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3-thiocyano imidazo[1,5-a]quinoline compound synthesis method

A technology of thiocyanimidazole and synthesis method, applied in directions such as organic chemistry, can solve problems such as complex reaction conditions, and achieve the effects of wide substrate range, high yield and mild reaction conditions

Active Publication Date: 2020-03-03
ANHUI UNIV OF SCI & TECH
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

None of the above synthetic methods involves the thiocyanation of imidazo[1,5-a]quinoline compounds, and the reaction conditions are complex, requiring the use of catalysts or additives, thus limiting the ability of thiocyano-substituted imidazo[1 ,5-a] Quinoline Compound Preparation and Structure-Activity Relationship Study

Method used

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Embodiment 1-9

[0029] According to the raw material ratio and reaction conditions in the claims, add imidazo[1,5-a]quinoline compound (II), precipitated sulfur or sublimed sulfur (IV), TMS- CN(III) and DMSO were added in a ratio of 1mmol:(2-3)mmol:(2-3)mmol:(5-10)mL, mixed and stirred at room temperature, and reacted at 80-90°C for 3.5-4.5h.

[0030] After the reaction was completed, the reaction solution was cooled to room temperature, the reaction solution was transferred to a separatory funnel, 30 ml of water was added to the separatory funnel, extracted with ethyl acetate (3 × 10mL), after drying over anhydrous sodium sulfate, the Silica gel column chromatography separation (developing agent is the mixture of ethyl acetate and sherwood oil, both volume ratios are 1:(3-6) purification obtains the corresponding imidazo[1,5-a]quinone substituted by thiocyano group phylloline compounds.

[0031] Table 1 raw material addition amount

[0032]

[0033] Table 2 Reaction Conditions

[0034]...

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Abstract

The invention belongs to the field of organic synthesis, and discloses a 3-thiocyano imidazo[1,5-a]quinoline compound synthesis method, which comprises: carrying out selective thiocyanation on the site 3 of an imidazo[1,5-a]quinoline compound at a temperature of 80-90 DEG C in the absence of a catalyst by using elemental sulfur and TMS-CN as novel thiocyano sources, and carrying out separation andpurification after the reaction is finished to obtain the imidazo[1,5-a]quinoline compound substituted by the thiocyano group at the site 3. According to the invention, the method has characteristicsof simple operation, no need of any catalyst, cheap and easily available raw materials, wide substrate application range, high yield and the like, and has wide application prospects in the fields ofbiological medicines, pesticides and optical materials.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 3-thiocyanoimidazo[1,5-a]quinoline compounds. Background technique [0002] Heterocyclic structural units containing thiocyano groups are widely found in the skeletons of compounds such as medicines, pesticides, and materials, and have significant biological activities in antibacterial and antiviral aspects. Imidazo[1,5-a]quinolines are a class of nitrogen-containing heterocyclic compounds that are widely used in the fields of biomedicine, pesticides and optical materials. Therefore, the research on the synthesis of thiocyano-substituted imidazo[1,5-a]quinoline compounds is of great significance, and it also has a profound impact on the screening of nitrogen-containing heterocyclic skeleton drugs containing thiocyano. [0003] In 2015, the Shubhanjan Mitra group reported the use of visible light-driven photoredox pathways to synthesize thiocya...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 彭亚冯承涛丁光荣李祥晓
Owner ANHUI UNIV OF SCI & TECH
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