Alkynyl imine derivative

A hydrocarbon-based and aryl-based technology, applied in the field of alkynyl imine derivatives, can solve the problems of unavailable raw materials, poor regioselectivity, and low yield

Inactive Publication Date: 2013-07-24
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Raw materials are not easy to obtain, catalysts are needed, the reaction conditions are severe, the yield is low, the regioselectivity is poor, the functional group tolerance is poor, and the types of substituents are limited

Method used

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  • Alkynyl imine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 3

[0093] Embodiment 3——compound shown in preparation formula IVc (R 1 =R 2 = i Pr, R 3 =4-HCC-Ph, R 4 =R 5 =R 6 =R 7 =H):

[0094]

[0095] IVc

[0096] Under nitrogen protection, add 2 mmol o-trimethylsilylphenol triflate, 1 mmol N,N'-diisopropylcarbodiimide and 1 mmol 1,4-diethynylbenzene to a 25 mL reaction tube, add 3 mL THF dissolved. Then add 2.2mmol of anhydrous potassium fluoride and 2.2mmol of 18-crown-6, and react at room temperature (25°C) for 9 hours. The color of the reaction solution changed from colorless to yellow. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether: ethyl acetate: dichloromethane = 40:1:1 was used as an eluent to obtain N-{1-[2-(N-isopropyl- N-phenyl)phenyl]-3-(4-ethynylphenyl)-2-propynylalkenyl}-isopropylamine 316 mg (purity>98%, yellow oil), isolated yield 78%. The NMR data of this compound are as follows: 1 HNMR (400MHz, CD 2 Cl 2 , Me 4 Si): δ1.1...

Embodiment 4

[0097] Embodiment 4——compound shown in preparation formula IVd (R 1 =R 2 = i Pr, R 3 =4-NC-Ph,R 4 =R 5 =R 6 =R 7 =H):

[0098]

[0099] IVd

[0100] Under nitrogen protection, add 2mmol o-trimethylsilylphenol trifluoromethanesulfonate, 1mmol N,N'-diisopropylcarbodiimide and 1mmol p-cyanophenylacetylene to a 25mL reaction tube, add 3mL tetrahydrofuran to dissolve . Then add 2.2mmol of anhydrous potassium fluoride and 2.2mmol of 18-crown-6, and react at room temperature (25°C) for 9 hours. The color of the reaction solution changed from colorless to yellow. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether: ethyl acetate: dichloromethane = 40:1:1 was used as an eluent to obtain N-{1-[2-(N-isopropyl- N-phenyl)phenyl]-3-(4-cyanophenyl)-2-propynylalkenyl}-isopropylamine 320 mg (purity>98%, yellow oil), isolated yield 79%. The NMR data of this compound are as follows: 1 HNMR (400MHz, CD 2...

Embodiment 5

[0101] Embodiment 5——compound shown in preparation formula IVe (R 1 =R 2 = i Pr, R 3 =4-PhCO-Ph,R 4 =R 5 =R 6 =R 7 =H):

[0102]

[0103] IVe

[0104] Under nitrogen protection, add 2 mmol o-trimethylsilylphenol triflate, 1 mmol N,N'-diisopropylcarbodiimide, and 1 mmol 1-phenyl-2-propyne-1 to a 25 mL reaction tube - Ketone, add 3mL tetrahydrofuran to dissolve. Then add 2.2mmol of anhydrous potassium fluoride and 2.2mmol of 18-crown-6, and react at room temperature (25°C) for 9 hours. The color of the reaction solution changed from colorless to dark red. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether: ethyl acetate: dichloromethane = 40:1.5:1.5 was used as an eluent to obtain N-{1-[2-(N-isopropyl- N-phenyl)phenyl]-3-benzoyl-2-propynylalkenyl}-isopropylamine 343mg (purity>98%, dark red oily), isolated yield 84%. The NMR data of this compound are as follows: 1 HNMR (400MHz, CD 2 Cl ...

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PUM

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Abstract

The invention provides an alkynyl imine derivative and a synthesis method thereof. According to the method, the 1-o-amino aryl substituted alkynyl imine derivative is prepared from carbodiimide, terminal alkyne, benzyne precursors and activated fluorine ions, the yield is high, and the synthesis method is scientific and reasonable, so that the universal method for synthesizing the alkynyl imine derivative with multiple substituent groups is provided. The method has the advantages of easily-obtained raw materials, wide application range and high separation yield; and experimental equipment and operation are simple and feasible, and further development and application are facilitated.

Description

technical field [0001] The invention relates to an alkynyl imine derivative, in particular to an alkynyl imine derivative substituted by an aryl group of an o-amino group and a synthesis method thereof. Background technique [0002] Alkynyl imine derivatives with various substituents have alkynyl imine fragments in their molecules, which are important synthons in organic synthesis and can be used to synthesize a series of nitrogen-containing heterocyclic compounds. They are also useful in pharmaceutical synthesis and material research. important application. [0003] As described below, the use of 1-alkynimine compounds in synthesis has been reported. [0004] "A Multicomponent Reaction of Arynes, Isocyanides, and Terminal Alkynes: Highly Chemo-and Regioselective Synthesis of Polysubstituted Pyridines and Isoquinolines. Angew. Chem. Int. Ed. 2009, 48, 3458" records that alkynyl imines can be synthesized by reacting with alkynes Pyridine derivatives react with benzyne to sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/24C07C255/61C07D333/22C07C249/02C07C253/30C07D209/52
Inventor 张文雄周易席振峰
Owner PEKING UNIV
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