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1,4-diionic sulfur-containing ylide derivative based on asymmetric alkyne, and preparation method thereof

An ionic and asymmetric technology, applied in organic chemistry and other directions, can solve the problems of limiting the research value and application scope of ylide salts, and achieve the effects of good yield, easy amplification and easy availability of raw materials

Active Publication Date: 2019-08-09
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2011, Ayoob Bazgir's group reported the synthesis of a class of 1,4-diionic organic sulfur-containing onium salts (Moafi, L.; Ahadi, S.; Khavasi, H.R.; Bazgir, A. Three-Component Diastereoselective Synthesis of Stable 1,4-Diionic Organosulfurs, Synthesis2011,1399), but its research has great limitations, only studied the reaction of symmetrical butynedicarboxylates, because it is two identical ester groups, a great Limit the research value and application scope of the ylide

Method used

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  • 1,4-diionic sulfur-containing ylide derivative based on asymmetric alkyne, and preparation method thereof
  • 1,4-diionic sulfur-containing ylide derivative based on asymmetric alkyne, and preparation method thereof
  • 1,4-diionic sulfur-containing ylide derivative based on asymmetric alkyne, and preparation method thereof

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Experimental program
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Embodiment 1

[0022] The reaction formula of Example 1, the specifically used compound IV-1 and compound V-1 and the structure of the product I-1 are as follows.

[0023]

[0024] The specific experimental steps are: 791 mg (10 mmol, 1.0 equivalent) of compound II-1 and 320 mg (10 mmol, 1.0 equivalent) of compound III are dissolved in 50 mL of dichloromethane solvent, and 166 mg (10 mmol, 1.0 equivalent) of compound IV-1, naturally rose to room temperature, and reacted for 24 hours. After the reaction, the target compound I-1 can be obtained by suction filtration.

[0025] Product Ⅰ-1 is a yellow solid with a yield of 58%; melting point: 118-119°C. 1 H NMR (400MHz, d 6 -DMSO) δ9.00(d, J=5.6Hz, 2H), 8.74(t, J=7.6Hz, 1H), 8.24(t, J=7.2Hz, 2H), 4.18(q, J=7.2Hz, 2H), 1.23(t, J=7.1Hz, 3H); 13 C NMR (100MHz, d 6 -DMSO) δ168.84, 167.28, 149.66, 147.63, 128.92, 122.4(q, J=267.3Hz), 118.1(q, J=36.2Hz), 61.06, 13.93; ESI-HRMS m / z calcdfor C 11 h 10 f 3 NO 2 S+H + 278.0457,found 278.0453....

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Abstract

The main purpose of the present invention is to provide a 1,4-diionic sulfur-containing ylide derivative based on asymmetric alkyne, and a preparation method thereof. According to the present invention, with the method, the 1,4-diionic sulfur-containing ylide derivative based on asymmetric alkyne is simply and efficiently synthesized in one step from pyridine with different substituents, elementalsulfur and asymmetric internal alkyne by using dichloromethane as a reaction solvent. The invention further provides a preparation method of the compound.

Description

technical field [0001] The invention relates to a new class of asymmetric alkyne-based 1,4-diionic sulfur-containing ylide derivatives and a synthesis method thereof. Background technique [0002] Organic sulfur-containing compounds are closely related to people's lives, and have very important uses in pesticides, medicines, materials and even food. Therefore, many reagents for introducing sulfur into organic molecules have been developed. For example: traditional methods use mercaptans and thioethers to introduce sulfur atoms, but both mercaptans and thioethers have unpleasant odors, which limits their application; sulfur powder, inorganic sulfur salts, and some organic sulfur-containing small molecules have also been developed as sulfur atoms. source, but its development and application are relatively limited; and these methods mostly use transition metal catalyzed conditions. Due to the lack of current research (for example: foul smell, harsh conditions, metal catalysis...

Claims

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Application Information

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IPC IPC(8): C07D213/04C07D405/06C07D213/68
CPCC07D213/04C07D405/06C07D213/68
Inventor 程斌李运通翟宏斌张昕平李慧胡汉巍
Owner LANZHOU UNIVERSITY