Amide compound as well as preparation method and application thereof

A kind of amide compound and compound technology, applied in the field of amide compound and its preparation, can solve the problems of complex reaction, easy dissociation, difficult coordination and the like

Active Publication Date: 2018-10-12
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, on the one hand, the reaction conditions of the above-mentioned literature are relatively harsh (the substrate reaction scale is 0.1 mmol, 120 ° C, 24 h), the substrate needs to be pre-installed with additional directing groups and it is difficult to transform or eliminate, and the reaction requires additional preparation difficulties. And the alkynylation reagent (Waser reagent) of expensive hypervalent iodine, therefore, this catalytic system obviously does not have practicability and economic value, has limited the further application of this method; On the other hand, with respect to nitrogen atom, oxygen The planarity of the atoms is relatively poor, and the complexation of the oxygen atom to the metal in the amide compound is weak, which makes it difficult for the subsequent functional groups to achieve high conversion even if the compo

Method used

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  • Amide compound as well as preparation method and application thereof
  • Amide compound as well as preparation method and application thereof
  • Amide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] The preparation of embodiment one 2-((triisopropylsilyl) acetylene) benzamide (3a)

[0108]

[0109] Under nitrogen atmosphere, arylsulfonamide compound 1a (12.1 mg, 0.10 mmol), alkynyl bromide or alkyne 2 (20 μL, 0.10 mmol), dichloro(pentamethylcyclopentadiene base) iridium dimer (2.3mg, 0.0025mmol) or dichloro(p-methylcumene) ruthenium dimer (1.5mg, 0.0025mmol), bis(trifluoromethanesulfonyl)imide silver ( 4.2mg, 0.015mmol) or silver hexafluoroantimonate (5.2mg, 0.015mmol), cesium acetate (30mg, 0.36mmol), (when the reaction uses an alkyne bromide, no additional oxidant is needed; when the reaction uses a terminal alkyne directly, You need 2 equivalents of silver acetate), 1,2-dichloroethane (DCE, 1mL), and react at 120°C for 12 hours. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain a crude product. The crude product was separated by chromatography on a prepared silica gel plate, ...

Embodiment 2

[0112] Preparation of Example Two 4-acetyl-2-((triisopropylsilyl)acetylene)benzamide (3b)

[0113]

[0114] Under nitrogen atmosphere, arylamide compound 1b (16.4 mg, 0.10 mmol), alkynyl bromide or alkyne 2 (30 μL, 0.15 mmol), dichloro(pentamethylcyclopentadienyl ) iridium dimer (2.3mg, 0.0025mmol) or dichloro(p-methylcumene) ruthenium dimer (1.5mg, 0.0025mmol), bis(trifluoromethanesulfonyl)imide silver (4.2 mg, 0.015mmol) or silver hexafluoroantimonate (5.2mg, 0.015mmol), cesium acetate (30mg, 0.36mmol), (when the reaction uses an alkyne bromide, no additional oxidant is needed; when the reaction uses a terminal alkyne directly, then Need 2 equivalents of silver acetate), 1,2-dichloroethane (DCE, 1mL), react at 120°C for 12 hours. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain a crude product. The crude product was chromatographically separated on a prepared silica gel plate, and the se...

Embodiment 3

[0118] Example 3 3-((triisopropylsilyl)acetylene)isonicotinamide (3c)

[0119]

[0120] Under nitrogen atmosphere, add arylamide compound 1c (12.2 mg, 0.10 mmol), alkyne 2 (40 μL, 0.40 mmol), dichloro(pentamethylcyclopentadienyl) iridium di polymer (2.3mg, 0.0025mmol) or dichloro(p-methylcymene) ruthenium dimer (1.5mg, 0.0025mmol), silver bis(trifluoromethanesulfonyl)imide (4.2mg, 0.015mmol ) or silver hexafluoroantimonate (5.2mg, 0.015mmol), cesium acetate (30mg, 0.36mmol), (when the reaction uses alkyne bromide, no additional oxidant is needed; when the reaction directly uses terminal alkynes, 2 equivalents of Silver acetate), 1,2-dichloroethane (DCE, 1mL), react at 120°C for 16 hours. After the reaction was completed, cool to room temperature, filter through diatomaceous earth, and concentrate the crude product obtained by chromatography on a prepared silica gel plate. The selected developer was petroleum ether and ethyl acetate with a volume ratio of 3:1. The product ...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to an amide compound as well as a preparation method and application thereof. The preparation method for the amide compound comprises the following step of under the existence of an inert solvent and the function of a catalyst, enabling a compound in a formula (II) and a compound in a formula (III) to react, so as toobtain a compound in a formula (I). The preparation method has the advantages that the primer is simple and is easy to obtain, the additional directing group-assisted direct alkynylation reaction of hydrocarbon bonds of common primary and secondary amides is avoided, the number of steps is fewer, the operation is simple and convenient, the efficiency is high, the selectivity is good, and the economic and environment-friendly effects are realized; the application range of the primer is very broad, and the atom economy is good. The amide compound prepared by the preparation method is a fully novel amide compound, has a broad application range, and can solve the problems of complicated synthesis reaction and narrower primer application range in the existing amide compound.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an amide compound and its preparation method and application. Background technique [0002] Alkynes are a very general class of functional groups, ubiquitous from common simple synthetic building blocks, to synthetic intermediates, biomolecules, and natural products. The ubiquity of carbon-carbon triple bonds has also stimulated long-standing research interest in this type of functional group, including laboratory and industrial synthesis. Since the emergence of the Sonogashira reaction using palladium and copper synergistic catalysis in the 1970s, the synthesis of alkynes has made great progress, and has developed in the direction of atom and step economy. As an important class of alkynes, o-amidoarylacetylenes can not only be used as key intermediates to rapidly synthesize complex molecules through the Diels-Alder reaction, but also the potential biological activity ...

Claims

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Application Information

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IPC IPC(8): C07F7/10
CPCC07F7/0812C07F7/083
Inventor 李先纬吴国才霍延平
Owner GUANGDONG UNIV OF TECH
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