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A kind of synthetic method of n-aminoethyl terpinene maleimido imidazole derivative

A technology of enemaleimide imidazole and aminoethyl terpine, which is applied in the field of synthesis of N-aminoethyl terpinene maleimide imidazole derivatives, can solve problems that have not been reported at home and abroad. and other issues to achieve the effect of increasing added value

Active Publication Date: 2016-01-27
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The N-aminoethylterpinene maleimidazole derivative of the present invention is a new type of functional derivative, and the substance and its synthesis method have not been reported at home and abroad so far.

Method used

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  • A kind of synthetic method of n-aminoethyl terpinene maleimido imidazole derivative
  • A kind of synthetic method of n-aminoethyl terpinene maleimido imidazole derivative
  • A kind of synthetic method of n-aminoethyl terpinene maleimido imidazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation of compound a:

[0024]

[0025] Add 0.6gATM, 0.4g benzil, 0.26g benzaldehyde, 1.5gNH to the three-necked flask 4 OAc, 0.032gZnO and 5ml toluene, stirred and refluxed for 2h, ended the reaction when there was no ATM detected by TLC and ninhydrin, evaporated the solvent, purified the crude product with a silica gel column, and the eluent was petroleum ether / ethyl acetate: 10 / 1, 5 / 1, 3 / 1 gradient elution, and then recrystallized from a mixed solution of dichloromethane and petroleum ether to obtain the target product a. White crystal, m.p.187~188℃. IR(KBr,cm -1 ) ν: 3030 (Ar-H), 2958, 2869 (C-H), 1771, 1700 (C=O), 1601 (Ar-C=C), 1502 (C=N), 1125 (C-N). 1 HNMR (600MHz, CDCl 3 )δ / ppm: 7.73~7.71(m,2H,C 19 -H,C 23 -H),7.52~7.49(m,5H,C b1 -H,C c1 -H,C d1 -H,C e1 -H,C f1 -H),7.49~7.46(m,4H,C 20 -H,C 22 -H,C b -H,C f -H),7.45(t,J=7.4Hz,1H,C 21 -H),7.19(t,J=7.5Hz,2H,C c -H,C e -H),7.13(t,J=7.3Hz,1H,C d -H),5.74(d,J=8.4Hz,1H,C 8 -H),5.66(d,J...

Embodiment 2

[0027] Preparation of compound b:

[0028]

[0029] Add 0.6gATM, 0.4g benzil, 0.3g p-fluorobenzaldehyde, 1.5gNH 4OAc, 0.032gZnO and 5ml toluene, stirred and refluxed for 2h, ended the reaction when there was no ATM detected by TLC and ninhydrin, evaporated the solvent, purified the crude product with a silica gel column, and the eluent was petroleum ether / ethyl acetate: 10 / 1, 5 / 1, 3 / 1 gradient elution, and then recrystallized from a mixed solution of dichloromethane and petroleum ether to obtain the target product b. Pale yellow powder, m.p.212~214℃. IR(KBr,cm -1 ) ν: 3030 (Ar-H), 2958, 2869 (C-H), 1771, 1700 (C=O), 1601 (Ar-C=C), 1529 (C=N), 1107 (C-N). 1 HNMR (600MHz, CDCl 3 )δ / ppm: 7.73(m,2H,C 19 -H,C 23 -H),7.50(m,5H,C b1 -H,C c1 -H,C d1 -H,C e1 -H,C f1 -H),7.47~7.44(m,2H,C b -H,C f -H),7.21(m,2H,C 20 -H,C 22 -H),7.19(m,2H,C c -H,C e -H),7.13(t,J=7.3Hz,1H,C d -H),5.76(d,J=8.4Hz,1H,C 8 -H),5.67(d,J=8.4Hz,1H,C 7 -H),4.13(dt,J=14.0,6.8Hz,1H,C 16 -H a...

Embodiment 3

[0031] Preparation of compound c:

[0032]

[0033] Add 0.6gATM, 0.4g benzil, 0.26g o-fluorobenzaldehyde, 1.5gNH 4 OAc, 0.032gZnO and 5ml toluene, stirred and refluxed for 2h, ended the reaction when there was no ATM detected by TLC and ninhydrin, evaporated the solvent, purified the crude product with a silica gel column, and the eluent was petroleum ether / ethyl acetate: 10 / 1, 7 / 1, 5 / 1, 3 / 1, 2 / 1 gradient elution, and then recrystallized with a mixed solution of dichloromethane and petroleum ether to obtain the target product c. Pale yellow powder, m.p.65~68℃. IR(KBr,cm -1 ) ν: 3039 (Ar-H), 2958, 2869 (C-H), 1771, 1700 (C=O), 1601 (Ar-C=C), 1580 (C=N), 1017 (C-N). 1 HNMR (600MHz, CDCl 3 )δ / ppm:7.71(td,J=7.5,1.7Hz,1H,C 23 -H),7.51(dd,J=7.3,6.0Hz,5H,C b1 -H,C c1 -H,C d1 -H,C e1 -H,C f1 -H),7.49~7.48(m,2H,C b -H,C f -H),7.47(m,1H,C 21 -H),7.31(td,J=7.5,0.9Hz,1H,C 20 -H),7.21(m,1H,C 22 -H),7.18(d,J=7.7Hz,2H,C c -H,C e -H),7.13(t,J=7.3Hz,1H,C d -H),5.75(d,J=8....

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Abstract

The invention provides a synthesis method of an N-aminoethyl terpinene maleimido imidazole derivative. The synthesis method comprises the following steps: converting alpha-pinene serving as a raw material into alpha-terpinene maleic anhydride adduct (called TMA for short), then reacting the alpha-terpinene maleic anhydride adduct with ethanediamine so as to prepare a midbody, namely N-aminoethyl terpinene maleimide (called ATM for short), and then synthesizing the N-aminoethyl terpinene maleimido imidazole derivative with potential biological activity through modified reaction of amino in the N-aminoethyl terpinene maleimide. The synthesis method has the advantages that the synthesis of the important imidazole ring-containing organic compound by introducing N atoms into the alpha-terpinene maleic anhydride structure is realized for the first time; the N-aminoethyl terpinene maleimido imidazole compound has multiple biological activity, particularly bactericidal activity, the applicant range of the alpha-pinene is widened, and a new approach is supplied for the deep development and utilization of natural organic green resources-turpentine.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing N-aminoethylterpinene maleimidazole derivatives. Background technique [0002] As active center functional groups of many natural enzymes and biological systems, imidazoles play important roles in the fields of medicine and pesticides. In the field of medicine, some imidazole compounds have antibacterial, anticancer, anti-inflammatory, analgesic, anti-allergic and other drug activities. In the field of pesticides, many imidazole-based compounds can be used as fungicides, enzyme inhibitors, insecticides, plant growth regulators and herbicides. Imidazole compounds have attracted the attention of many scientists because of their high efficiency, low toxicity, low resistance to drug resistance and environmental friendliness. In recent years, imidazole derivatives have become a research hotspot in the synthesis and application of new nitrogen-cont...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/06A01P3/00
CPCC07D403/06
Inventor 段文贵蔺志铎岑波林桂汕刘陆智
Owner GUANGXI UNIV
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