large amount of precious metal catalysts, and only one alkyne can be used as a reactant; the third method, although the method has been improved a lot, but the reaction requires an equivalent amount of expensive metal AgBF4 as an oxidant Requires high temperature of 120oC, atom economy is not high
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Embodiment 1
[0033] Embodiment 1, the preparation of trifluoromethanesulfonic acid isoquinoline salt derivative 3aa
[0036] 2-Phenylpyridine 1a (71 μL, 0.5 mmol), 1,2-tolanyl 2a (89.7 mg, 0.5 mmol), {[Cp*RhCl 2 ] 2} (3.1 mg, 1 mol %), AgOTf (5.1 mg, 0.02 mmol), Cu(OTf) 2 (180.8 mg, 0.5 mmol), added to 2.0 mL methanol, under argon (1atm), 120 o After 22 hours of reaction in C, stop the reaction, filter with diatomaceous earth, wash with dichloromethane, collect the organic phase, evaporate the solvent to dryness, and wash with methanol / ether / petroleumether (1:4:100) to obtain the pure isoquinoline salt derivative 3aa . The product was a white solid with a yield of 91%.
[0039] 2-Phenylpyridine 1a (71 μL, 0.5 mmol), 1,2-tolanyl 2a (89.7 mg, 0.5 mmol), {[Cp*RhCl 2 ] 2} (3.1 mg, 1 mol %), AgOTf (128.5 mg, 0.5 mmol), added to 2.0 mL methanol, under argon (1atm), 120 o After 22 hours of reaction in C, stop the reaction, filter with celite, wash with dichloromethane, collect the organic phase, evaporate the solvent to dryness, wash with methanol / ether / petroleum ether (1:4:100), and obtain the pure isoquinoline salt derivative 3aa . The product is a white solid with a yield of 96%. Data characterization is the same as in Example 1.
[0041] 2-Phenylpyridine 1a (71 μL, 0.5 mmol), 1,2-tolanyl 2a (89.7 mg, 0.5 mmol), {[Cp*RhCl 2 ] 2} 2 (3.1 mg, 1 mol %), AgOTf (5.1 mg, 0.02 mmol), HOTf (44 μL, 0.5 mmol), added to 2.0 mL methanol, under oxygen (1atm), 120 o After 22 hours of reaction in C, stop the reaction, filter with celite, wash with dichloromethane, collect the organic phase, evaporate the solvent to dryness, wash with methanol / ether / petroleum ether (1:4:100), and obtain the pure isoquinoline salt derivative 3aa . The product is a white solid with a yield of 99%. Data characterization is the same as in Example 1.
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Abstract
The invention discloses a substituted isoquinolinium salt preparation method which is as follows: using oxygen as an oxidant and various substituent group-substituted aromatic hydrocarbons, alkynes and acids as starting materials for catalysis with transition metals to obtain a compound containing an isoquinolinium salt structure. The reaction raw materials, oxidant and catalyst are cheap, the synthesis process is simple, the synthetic cost is greatly reduced; reaction condition is mild, the yield is high, industrialization is easy; the reaction raw materials and the catalyst are clean, nontoxic and low in pollution to environment. The compound and derivatives thereof as important fine chemicals can be widely used in medicines, pesticides, flavors and photoelectric and other industries.
Description
technical field [0001] The present invention relates to a kind of compound containing isoquinoline salt structure and the preparation method of substituted isoquinoline salt, specifically, the preparation method adopts aromatic hydrocarbons substituted by various substituents, alkynes and acids as starting materials, Through transition metalcatalysis, compounds containing isoquinoline salt structures are obtained, and various substituted isoquinoline compounds can be obtained by simple conversion of such compounds. Background technique [0002] As an important fine chemical, isoquinolinium salt is widely used in pesticide, medicine, spices and other industries. [0003] Isoquinolinenitrogen-containing heterocyclic ring is a common pharmacophore, which widely exists in various natural products and synthetic drugs with physiological activity, and is also a fragment that constitutes various functional materials. For example, Coralyne, which is an antiscorbutic drug ( J. Het...
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