A kind of preparation method of the alkynyl imine compound containing α-h

A technology of alkynyl imines and compounds, which is applied in the field of organic synthesis, can solve the problems of inability to synthesize alkynyl imine compounds, waste of thionyl chloride or oxalyl chloride, cumbersome steps, etc., and achieve strong substrate design and easy Good effect of operation and activity

Active Publication Date: 2018-03-27
JIAXING UNIV
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Problems solved by technology

[0005] This method cannot synthesize α-H-containing alkynyl imine compounds, and requires precious metal reagents such as palladium. The steps are cumbersome, the operation is troublesome, and a large amount of thionyl chloride or oxalyl chloride is wasted, which pollutes the environment and limits this type of synthetic method. Applications

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  • A kind of preparation method of the alkynyl imine compound containing α-h
  • A kind of preparation method of the alkynyl imine compound containing α-h
  • A kind of preparation method of the alkynyl imine compound containing α-h

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Embodiment 1～8

[0038] The molar ratio of raw materials is as follows: phosphoroimide compound (II): acyl chloride (III) containing α-H: alkynyl copper compound (IV)=1:1.2:1.8. Add phosphoroimide (II) into a 50ml Schlenk tube, vacuumize and change nitrogen three times, cool down to -78°C, add α-H-containing acid chloride (III) and 5ml of organic solvent dropwise, stir for 1 hour, then drop into Copper(IV) alkynes prepared in situ. After the dropwise addition was complete, the reaction was moved to room temperature for another 2-3 hours. After the spot plate detection reaction is completed, the reaction is quenched, the liquid is extracted and separated, the sample is mixed with silica gel, and purified by column chromatography (eluent is petroleum ether: ethyl acetate = 30:1) to obtain the corresponding alkynyl group containing α-H Imine compound (I), the yield of each product is shown in Table 1. The reaction process is shown in the following formula:

[0039]

[0040] The reaction yie...

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Abstract

The invention discloses a method for preparing an alkynyl enimic compound containing alpha-H through a one-pot reaction. The method comprises the steps that at the temperature of -78 DEG C, a phosphorus imine compound and acyl chloride containing alpha-H are reacted in an organic solvent to generate corresponding chloro imine which has a coupling reaction with alkynyl copper prepared on site, aftertreatment is carried out, and the alkynyl enimic compound containing alpha-H is obtained. The invention further discloses a compound prepared from the method. The preparation method of the alkynyl enimic compound containing alpha-H is easy to operate, aftertreatment is easy and convenient, substrate designability is strong, the compound of the needed structure can be designed and synthesized according to practical requirements, and practicability is strong. Meanwhile, the compound prepared through the method is good in biological activity, can be used as a raw material to synthesize a heterocyclic compound, and the economic value is high.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of an α-H-containing alkynyl imine compound. Background technique [0002] Alkynyl imine compounds are an important class of organic intermediates. A large number of studies have shown that the derivatives of alkynyl imines are highly active and can undergo a series of nucleophilic and electrophilic ring-closing reactions. important means. (Document I: From Acyliminiums / Amidoallenyliums to Highly Functionalized Allene Intermediates: Stereoselective Preparation of Z-Amidovinyl-Furans,-Pyrroles,-Thiophenes,-Benzofurans and-Benzothiophenes. Liu, L.; Chen, D.; Zhou, H. Adv. Synth. Catal. 2015, 357, 389. Literature II: Select fluor-Promoted Sequential Reactions via Allene Intermediates: Metal-Free Construction of Fused Polycyclic Skeletons. Liu, L.; Zhou, H.J. Org. Chem. DOI: 10.1021.). In addition, its unique double bond and triple bond alternate st...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/16C07C249/02
CPCC07C249/02C07C251/16C07C251/08
Inventor 周宏伟陈佃鹏姚金忠
Owner JIAXING UNIV
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