3，3-二甲基-1-（1，2，4-三唑-1-基）-2-丁酮与仲胺和醛的一锅煮反应研究
摘要
为了研究一锅煮法合成3, 3-二甲基-1-(1, 2, 4-三唑-1-基)-2-丁酮(α-三唑基片呐酮)衍生物化合物的可行性并确定最佳反应条件,以对甲基苯甲醛、哌啶和3, 3-二甲基-1-(1, 2, 4-三唑-1-基)-2-丁酮为原料反应,考察了催化剂、溶剂、反应温度和时间对该反应的影响。并在试验确定的最佳反应条件下,用不同的原料合成出一系列新化合物,经IR、1H NMR确定了它们的化学结构,初步测定了它们对植物病菌的抑菌活性。主要结果如下:
以对甲基苯甲醛、仲胺和3, 3-二甲基-1-(1, 2, 4-三唑-1-基)-2-丁酮为原料研究的Mannich反应具有可行性。确定的最佳反应条件为:水作溶剂,无催化剂,35℃反应。在筛选出的最佳反应条件下,以醛、3, 3-二甲基-1-(1, 2, 4-三唑-1-基)-2-丁酮和仲胺为原料成功地合成了13个化合物,其中6个新化合物,经IR、1H NMR确定了它们的化学结构。
运用生长速率法测定了新化合物对4种植物病原菌的抑菌活性结果。表明,在质量浓度为100 mg/L条件下,化合物对这4种植物病原菌的菌丝生长均有不同程度的抑制作用。化合物c,e对马铃薯干腐病菌的抑制率均达到66.67%和78.33%;化合物f对小麦赤霉病菌的抑制率均达到69.23%;化合物c对棉花枯萎病菌的抑制率达到78.33% ;化合物f对小麦赤霉病菌有一定的促进生长作用。
The feasibility of one-pot three-component reaction of 3, 3- dimethyl-1-(1, 2, 4-triazole -1-yl)-2-butanone was studied and the best reaction conditions, including cayalists, solvent and tempreture were considered. A series of new compounds were synthesized under the best condition which was obtained by the previous works. The structures of these compounds were confirmed by IR, 1H NMR, and theirs melting points were determined. In order to study the relationship between structure and effect of these compounds, the antimicrobial activity to pathogens and bacteria were considered. The main results are as follows:
The Mannich type reaction of 3, 3- dimethyl-1-(1, 2,4-triazole-1-yl)-2-butanone, secondary amines and aldehydes reacted in aqueous media is feasible, and its best condition was 35℃in water .
Under this condition, 13 conpounds including 6 new compounds were synthesized using 3, 3- dimethyl-1-(1, 2,4-triazole-1-yl)-2-butanone, secondary amines and aldehydes, and their structures were determined by IR and 1H NMR.
The results inhibiting pathogenic fungi showed that the inhibitory rate of compounds c, e to Fusarium solani a were66.67%和78.33% at the concentration of 100mg/L; that of f to Fusarium graminearum was 69.23%; c, to Fusarium Cotton-wilt was78.33%. Compound f showed a promoting functions to Fusariumgraminearum.
