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Imidazo heterocyclic amino dithiocarbamate and preparation method therefor

A technology of cyclic carbamodithiocarbamate and imidazolo, which is applied in the field of organic chemical synthesis, can solve the problem that no carbamodithiocarbamate fragments are introduced into imidazo heterocycles, etc., and achieve good research value and application prospects , mild reaction conditions, and easy-to-obtain raw materials

Active Publication Date: 2015-12-09
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no technical method for introducing carbamate fragments into imidazoheterocycles (including imidazopyridine and imidazothiazole, etc.)

Method used

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  • Imidazo heterocyclic amino dithiocarbamate and preparation method therefor
  • Imidazo heterocyclic amino dithiocarbamate and preparation method therefor
  • Imidazo heterocyclic amino dithiocarbamate and preparation method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 12

[0037] Synthesis of embodiment 12-phenylimidazole-[1,2-a]pyridin-3-yl-dimethylamino-dithiocarbamate

[0038] The synthetic route is:

[0039]

[0040] Specifically include the following steps:

[0041] The above formula (a) compound, formula (b) compound, iron trifluoride, and iodine simple substance are made to have a molar ratio of 1:1:0.05:0.2, wherein the formula (a) compound is 2 mmol. The reaction system was stirred and reacted at 80° C. for 3 hours. Cool after the reaction, filter with short silica gel column, and rotate the filtrate to remove excess iodine, remove the solvent, use silica gel column chromatography, wash with petroleum ether, detect by TLC, combine the effluent containing the product, and use a rotary evaporator The solvent was distilled off and dried in vacuo to obtain the target product as a yellow solid with a yield of 74% and a purity of 99.1% (HPLC).

[0042] NMR spectroscopy:

[0043] 1 HNMR (500MHz, CDCl 3 )δ8.17–8.15(m,1H),7.90(d,J=8.0Hz,2...

Embodiment 26

[0045] Synthesis of Example 26-methyl-2-phenylimidazole-[1,2-a]pyridin-3-yl-dimethylamino-dithiocarbamate

[0046] synthetic route:

[0047]

[0048] Specifically include the following steps:

[0049] The above formula (a) compound, formula (b) compound, iron trifluoride, and iodine simple substance are made to have a molar ratio of 1:1:0.05:0.2, wherein the formula (a) compound is 2 mmol. The reaction system was stirred and reacted at 80° C. for 3 hours. Cool after the reaction, filter with short silica gel column, and rotate the filtrate to remove excess iodine, remove the solvent, use silica gel column chromatography, wash with petroleum ether, detect by TLC, combine the effluent containing the product, and use a rotary evaporator The solvent was distilled off and vacuum-dried to obtain the target product as a yellow liquid with a yield of 76% and a purity of 99.3% (HPLC).

[0050] NMR spectroscopy:

[0051] 1 HNMR (500MHz, CDCl 3 )δ8.00–7.98(m,2H),7.94(s,1H),7.61(...

Embodiment 32

[0053] Synthesis of Example 32-methylimidazole-[1,2-a]pyridin-3-yl-dimethylamino-dithiocarbamate

[0054] The synthetic route is:

[0055]

[0056] Specifically include the following steps:

[0057] The above formula (a) compound, formula (b) compound, iron trifluoride, and iodine simple substance are made to have a molar ratio of 1:1:0.05:0.2, wherein the formula (a) compound is 2 mmol. The reaction system was stirred and reacted at 80° C. for 3 hours. Cool after the reaction, filter with short silica gel column, and rotate the filtrate to remove excess iodine, remove the solvent, use silica gel column chromatography, wash with petroleum ether, detect by TLC, combine the effluent containing the product, and use a rotary evaporator The solvent was distilled off and vacuum-dried to obtain the target product as a yellow liquid with a yield of 41% and a purity of 99.3% (HPLC).

[0058] NMR spectroscopy:

[0059] 1 HNMR (500MHz, CDCl 3 )δ8.08(d, J=6.5Hz, 1H), 7.59(d, J=9....

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PUM

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Abstract

The invention discloses imidazo heterocyclic amino dithiocarbamate and a preparation method therefor. The structural formula is shown in the description. In the presence of a lewis acid catalyst and an iodine reagent, a reaction on an imidazo heterocyclic compound and dialkyl amino dithio compound in a reaction solvent so as to prepare target amino dithiocarbamate imidazo heterocyclic compound. The method disclosed by the invention in one-step reactive synthesis is simple to operate and is mild in reaction condition, raw materials are cheap and easily available, and the method has a good market application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and specifically relates to an imidazoheterocyclic aminodithiocarbamate and a preparation method thereof. Background technique [0002] Imidazopyridine is an excellent drug lead skeleton with outstanding biological activity. People have created a variety of drugs based on imidazoheterocyclic skeleton. For example, the anti-anxiety and anti-psychotic drugs Alpidem, Zolpidem, and Saripidem, the anti-ulcer and gastric reflux drug Zolimidine, and osteoarthritis Loosening drug minodronic acid (minodronic acid), anti-HIV drug GSK812397 and so on. [0003] Therefore, functionalization reactions based on imidazopyridine skeletons have attracted extensive interest. For example, a variety of imidazopyridine-based arylation, sulfidation, olefinylation, carbonylation, and trifluoromethylation reactions have been developed. However, no technical method for introducing a carbamate moiety ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D513/04
CPCC07D471/04C07D513/04
Inventor 汤日元焦婧徐莉颜芸
Owner SOUTH CHINA AGRI UNIV
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