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New method of synthesizing 1, 2, 3-triazol 1, 3-diazacyclo compound

A technology for a diazide heterocycle and a synthesis method, which is applied in 1 field, can solve the problems of inability to meet high-throughput screening and drug research and development, and achieve the effects of achieving molecular diversity, high yield and simple route.

Inactive Publication Date: 2009-09-30
YUNNAN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] And the known synthetic method of this class compound needs to use poisonous, unpleasant raw material (as p-toluenesulfonyl chloride), needs multi-step reaction simultaneously (needs to be prepared p-toluenesulfonyl azide by p-toluenesulfonyl chloride at first) just can complete synthetic
Obviously, traditional synthetic methods can no longer meet the requirements of high-throughput screening and drug research and development, so it is particularly important to establish an efficient, concise and parallel method for synthesizing such compounds

Method used

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  • New method of synthesizing 1, 2, 3-triazol 1, 3-diazacyclo compound

Examples

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Embodiment 1

[0031] Example 1: Synthesis of 4-acetyl-1,2,3-triazol[1,5e]tetrahydroimidazole (I-A): 10 milliliters of dry DMF was added successively in a 25 milliliter round bottom flask, 2, 4, 0.53 g (2 mmol) of 5,6-tetrachloro-1,3-isophthalonitrile, 0.26 g (4 mmol) of sodium azide, stirred with a magnetic stirrer for 1 hour, and detected by TLC 2, 4, 5 , 6-1,3-isophthalonitrile reacted completely. Add 0.25 gram (2 millimoles) 2-acetylmethylenetetrahydroimidazoles in this reaction bottle again, continue to stir after 10 hours, TLC detects that 2-acetylmethylenetetrahydroimidazoles reacts completely, stop reaction, use After washing with 20 milliliters of water, extract with ethyl acetate, collect the organic layer and dry it with anhydrous sodium sulfate, remove ethyl acetate under reduced pressure, dissolve and mix silica gel with acetone, put it on the column by dry method, use eluent (ethyl acetate: petroleum Ether = 1:1) to obtain white crystals with a yield of 85-89% and a melting po...

Embodiment 2

[0034] Example 2: Synthesis of 4-acetyl-1,2,3-triazol[1,5e]tetrahydroimidazole (I-A): 10 milliliters of dry DMF, 5-chloro- 2,4,6-trifluoro-1,3-isophthalonitrile 0.43 g (2 mmol), sodium azide 0.26 g (4 mmol), magnetic stirrer for 1 hour, TLC detection 2,4 , 5,6-1,3-isophthalonitrile reacted completely. Add 0.25 gram (2 millimoles) 2-acetylmethylenetetrahydroimidazoles in this reaction bottle again, continue to stir after 10 hours, TLC detects that 2-acetylmethylenetetrahydroimidazoles reacts completely, stop reaction, use After washing with 20 ml of water, extract with ethyl acetate, collect the organic layer and dry it with anhydrous sodium sulfate, remove the ethyl acetate under reduced pressure, dissolve it with acetone and mix with silica gel, put it on the column by dry method, and use eluent (ethyl acetate: petroleum Ether = 1:1) eluted to give white crystals with a yield of 80%.

Embodiment 3

[0035] Example 3: Synthesis of 4-acetyl-1,2,3-triazol[1,5e]tetrahydroimidazole (I-A): 10 milliliters of dry DMF was added successively in a 25 milliliter round bottom flask, 2, 4, 0.40 g (2 mmol) of 5,6-tetrafluoro-1,3-isophthalonitrile, 0.26 g (4 mmol) of sodium azide, stirred with a magnetic stirrer for 1 hour, TLC detection 2, 4, 5 , 6-1,3-isophthalonitrile reacted completely. Add 0.25 gram (2 millimoles) 2-acetylmethylenetetrahydroimidazoles in this reaction bottle again, continue to stir after 10 hours, TLC detects that 2-acetylmethylenetetrahydroimidazoles reacts completely, stop reaction, use After washing with 20 ml of water, extract with ethyl acetate, collect the organic layer and dry it with anhydrous sodium sulfate, remove the ethyl acetate under reduced pressure, dissolve it with acetone and mix with silica gel, put it on the column by dry method, and use eluent (ethyl acetate: petroleum Ether = 1:1) eluted to give white crystals with a yield of 87%.

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Abstract

The invention discloses a new method of synthesizing a 1, 2, 3-triazol 1, 3-diazacyclo compound with pharmaceutical activity. The structure of the 1, 2, 3-triazol 1, 3-diazacyclo compound with pharmaceutical activity is shown in figure (1), wherein n is equal to 1, 2 or 3; z is an O atom, an S atom or NR'; R' is a hydrogen atom, methyl, nitryl, cyano, amido, C[1-8]alkyl, C[1-8]alkylamino, C[1-8]alkanoyl, aroyl, dense aroyl, aryl, dense aryl, naphthenic base, aralkyl, oxa-alkyl, oxa-acyl, thia-alkyl or thia- acyl; R is alkyl, aryl, substituted aryl or heterocyclic aryl; n is equal to 1, 2 or 3; Z is an O atom, an S atom or NH preferably; and R is methyl, phenyl, p-methylphenyl, p-chlorphenyl or p-methoxyphenyl preferably. The invention is characterized in that, substituted halobenzene, hydrazoates and heterocyclic ketene amines or derivatives thereof are used for preparing the 1, 2, 3-triazol 1, 3-diazacyclo compound which has pharmaceutical activity and has the structure shown in figure (1) at high yield by the one kettle way. The invention has the advantages of simple synthesizing technology, moderate conditions and high yield. The invention achieves the synthesis of heterocyclic compound libraries at high yield in a parallel mode by the one kettle way, and really achieves molecular multiformity. In addition, the invention has the characteristics of high yield, simple lines, moderate conditions and the like.

Description

technical field [0001] The invention relates to a new method for synthesizing 1,2,3-triazolo-1,3-diazaheterocyclic compounds with pharmaceutical activity. Background technique [0002] 1,2,3-triazolo 1,3-diazaheterocyclic compounds have anti-tumor (Yu Chuyi, Yuan Xuening, Zhao Meixin, Huang Zhitang Chinese invention patent: Publication No. CN101153041), bacteria, fungi and other outstanding biological Active, and has broad-spectrum, high-efficiency, long-acting. The research on 1,2,3-triazoloheterocyclic compounds is one of the hotspots in the field of drug research at present. The reason is that among natural and synthetic fungicides with physiological activity, a considerable number of compounds have 1 , 2,3-triazoloheterocyclic skeleton structure. [0003] However, the known synthetic methods of this type of compound need to use toxic and unpleasant raw materials (such as p-toluenesulfonyl chloride), and multi-step reactions (need to first prepare p-toluenesulfonyl azid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D498/04
Inventor 林军刘永江严胜骄陈育兰刘琳
Owner YUNNAN UNIV
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