以对甲基苯甲醛、仲胺和3, 3-二甲基-1-(1, 2, 4-三唑-1-基)-2-丁酮为原料研究的Mannich反应具有可行性。确定的最佳反应条件为:水作溶剂,无催化剂,35℃反应。在筛选出的最佳反应条件下,以醛、3, 3-二甲基-1-(1, 2, 4-三唑-1-基)-2-丁酮和仲胺为原料成功地合成了13个化合物,其中6个新化合物,经IR、1H NMR确定了它们的化学结构。
运用生长速率法测定了新化合物对4种植物病原菌的抑菌活性结果。表明,在质量浓度为100 mg/L条件下,化合物对这4种植物病原菌的菌丝生长均有不同程度的抑制作用。化合物c,e对马铃薯干腐病菌的抑制率均达到66.67%和78.33%;化合物f对小麦赤霉病菌的抑制率均达到69.23%;化合物c对棉花枯萎病菌的抑制率达到78.33% ;化合物f对小麦赤霉病菌有一定的促进生长作用。
The feasibility of one-pot three-component reaction of 3, 3- dimethyl-1-(1, 2, 4-triazole -1-yl)-2-butanone was studied and the best reaction conditions, including cayalists, solvent and tempreture were considered. A series of new compounds were synthesized under the best condition which was obtained by the previous works. The structures of these compounds were confirmed by IR, 1H NMR, and theirs melting points were determined. In order to study the relationship between structure and effect of these compounds, the antimicrobial activity to pathogens and bacteria were considered. The main results are as follows:
The Mannich type reaction of 3, 3- dimethyl-1-(1, 2,4-triazole-1-yl)-2-butanone, secondary amines and aldehydes reacted in aqueous media is feasible, and its best condition was 35℃in water .
Under this condition, 13 conpounds including 6 new compounds were synthesized using 3, 3- dimethyl-1-(1, 2,4-triazole-1-yl)-2-butanone, secondary amines and aldehydes, and their structures were determined by IR and 1H NMR.
The results inhibiting pathogenic fungi showed that the inhibitory rate of compounds c, e to Fusarium solani a were66.67%和78.33% at the concentration of 100mg/L; that of f to Fusarium graminearum was 69.23%; c, to Fusarium Cotton-wilt was78.33%. Compound f showed a promoting functions to Fusariumgraminearum.
引文
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[10] A. D?mling, Org. Chem. Highlights[J] 2004, April 5. Link
[11] Barton DHR: The invention of chemical reactions[M]. Aldrichimica Acta1990, 23:3.
[12] Seebach D: Organic chemistry: quo vadis[J]. Angew Chem 1990,102:1363-1409
[13] Dǒmling A , Ugi I. Multicomponent reactions with isocyanides[J ] . Angew Chem Int Ed ,2000 ,39 (18) :3168 - 3210.
[14] Ugi I. Glorious past and even more promising future.http :/ / www. mcr2000. org/ pdf/ ugi. pdf .
[15] Divanfard HR ,Lysenko Z ,Wang PC , et al . Synthesisof heterocyclic α-amino acid [ J ] . Synth Commun ,1978 ,8 (4) :269 - 273.
[16] Dǒmling A ,Ugi I. The seven-component reaction[J ] .Angew Chem Int Ed ,1993 ,32(4) :563 - 564.
[17] Keating TA ,Armstrong RW. Molecular diversity viaa convertible isocyanide in the Ugi four-componentcondensation[J ] . J Am Chem Soc , 1995 , 117 (29) :7842 - 7843.
[18] Weber L ,Wallbaum S ,Broger C , et al . Optimizationof the biological activity of combinatorial compoundlibraries by a genetic algorithm[J ] . Angew Chem IntEd ,1995 ,34 (20) :2280 - 2282.
[19] Weber L. The application of multicomponent reactions in drug discovery[J ] . Curr Med Chem ,2002 ,9(23) :2085 - 2093.
[20] Hulme C ,Gore V. multicomponent reactions :emerging chemistry in drug discovery ′from Xylocain toCrixivan′[ J ] . Curr Med Chem , 2003 , 10 (1) : 51 -80.
[21] Weber L. Multicomponent reactions and evolutionary chemistry[ J ] . Drug Discovery Today , 2002 , 7 ( 2) :143 - 147.
[22] Ugi I , Heck S. The multicomponent reactions and their libraries for natural and preparative chemistry [J ]. Combinatorial Chemistry & High Throughput Screening ,2001 ,4(1) :1 - 34.
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[39] L.Kuss, P. Karrer, Helv[J]. Chim. Acta, 1957(40):740.
[40] A. P. Phillips, J. Amer[J]. Chem. Soc., 1957(40):740.
[41] R. C. Elderfield[J]. Heterocyclic Compounds, 1950(1):462.
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