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Synthesis and uses of beta-1-imidazole-2,3,4,6-tetrasulfo-D-glucopyranose hydrosulfate

A technology of glucopyranose and hydrogen sulfide, applied in the field of multi-component reaction chemical synthesis of hydrogen sulfide, which can solve the problems of difficult control of reaction selectivity, increase of reactant types, increase of reactive sites, etc., and achieve high Practical application value, short reaction time, and the effect of reflecting green environmental protection

Active Publication Date: 2015-07-08
江西省德兴市百勤异VC钠有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide a kind of synthesis and application of β-1-imidazole-2,3,4,6-tetrasulfonic acid-D-glucopyranose thiohydrogenate, to solve the problem of reactants in the prior art. With the increase of species, the number of reactive sites increases, the selectivity of the reaction is difficult to control, and it is difficult to generate a main product with high selectivity and high yield.

Method used

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  • Synthesis and uses of beta-1-imidazole-2,3,4,6-tetrasulfo-D-glucopyranose hydrosulfate
  • Synthesis and uses of beta-1-imidazole-2,3,4,6-tetrasulfo-D-glucopyranose hydrosulfate
  • Synthesis and uses of beta-1-imidazole-2,3,4,6-tetrasulfo-D-glucopyranose hydrosulfate

Examples

Experimental program
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Effect test

Embodiment 1

[0061] Embodiment 1: Taking 3-hydroxyl-3-(2-oxo-2-phenylethyl)indol-2-one (10a) as an example:

[0062] Aryl formaldehyde 7a (2mmol), p-methylaniline 8a (2mmol), ethyl acetoacetate 9 (1mmol), catalyst 6 (10mol%) and ethanol (2mL) were sequentially added to a 50mL round-bottomed flask, mixed well, 40 The reaction was complete at ℃ (TLC tracking), cooled the system to room temperature, added 20 mL of distilled water, stirred until a solid precipitated, filtered with suction, and recrystallized (95% EtOH-DMF=1:4) to obtain the product 10a.

[0063] Ethyl 4-(4-tolylamino)-1,2,5,6-tetrahydro-2,6-diphenyl-1-(4-tolylpyridine)-3-carbox ylate(19a)

[0064] 7.28-7.31(m,8H),10.18(s,1H); 13 C NMR (100MHz, CDCl 3 ): δ168.3, 156.4, 144.9, 144.4, 143.1, 135.5, 135.2, 129.5, 129.4, 128.6, 128.2, 127.0, 126.7, 126.5, 126.2, 125.9, 125.0, 112.9, 95.6, 59.6, 08.2, 2 20.1, 14.8; HRMS(ESI) m / z: calc.for C 34 h 34 N 2 o 2 Na[M+Na] + found(expected):525.2513(525.2518)..

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Abstract

The invention relates to synthesis and uses of beta-1-imidazole-2,3,4,6-tetrasulfo-D-glucopyranose hydrosulfate and belongs to hydrosulfate chemical synthesis by multi-component reactions and uses of the hydrosulfate. The synthesis includes: subjecting glucose 1 that is adopted as a raw material to acetylation to obtain a compound 2; performing bromination by adopting the compound 2 as a raw material to obtain a compound 3; reacting the compound 3 with 1-methylimidazole to obtain a compound 4; hydrolyzing the compound 4 under alkaline conditions to obtain a target compound 5; and reacting the compound 5 with chlorosulfonic acid to obtain a target product 6 that is the beta-1-imidazole-2,3,4,6-tetrasulfo-D-glucopyranose hydrosulfate. A five-component reaction of 2 equivalents of an aromatic aldehyde, 2 equivalents of an arylamine and 1 equivalent of ethyl acetoacetate is performed by adopting the target product 6 as a catalyst at 40 DEG C under mild conditions to synthesize an ethyl 4-phenylamino-1-phenyl-1,2,5,6-tetrahydro-2,6-diphenylpyridine-3-carboxylate derivative. The synthesis and the uses are characterized in that: (1) the product 10 is obtained rapidly with a high yield; (2) reaction conditions are mild, operation is simple, reaction time is short, the yield is high and after-treatment is simple and convenient; and (3) the synthesis is green, economical and efficient.

Description

technical field [0001] The present invention relates to a multi-component reaction chemical synthesis of hydrogen sulfide and its application, especially a kind of β-1-imidazole-2,3,4,6-tetrasulfonic acid group-D-glucopyranose sulfuric acid Synthesis and use of salt. Background technique [0002] Multi-component reactions have received more and more attention in chemical synthesis, but with the increase of reactant species, the number of reactive sites increases. If the catalyst activity is not high, the selectivity of the reaction will be difficult to control, and it is difficult to achieve high selectivity. , generate a main product with a high yield, so most of the multi-component reactions that have been reported so far are three or four-component reactions, and the relevant reports of multi-component reactions with more than four components are rare. There are several articles. [0003] Pentasubstituted tetrahydropyridine derivatives are an important class of nitrogen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/052C07H1/00B01J31/02C07D211/78
CPCB01J31/0229C07D211/78C07H1/00C07H19/052
Inventor 宛瑜张潇潇王超周秋菊张莉卓邹欢吴翚
Owner 江西省德兴市百勤异VC钠有限公司
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