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Synthesis method of dehydroabietic-acid-based B ring-fused-thiazole-thiocarbamide compounds

A technology of dehydroabietic acid and compounds, applied in the direction of biocides, organic chemistry, chemicals for biological control, etc., can solve the problems that have not been reported at home and abroad, and achieve the effect of increasing added value

Active Publication Date: 2016-10-26
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The dehydroabietic acid-based B-cyclothiazole-thiourea compound of the present invention is a novel functional compound, and the material and its synthesis method have not been reported at home and abroad so far.

Method used

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  • Synthesis method of dehydroabietic-acid-based B ring-fused-thiazole-thiocarbamide compounds
  • Synthesis method of dehydroabietic-acid-based B ring-fused-thiazole-thiocarbamide compounds
  • Synthesis method of dehydroabietic-acid-based B ring-fused-thiazole-thiocarbamide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation of compound a:

[0026]

[0027] Into a 25mL two-necked flask, add 0.20g of dehydroabietyl B cyclothiazol-amine, 0.10g of phenylisothiocyanate and 5mL of acetonitrile, heat to reflux under stirring, react for 8h, and depressurize after the reaction is completed Acetonitrile was distilled off, and the residue was separated and purified by silica gel column chromatography. The eluent was ethyl acetate:petroleum ether=1:10 by volume to obtain compound a. m.p.175.0~176.0℃; IR(KBr,ν / cm -1 ):3149.22(ν N-H ), 2955.76, 2853.49 (ν Cα-H ),1726.96(ν C＝O ),1599.71(ν C＝S ), 1511.11, 1459.49 (ν Ar-C＝C ),1382.53(ν C-N ),1029.97(ν C-O-C ); 1 H NMR (600MHz, CDCl 3 )δ: 13.31 (s, 1H, Ph-NH), 9.98 (s, 1H, thizole-NH), 7.89 (s, 2H, H-Ph), 7.63 (d, J=1.5Hz, 1H, H-14 ),7.47(t,J=7.9Hz,2H,H-Ph),7.30(d,J=7.4Hz,1H,H-Ph),7.23(d,J=8.0Hz,1H,H-11), 7.19 (dd, J=8.0, 1.8Hz, 1H, H-12), 3.78 (s, 1H, H-5), 3.69 (s, 3H, COOCH 3 ),2.94(m,1H,H-15),2.34(d,J=9.3Hz,1H,H 1-e ),1.9...

Embodiment 2

[0029] Preparation of compound b

[0030]

[0031] Into a 25mL two-necked flask, add 0.20g of dehydroabietyl B cyclothiazol-amine, 0.11g of m-fluorophenyl isothiocyanate and 5mL of acetonitrile, heat to reflux under stirring, and react for 8 hours. Acetonitrile was distilled off under reduced pressure, and the residue was separated and purified by silica gel column chromatography. The eluent was ethyl acetate:petroleum ether=1:10 by volume to obtain compound b. m.p.187.0~188.0℃; IR(KBr,ν / cm -1 ):3155.81(ν N-H ),2954.44(ν Cα-H ),1727.40(ν C＝O ),1612.42(ν C＝S ), 1508.74, 1450.45 (ν Ar-C＝C ),1382.07(ν C-N ),1031.71(ν C-O-C ); 1 H NMR (600MHz, CDCl 3 )δ:13.53(s,1H,Ph-NH),10.48(s,1H,thizole-NH),7.95(s,1H,H-Ph),7.63(s,1H,H-14),7.58(s ,1H,H-Ph),7.40(dd,J=14.8,7.7Hz,1H,H-Ph),7.24(d,J=8.0Hz,1H,H-11),7.21(dd,J=8.0, 1.6Hz, 1H, H-12), 6.98(t, J=7.4Hz, 1H, H-Ph), 3.80(s, 1H, H-5), 3.73(s, 3H, COOCH 3 ),2.95(m,1H,H-15),2.35(d,J=6.0Hz,1H,H 1-e),1.89(m,5H,H-3,H-2,H 1-a ),1.63...

