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Nitrate group transfer reagent as well as preparation method and application thereof

A technique of nitrate and radical transfer, applied in the field of nitrate-based transfer reagent compound and its synthesis, novel aryl acyclic trivalent iodine nitrate-based transfer reagent and preparation thereof, can solve the complicated post-processing process and the application of substrates narrow range, poor atom economy, etc., to avoid column chromatography, significant social and economic benefits, and easy operation.

Pending Publication Date: 2022-05-06
SHANGHAI NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The third category is the nitrate transfer reagent represented by cyclic trivalent iodine with o-iodobenzoic acid as the backbone, but it can only be used for the nitrate esterification reaction of 1,3-dicarbonyl compounds (Heterocycles, 1996, 42, 47; Angew.Chem., Int.Ed., 2020, 59, 17162; Org.Chem.Front., 2020, 7, 3509)
[0004] In summary, by comparing various nitrate ester synthesis methods, it is found that the existing nitrate ester synthesis generally has problems such as poor atom economy, poor selectivity, narrow substrate application range, low safety, cumbersome post-treatment process, and serious waste of materials.

Method used

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  • Nitrate group transfer reagent as well as preparation method and application thereof
  • Nitrate group transfer reagent as well as preparation method and application thereof
  • Nitrate group transfer reagent as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of phenyl acyclic trivalent iodine nitrate ester transfer reagent reacts according to the following reaction equation:

[0034]

[0035] The specific operation steps are:

[0036] 1) Dissolve compound 3a (iodobenzene, 12.2 g, 0.06 mol) in 200 ml of acetonitrile at room temperature, and then add sodium hypochlorite (10 wt%, 120 ml), water (200 ml) and analytically pure Concentrated hydrochloric acid (120 ml), stirred and reacted for 1 hour, filtered, washed with water, and dried to dichloroiodobenzene 2a (14.7 g, 89% yield);

[0037] 2) Dissolve compound 2a (dichloroiodobenzene, 13.8 g, 0.05 mol) in 300 ml of dichloromethane at room temperature in a nitrogen atmosphere, then add silver nitrate (25.5 g, 0.15 mol), stir overnight, and filter Silver chloride was removed, concentrated to obtain a yellow oil, dissolved in 50 milliliters of dichloromethane, then added an appropriate amount of water (0.5 liters per mole) and stirred for 30 minutes to obtain ...

Embodiment 2

[0041] The preparation of p-fluorophenyl acyclic trivalent iodine nitrate ester transfer reagent reacts according to the following reaction equation:

[0042]

[0043] The specific operation steps are:

[0044] 1) At room temperature, dissolve compound 3b (0.005 moles) in 20 milliliters of acetonitrile, and then add sodium hypochlorite (10 wt%, 10 milliliters), water (20 milliliters) and analytically pure concentrated hydrochloric acid (10 milliliters) in succession under stirring , stirred and reacted for 1 hour, filtered, washed with water, and dried to dichloroiodobenzene 2b (71% yield);

[0045] 2) Dissolve compound 2b (0.003 mol) in 20 ml of dichloromethane at room temperature in a nitrogen atmosphere, then add silver nitrate (0.09 mol), stir overnight, remove silver chloride by filtration, and concentrate to obtain a yellow oil. After being dissolved in 10 milliliters of dichloromethane, add a drop of water and stir for 10 minutes to obtain the nitrate group transfer...

Embodiment 3

[0049] The preparation of m-chlorophenyl acyclic trivalent iodine nitrate transfer reagent reacts according to the following reaction equation:

[0050]

[0051] The specific operation steps are:

[0052] 1) Dissolve compound 3c (0.005 mole) in 20 ml of acetonitrile at room temperature, and then add sodium hypochlorite (10 wt%, 10 ml), water (20 ml) and analytically pure concentrated hydrochloric acid (10 ml) in succession under stirring , stirred and reacted for 1 hour, filtered, washed with water, and dried to dichloroiodobenzene 2c (60% yield);

[0053] 2) Dissolve compound 2c (0.003 mol) in 20 ml of dichloromethane at room temperature in a nitrogen atmosphere, then add silver nitrate (0.09 mol), stir overnight, remove silver chloride by filtration, and concentrate to obtain a yellow oil. After being dissolved in 10 milliliters of dichloromethane, add a drop of water and stir for 10 minutes to obtain the nitrate group transfer reagent compound 1c (86% yield), a yellow s...

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Abstract

The invention relates to a nitrate group transfer reagent as well as a preparation method and application thereof, in particular to a novel organic acyclic trivalent iodine nitrate group transfer reagent and a preparation method thereof. The nitrate ester group transfer reagent has a general formula: the structure of the nitrate ester group transfer reagent is an acyclic trivalent iodine ether structure with an iodine-oxygen-iodine skeleton. Compared with the prior art, the reagent disclosed by the invention takes iodobenzene as a starting raw material, and a pure product can be obtained through two-step reaction and recrystallization, so that the reagent has the advantages of easily available raw materials, simplicity and convenience in operation, high synthesis efficiency, high product yield, high product purity and the like. The reagent is good in stability and high in reaction activity, and various nitric acid esterification reactions can be achieved without a catalyst.

Description

technical field [0001] The present invention relates to the field of organic synthesis chemistry, in particular to a nitrate group transfer reagent compound and a synthesis method thereof, in particular to a novel aryl acyclic trivalent iodine nitrate group transfer reagent, a preparation method thereof and the use of the reagent in an organic synthesis method use in the academic field. Background technique [0002] Nitrate compounds are not only widely used in petrochemical, material science, military fields, dyes, and sugar production; as the most common donor of nitric oxide (NO), they are used in the treatment of cardiovascular, immune, and nervous systems. It has a wide range of applications in diseases and is also a potential anti-tumor drug. Commonly used clinical drugs include nitroglycerin (NTG), isosorbide mononitrate (ISMN), isosorbide dinitrate (ISDN), nipradilol, Nicorandil, etc. In addition, studies have found that introducing nitrate functional groups into d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/02
CPCC07C201/02C07C203/02C07C17/00C07C67/307C07C253/30C07C255/50C07C201/12C07C205/12C07C231/12C07B43/00C07C2602/08C07C2602/10C07C25/02C07C25/13C07C69/78C07C203/08C07C235/40
Inventor 邓清海成轩殷权江岭峰
Owner SHANGHAI NORMAL UNIVERSITY
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