Tetrahydropyrrolooxazinone and piperidino-oxazinone compounds and preparation method thereof

A technology of tetrahydropyrrole and oxazinone, which is applied in the field of tetrahydropyrroloxazinone and piperidoxazinone compounds and their preparation, can solve problems such as adverse effects on human health and the environment, urgent problems, etc., and achieve a simple route , simple operation, high yield effect

Pending Publication Date: 2020-12-29
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The report discloses that my country is a populous country, and grain production is related to the national economy and the people's livelihood; in the process of producing and storing grain, there will be considerable losses due to diseases and insect pests every year, a...

Method used

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  • Tetrahydropyrrolooxazinone and piperidino-oxazinone compounds and preparation method thereof
  • Tetrahydropyrrolooxazinone and piperidino-oxazinone compounds and preparation method thereof
  • Tetrahydropyrrolooxazinone and piperidino-oxazinone compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of compound 3a

[0033] (4a S ,5 S )-5-( tert -Butyldimethylsilyloxy)-3- p -tolyl-5,6,7,8-tetrahydropyrido[1,2-c][1,3]oxazin-1(4a H )-one (3a)

[0034] -50 o Under the protection of C nitrogen, slowly drop boron trifluoride ether into compound 2b and dichloromethane solution of p-methylphenylacetylene to react for 0.5-5 hours, then naturally rise to room temperature, add aqueous solution of sodium bicarbonate, and react at room temperature for 5-10 minutes , extracted, dried over anhydrous sodium sulfate, filtered with suction, concentrated, and purified on a silica gel column to obtain white solid 3a (78 mg, 72%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.53-7.46 (m, 2H), 7.20-7.12 (m, 2H), 5.31-5.22 (m, 1H), 4.46 (d, J =13.2 Hz, 1H), 4.01-3.95 (m, 1H), 3.76-3.69 (m, 1H), 2.82-2.71 (m, 1H), 2.34(s, 3H), 2.16-2.04 (m, 1H), 1.94-1.86 (m, 1H), 1.69-1.60 (m, 1H), 1.47-1.40(m, 1H), 0.79 (s, 9H), 0.01 (s, 3H), -0.11 (s, 3H) ppm.

[0035] Synthesis of compound 3b

...

Embodiment 2

[0102] Synthesis of compound 3a

[0103] (4a S ,5 S )-5-( tert -Butyldimethylsilyloxy)-3- p -tolyl-5,6,7,8-tetrahydropyrido[1,2-c][1,3]oxazin-1(4a H )-one (3a)

[0104] -50 o Under nitrogen protection, slowly add copper trifluoromethanesulfonate to compound 2b and react with dichloromethane solution of p-methylphenylacetylene for 0.5-5 hours, then naturally rise to room temperature, add aqueous solution of sodium bicarbonate, and react at room temperature for 5-10 minutes , extracted, dried over anhydrous sodium sulfate, filtered with suction, concentrated, and purified on a silica gel column to obtain a white solid 3a (52 mg, 48%).

Embodiment 3

[0106] Synthesis of compound 3a

[0107] (4a S ,5 S )-5-( tert -Butyldimethylsilyloxy)-3- p -tolyl-5,6,7,8-tetrahydropyrido[1,2-c][1,3]oxazin-1(4a H )-one (3a)

[0108] -50 o Under the protection of C nitrogen, slowly add trifluoroacetic acid to compound 2b and react with the dichloromethane solution of p-methylphenylacetylene for 0.5-5 hours, then naturally rise to room temperature, add aqueous solution of sodium bicarbonate, react at room temperature for 5-10 minutes, and extract , dried over anhydrous sodium sulfate, filtered with suction, concentrated, and purified on a silica gel column to obtain a white solid 3a (11 mg, 10%).

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Abstract

The invention belongs to the technical field of chemical synthesis, and relates to a tetrahydropyrrolooxazinone and piperidino-oxazinone compounds and a preparation method thereof. The compound containing an oxazinone skeleton is prepared and has a wide range of biological activities such as weeding, insect killing, sterilization, inflammation diminishing, non-nucleoside reverse transcriptase inhibition, phosphodiesterase inhibition, antithrombotic activity, analgesia and the like, is also a core skeleton compound for preparing halofuginone and halofuginine with antimalarial and anticancer activities and the like, and is of great significance to research and development of novel pesticides. The preparation method disclosed by the invention has the characteristics of simple reaction conditions, high selectivity and capability of carrying out large-scale preparation.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, relates to a class of tetrahydropyrroloxazinone and piperidoxazinone compounds and a preparation method thereof, and is of great significance to the research and development of new pesticides. Background technique [0002] The report discloses that my country is a populous country, and grain production is related to the national economy and the people's livelihood; in the process of producing and storing grain, there will be considerable losses due to diseases and insect pests every year, and pesticides have become a rigid demand in grain production, but improper use of pesticides will affect human health. Therefore, it is urgent to develop "green" pesticides with low toxicity, high efficiency, good selectivity, novel structure and good environmental compatibility. [1] . [0003] In recent years, nitrogen-containing heterocyclic compounds with a wide range of biological activities have become a ...

Claims

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Application Information

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IPC IPC(8): C07F7/18C07D498/04
CPCC07F7/1804C07F7/1892C07D498/04
Inventor 魏邦国汪晨司长梅韩盼毛卓亚周祝
Owner FUDAN UNIV
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