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Method for compounding nitrogenous polynary heterocyclic compound

A technology for heterocyclic compounds and compounds, which is applied in the field of synthesizing nitrogen-containing polyheterocyclic compounds, can solve problems such as no method has been found, and achieve the effects of good functional group compatibility, simple and efficient preparation method, and simple and easy-to-obtain raw materials

Active Publication Date: 2018-01-19
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But how to obtain the nitrogen-containing polyheterocyclic core structure [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-one, [1,2,3] Triazolo[4,5-c]quinolin-4-one and pyrrolo[3,2-c]quinolin-4-one derivatives, no suitable method found in previous work

Method used

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  • Method for compounding nitrogenous polynary heterocyclic compound
  • Method for compounding nitrogenous polynary heterocyclic compound
  • Method for compounding nitrogenous polynary heterocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of compound 6a

[0038]

[0039] Compounds 1a (1.0mmol) and 2a (1.0mmol) were stirred in EtOH for 0.5h, then 3a (1.0mmol) was added to continue stirring at room temperature for 0.5h, then 4a (1.0mmol) was added, and the four components were stirred at room temperature for 24h. Add NaN after spin off the solvent 3 (1.2mmol) and CuI (5mol%), DMSO was added under the protection of argon, and the reaction was complete at 90°C (18h). Water was added and extracted with ethyl acetate, the organic phases were combined, washed with water, dried, and concentrated to obtain the crude compound 5a.

[0040] Dissolve compound 5a in trifluoroacetic acid at 80°C and stir until the reaction is complete (28h), add saturated NaHCO 3 The pH value was adjusted to 8-9, and ethyl acetate was added to separate and extract the aqueous phase, and then the organic phases were combined, washed with water, dried, concentrated and filtered to obtain a yellow solid, n...

Embodiment 2

[0041] Embodiment 2: the synthesis of compound 6b

[0042]

[0043] Dissolve compound 1b (1.0mmol) and 2b (1.0mmol) in MeOH and stir for 0.5h, then add 3a (1.0mmol) and continue stirring for 0.5h, then add 4b (1.0mmol), and stir for 24h. Spin off the solvent, add NaN 3 (1.2mmol) and CuBr (10mol%), DMF was added under argon protection, and the reaction was complete at 100°C (4h). Water was added and extracted with ethyl acetate. The organic phases were combined, washed with water, dried, and concentrated to obtain the crude compound 5b.

[0044] Dissolve compound 5b in toluene, add hydrochloric acid (2mmol) and stir at 90°C until the reaction is complete (6-8h), add NaOH to adjust the pH value to 8-9, add ethyl acetate to separate and extract the aqueous phase, combine the organic phases, wash with water and Dry, concentrate and filter to obtain a yellow solid, namely compound 6b, with a yield of 50%. The characterization data of compound 6b are: 1 H NMR (400MHz, DMSO) ...

Embodiment 3

[0045] Embodiment 3: the synthesis of compound 6c

[0046]

[0047] Compounds 1c (1mmol) and 2c (1mmol) were dissolved in i-PrOH and stirred for 0.5h, then 3b (1mmol) was added and stirred for 0.5h, then 4a (1mmol) was added, and the four components were stirred for 24h. Spin off the solvent, add NaN 3 (1.2mmol) and CuCl (20mol%), DMSO was added under the protection of argon, and the reaction was complete at 100°C (6h). Water was added, and the aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed with water, dried, and concentrated to obtain a crude compound 5c.

[0048] Dissolve compound 5c in DMSO, add sulfuric acid (2mmol) and stir at 80°C until the reaction is complete (6-8h), add NaOH to adjust the pH value to 8-9, add ethyl acetate to extract the aqueous phase, combine the organic phase, and wash the organic phase with water. phase and dried, concentrated and filtered to obtain a yellow solid, namely compound 6c, with a yield ...

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Abstract

The invention belongs to the field of chemical synthesis and discloses a method for compounding a nitrogenous polynary heterocyclic compound. The method comprises the following steps: (1) performing Ugi four-component reaction on aldehyde RCHO, iso-nitrile compound R'NC, o-halide arylamine and substituted propiolic acid R2-C is equivalent to C-CO2H under the solvent existence condition and removing the solvent after ending the reaction, thereby acquiring a product of the step (1); (2) performing consecutive reaction on the product acquired in the step (1) and 1,3-dipole reaction reagent underthe catalytic effect of cupric salt under the solvent existence condition and the inert atmosphere and then purifying the acquired reaction solution, thereby acquiring the product acquired in the step(2); (3) performing acid promotion reaction on the product acquired in the step (2) and the acid under a heating condition with or without solvent and purifying the acquired reaction solution after ending the reaction, thereby acquiring a target product. The method has wide substrate applicability; the preparation method is simple and efficient; the nitrogenous polynary heterocyclic compound hashigh functional group compatibility and wide popularizing prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for synthesizing nitrogen-containing polyheterocyclic compounds. Background technique [0002] Nitrogen-containing polyheterocyclic structures such as [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-one, [1,2,3]triazolo[4, 5-c]quinolin-4-one, pyrrolo[3,2-c]quinolin-4-one, etc., are key structures in many compounds with important biological activities [(a) Biagi, G.; Giorgi , I.; Livi, O.; Scartoni, V.; Betti, L.; Giannaccini, G.; .; Nakasato, Y.; Manabe, H.; Ohmori, K.; Kitamura, S.; ; Ife, R.J.; Keeling, D.J.; Laing, S.M.; Parsons, M.E.; Price, C.A.; There are few methods reported in the literature for the synthesis of these structures, and the synthesis of these structures by the reported traditional synthesis methods has disadvantages such as complicated steps, low yields, and narrow scope of application. [0003] Recently, it has been reported in the literature that the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D471/04
Inventor 蔡倩
Owner JINAN UNIVERSITY
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