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Preparation method for Mannich base containing ferrocenyl thiadiazole or oxadiazole

A technology based on thiadiazolyl and oxadiazolyl is applied in the field of preparation of ferrocene-based thiadiazole or oxadiazolyl-based Mannich base, and can solve the problem that catalysts pollute the environment, are difficult to recycle, and have low catalytic efficiency. and other problems, to achieve the effect of simple post-processing, simple operation and low reaction cost

Inactive Publication Date: 2020-02-07
SHAANXI UNIV OF SCI & TECH
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Problems solved by technology

The existing methods for the preparation of ferrocenyl-thiadiazole or oxadiazolyl-based Mannich bases generally use concentrated hydrochloric acid, aluminum trichloride, acetic acid, etc. to catalyze the synthesis. The above processes have catalysts that pollute the environment, have low catalytic efficiency, and are not easy to recycle. Disadvantages such as utilization and high cost

Method used

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  • Preparation method for Mannich base containing ferrocenyl thiadiazole or oxadiazole
  • Preparation method for Mannich base containing ferrocenyl thiadiazole or oxadiazole
  • Preparation method for Mannich base containing ferrocenyl thiadiazole or oxadiazole

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Example 1 Preparation of 1-(5'-phenyl-1',3',4'-thiadiazole-2'-amino)-ethyl-ferrocenyl ketone

[0035] Add 2-amino 5-phenyl-1,3,4-thiadiazole (1mol), 37% formaldehyde (5mol) solution to a dry three-necked flask, and absolute ethanol as a solvent, stir well; add benzothiazolium ion liquid (1.2mol), then slowly add acetylferrocene (1mol) absolute ethanol solution dropwise, and heat to reflux until the reaction ends (monitored by TLC), evaporate the solvent under reduced pressure, add ethyl acetate to the residue, Suction filtration, the filter cake is benzothiazole ionic liquid, which can be recycled and reused; the filtrate filtrate is evaporated to dryness to obtain the crude product, which is recrystallized from absolute ethanol to obtain 1-(5'-phenyl-1',3',4' -Thiadiazole-2'-amino)-ethyl-ferrocenyl ketone, m.p.196-198°C, yield: 91.8%.

[0036] IR(KBr)v:3324(ν Ph-H ),2914(ν 饱和C -H),1730(ν C＝O ),1611(ν C＝C ),1365(ν C-N ),806(γ 1,4-Ph-H ).

[0037] 1 HNMR(DMSO,40...

Embodiment 2

[0039] Example 2 Preparation of 1-(5'-p-chlorophenyl-1',3',4'-thiadiazole-2'-amino)-ethyl-ferrocenyl ketone

[0040]Add 2-amino 5-p-chlorophenyl-1,3,4-thiadiazole (1mol) and 37% formaldehyde (5mol) solution to a dry three-necked flask, and use absolute ethanol as a solvent, stir well; add benzo Thiazole ionic liquid (1.2mol), then slowly add acetyl ferrocene (1mol) absolute ethanol solution dropwise, heat and reflux until the end of the reaction (monitored by TLC), evaporate the solvent under reduced pressure, and add ethyl acetate to the residue Ester, suction filtration, the filter cake is benzothiazole ionic liquid, which can be recycled and reused; the filtrate is evaporated to dryness to obtain the crude product, which is recrystallized from absolute ethanol to obtain 1-(5'-p-chlorophenyl-1',3' ,4'-thiadiazole-2'-amino)-ethyl-ferrocenyl ketone, m.p.170-172°C, yield: 90.8%.

[0041] IR(KBr)v:3310(ν Ph-H ),2999(ν 饱和C-H ),1708(ν C＝O ),1600(ν C＝C ),1320(ν C-N ),774(γ 1...

Embodiment 3

[0044] Example 3 Preparation of 1-(5'-p-nitrophenyl-1',3',4'-thiadiazole-2'-amino)-ethyl-ferrocenyl ketone

[0045] Add 2-amino 5-p-nitrophenyl-1,3,4-thiadiazole (1mol) and 37% formaldehyde (5mol) solution in a dry three-necked flask, and dehydrated alcohol is used as a solvent, stir well; add benzene and thiazole ionic liquid (1.2mol), then slowly add acetyl ferrocene (1mol) absolute ethanol solution dropwise, and heat to reflux until the end of the reaction (monitored by TLC), evaporate the solvent under reduced pressure, and add acetic acid to the residue Ethyl ester, suction filtration, the filter cake is benzothiazole ionic liquid, which can be recycled and reused; the filtrate is evaporated to dryness to obtain the crude product, which is recrystallized from absolute ethanol to obtain 1-(5'-p-nitrophenyl-1', 3',4'-Thiadiazole-2'-amino)-ethyl-ferrocenyl ketone. m.p. 199-201°C, yield: 92.3%.

[0046] IR(KBr)v:3288(ν Ph-H ),2994(ν 饱和C-H ), 1759 (ν C＝O ),1600(ν C＝C ),1...

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Abstract

The invention provides a preparation method for a Mannich base containing ferrocenyl thiadiazole or oxadiazole. The method comprises the following steps: sequentially adding A mol of 2-amino-5-substituted-1,3,4-thia(oxa)diazole, B mol of an aldehyde and absolute ethanol into a dry three-necked flask, and performing uniform stirring; and adding C mol of a benzothiazole ionic liquid, slowly adding Dmol of an acetylferrocene anhydrous ethanol solution dropwise under stirring, after addition is completed, performing a reflux reaction under heating until the reaction is completed, performing reduced-pressure distillation to remove a solvent, adding ethyl acetate into residues, performing suction filtration, performing evaporation on the filtrate to dryness to obtain a crude product, and performing recrystallization on the crude product by using anhydrous ethanol to obtain the Mannich base containing the ferrocenyl thiadiazole or oxadiazole, wherein the filter cake is a benzothiazole ionicliquid and can be recycled and reused, and the ratio of the A to the B to the C to the D is 1:(5-10):(0.5-1.5):1. The method provided by the invention is environmentally friendly, and simple and convenient to operate, and has simple after-treatment, a high yield, and high efficiency, the catalyst can be recycled for multiple times, and the reaction costs are low.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a preparation method of a ferrocenyl thiadiazole or oxadiazolyl Mannich base Background technique [0002] Mannich reaction is an effective way to synthesize C-N bonds and C-C bonds. The Mannich reaction can introduce aromatic rings, heterocycles, unsaturated groups, etc. into Mannich bases, which greatly broadens the application of Mannich bases. For example, the medical fields such as antibacterial drugs, anti-tuberculosis drugs, anticonvulsants, and antiproliferative drugs, the fields of materials such as polyurethane materials and corrosion-resistant agents, and the biological fields such as regulating cellular immunity all involve Mannich bases. The Mannich base synthesized by introducing thia(oxa)diazole into the derivatives of ferrocene has a good application prospect. Because ferrocene derivatives can be used as catalysts due to their special spatial structur...

Claims

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Application Information

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IPC IPC(8): C07F17/02B01J31/02
CPCB01J31/0284B01J31/0285C07F17/02Y02P20/584
Inventor 尹大伟邹倩刘玉婷
Owner SHAANXI UNIV OF SCI & TECH
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