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A kind of iminoxazine derivative and preparation method thereof

A technology of iminoxazine and derivatives, applied in the field of organic chemical synthesis, can solve the problems of harsh reaction conditions, many reaction steps, expensive principles, etc., and achieve the effects of high purity, high yield, and high atom economy

Active Publication Date: 2022-04-19
MARINE MEDICAL RES INST OF GUANGDONG ZHANJIANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Different methods for preparing 1,3-oxazine have been reported in the existing literature, but the principle is expensive, difficult to obtain, many reaction steps, harsh reaction conditions, low yield, and there is no very effective and widely adaptable method

Method used

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  • A kind of iminoxazine derivative and preparation method thereof
  • A kind of iminoxazine derivative and preparation method thereof
  • A kind of iminoxazine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add the compounds of the above formulas (II), (III) and (IV) and cuprous iodide (CuI) into acetonitrile, then raise the temperature to 80° C., and stir and seal the reaction at this temperature for 6 hours.

[0032] Wherein, the molar ratio of formula (II) compound and cuprous iodide (CuI) is 1:0.1; The molar ratio of formula (II) compound and (III), (IV) compound is 1:2:2; The ratio of the compound of formula (II) in moles (mmol) to acetonitrile in milliliters (ml) is 1:3.

[0033] After the reaction, the reaction system was naturally cooled to room temperature, and the solvent was concentrated by rotary evaporation to obtain a crude product. The crude product was subjected to 300-400 mesh silica gel column chromatography, using a mixture of ethyl acetate and petroleum ether as an eluent, wherein acetic acid Ethyl ester and sherwood oil volume ratio 1:4, thus obtain the target product formula (I) compound (C 19 h 20 N 2 o 3 S) with a yield of 82% and a purity of 95...

Embodiment 2

[0038] Add the compounds of the above formulas (II), (III) and (IV) and cuprous iodide (CuI) into acetonitrile, then raise the temperature to 60° C., and stir and seal the reaction at this temperature for 8 hours.

[0039] Wherein, the molar ratio of formula (II) compound and cuprous iodide (CuI) is 1:0.2; The molar ratio of formula (II) compound and (III), (IV) compound is 1:1.2:1.2; The ratio of the compound of formula (II) in moles (mmol) to acetonitrile in milliliters (ml) is 1:5.

[0040] After the reaction was complete, the reaction system was naturally cooled to room temperature, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was subjected to 200-300 mesh silica gel column chromatography, using a mixture of ethyl acetate and petroleum ether as an eluent, wherein The volume ratio of ethyl acetate and sherwood oil is 1:4, thereby obtains the target product formula (I) compound (C 20 h 22 N 2 o 3 S) with a yield of...

Embodiment 3

[0045] Add the compounds of formulas (II), (III) and (IV) and copper iodide (CuI) to acetonitrile, then raise the temperature to 40° C., and stir and seal the reaction at this temperature for 12 hours.

[0046] Wherein, the molar ratio of formula (II) compound and cuprous iodide (CuI) is 1:0.05; The molar ratio of formula (II) compound and (III), (IV) compound is 1:2.5:2.5; The ratio of the compound of formula (II) in moles (mmol) to acetonitrile in milliliters (ml) is 1:2.

[0047] After the reaction was complete, the reaction system was naturally cooled to room temperature, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was subjected to 200-300 mesh silica gel column chromatography, using a mixture of ethyl acetate and petroleum ether as an eluent, wherein The volume ratio of ethyl acetate and sherwood oil 1:6, thus obtain the target product formula (I) compound (C 19 h 19 ClN 2 o 3 S) with a yield of 75% and a purit...

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Abstract

The invention relates to a derivative of iminoxazine and a preparation method thereof, comprising the following steps: reacting a ketoxime compound with a ketynone compound and a sulfonyl azide under copper catalysis to obtain the iminoxazine oxazine derivatives. The invention has the advantages of high product yield, high purity, high atom economy, etc., has good scientific research value and application prospect, and provides a new route for the preparation of iminoxazine derivatives, which can be used in pharmaceutical intermediates, It plays an important role in the fields of pesticide intermediates and other fields, reduces production costs, and has good application value and potential in industry and scientific research.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a 2,2,4-trisubstituted-6-sulfonimide-1,3-dihydrooxazine derivative and a preparation method thereof. Background technique [0002] Oxazine is an important structural unit in natural products and drug molecules, and its derivatives have a variety of biological and pharmacological activities. , antidepressant activity. Its derivative resin can be well compounded with epoxy resin and phenolic resin, so as to obtain a composite material with better performance, which has the functions of antibiotics, catalyst molecules, fluorescent dyes, and dopamine receptors. Oxazine derivatives also play an important role in medicine and biology. In addition to their own functions, the existence of their skeletons makes natural products have significant biological activity. Different methods for preparing 1,3-oxazine have been reported in the existing literature, but the princ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/06
CPCC07D265/06
Inventor 杨渭光赵宇周子彤李立罗辉
Owner MARINE MEDICAL RES INST OF GUANGDONG ZHANJIANG
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