Embodiment 3

[0033] Preparation of compound c:

[0034]

[0035] Into a 25mL two-necked flask, add 0.20g of dehydroabietyl B cyclothiazol-amine, 0.11g of p-fluorophenylisothiocyanate and 5mL of acetonitrile, heat to reflux under stirring, and react for 8h. After the reaction is completed, Acetonitrile was distilled off under reduced pressure, and the residue was separated and purified by silica gel column chromatography. The eluent was ethyl acetate:petroleum ether=1:10 by volume to obtain compound c. m.p.191.0~192.0℃; IR(KBr,ν / cm -1 ):3280.93(ν N-H ),2951.97(ν Cα-H ),1713.10(ν C＝O ),1623.29(ν C＝S ), 1506.74, 1434.68 (ν Ar-C＝C ),1378.11(ν C-N ),1035.27(ν C-O-C )cm -1 ; 1 H NMR (600MHz, CDCl 3 )δ: 13.22 (s, 1H, Ph-NH), 10.01 (s, 1H, thizole-NH), 7.80 (s, 2H, H-Ph), 7.58 (d, J=1.6Hz, 1H, H-14 ),7.23(d,J=8.0Hz,1H,H-11),7.20(dd,J=8.0,1.8Hz,1H,H-12),7.16(t,J=8.6Hz,2H,H-Ph ),3.79(s,1H,H-5),3.69(s,3H,COOCH 3 ),2.94(dq,J=13.8,6.9Hz,1H,H-15),2.34(d,J=5.9Hz,1H,H 1-e ),1.94–1.80(m,5H...

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Abstract

The invention relates to a synthesis method of dehydroabietic-acid-based B ring-fused-thiazole-thiocarbamide compounds. The method comprises the following steps: preparing methyl dehydroabietate from dehydroabietic acid, oxidizing in an acetic acid-acetic anhydride mixed solution with CrO3 to obtain methyl 7-carbonyl dehydroabietate, carrying out reaction on the methyl 7-carbonyl dehydroabietate and bromine in acetic acid to generate methyl 6-bromo-7-carbonyldehydroabietate, carrying out reaction on the methyl 6-bromo-7-carbonyldehydroabietate and thiocarbamide in acetic acid to obtain a dehydroabietic-acid-based B ring-fused-thiazole-amine intermediate, and carrying out reaction on the dehydroabietic-acid-based B ring-fused-thiazole-amine intermediate and a series of isorhodanates to obtain the dehydroabietic-acid-based B ring-fused-thiazole-thiocarbamide compounds. The invention implements synthesis of the dehydroabietic-acid-based B ring-fused-thiazole-thiocarbamide compounds for the first time. The antibacterial activity test indicates that the dehydroabietic-acid-based B ring-fused-thiazole-thiocarbamide compounds have certain antibacterial activities and widen the application range of dehydroabietic acid. The dehydroabietic acid is a component of the natural product rosin, so the preparation method is simple and is low in cost.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of a novel functional compound based on dehydroabietic acid, thiazole and thiourea——dehydroabietic acid-based B-cyclothiazole-thiourea compound. Background technique [0002] Thiazole compounds widely exist in many natural products and bioactive molecules, and exhibit a wide range of biological activities such as antibacterial, herbicidal, anticancer and antiviral. Thiourea compounds also exhibit a wide range of biological activities, such as antibacterial, herbicidal, insecticidal, regulating plant growth, antitumor, etc. At present, most of these two types of compounds show the advantages of low toxicity to the human body, so they are widely used in the fields of pesticides and medicine, and are worthy of further research, so as to develop more and more effective drugs. [0003] Rosin is a renewable natural resource. my country is the country with...

Claims

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Application Information

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IPC IPC(8): C07D277/60A01P3/00
CPCC07D277/60
Inventor 段文贵陈乃源岑波林桂汕刘陆智
Owner GUANGXI UNIV
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