氮杂吡咯西里啶类化合物的合成及抗菌活性  

Synthesis and Antifungal Activity of Azapyrrolizidines

作　　者：吴璐璐[1] 杨国玉[1] 江圣飞 樊小改 徐翠莲[1] WU Lu-lu;YANG Guo-yu;JIANG Sheng-fei;FAN Xiao-gai;XU Cui-lian(College of Sciences,Henan Agricultural University,Zhengzhou 450002,China)

机构地区：[1]河南农业大学理学院,河南郑州450002

出　　处：《化学试剂》2024年第1期91-97,共7页Chemical Reagents

基　　金：河南省科技攻关项目(232102310379);河南农业大学自然科学类青年创新基金项目(KJCX2020A19)。

摘　　要：在乙内酰脲、醛和丙二腈为原料,锌为催化剂的条件下,一锅法得到氮杂吡咯西里啶衍生物,尝试不同取代的醛,得到17种目标化合物,产率为40%~94%。结果表明,以水为溶剂,温度为80℃,锌催化剂用量为10%为最优反应条件。产物结构经红外光谱(IR)、核磁共振波谱(NMR)和高分辨质谱(HRMS)确证。该方法具有反应条件温和、溶剂无毒、后处理简单、产率高、催化剂可循环使用等优点。采用菌丝生长法测试了其对禾谷镰刀菌、串珠镰刀菌、尖孢镰刀菌、烟草疫霉菌和立枯丝核菌的抗菌活性。结果表明,目标化合物对供试病原菌均有一定的抑菌活性,其中化合物(反-7,7a)-5-氨基-7-(2-氯苯基)-1,3-二氧-2,3,7,7a-四氢-1 H-吡咯[1,2-c]咪唑-6-腈、(反-7,7a)-5-氨基-7-(2-溴苯基)-1,3-二氧-2,3,7,7a-四氢-1 H-吡咯[1,2-c]咪唑-6-腈、(反-7,7a)-5-氨基-7-(2-氯-6-氟苯基)-1,3-二氧-2,3,7,7a-四氢-1 H-吡咯[1,2-c]咪唑-6-腈、(反-7,7a)-5-氨基-7-(2,6-二氯苯基)-1,3-二氧-2,3,7,7a-四氢-1 H-吡咯[1,2-c]咪唑-6-腈对禾谷镰刀菌表现出较优的活性。Using hydantoin,aldehydes and malononitrile as raw materials,pyrano[2,3-c]pyrazole derivatives was synthesized in one pot with zinc catalyst.Then,17 pyrano[2,3-c]pyrazole derivatives were obtained by different substituted aldehydes.The yield ranged from 40%to 94%.The results showed that the optimal reaction conditions are water as solvent,temperature of 80℃and 10%zinc as the catalyst.The target products were confirmed by infrared spectroscopy(IR),nuclear magnetic resonance spectroscopy(NMR)and high resolution mass spectrometry data(HRMS).The method has the advantages of mild reaction conditions,non-toxic solvent,the simple work up procedure,high yield and reused catalyst.The mycelial growth method was used to test the antifungal activity against Fusarium graminearum,Fusarium moniliforme,Fusarium oxysporum,Phytophthora parasitica var nicotianae and Rhizoctonia solani Kuhn.The bioactivity results showed that the target compounds had certain antifungal activities.Particularly,compound(trans-7,7a)-5-amino-7-(2-chlorophenyl)-1,3-dioxo-2,3,7,7a-tetrahydro-1 H-pyrrolo[1,2-c]imidazole-6-carbonitrile,(trans-7,7a)-5-amino-7-(2-bromophenyl)-1,3-dioxo-2,3,7,7a-tetrahydro-1 H-pyrrolo[1,2-c]imidazole-6-carbonitrile,(trans-7,7a)-5-amino-7-(2-chloro-6-fluorophenyl)-1,3-dioxo-2,3,7,7a-tetrahydro-1 H pyrrolo[1,2-c]imidazole-6-carbonitrile,(trans-7,7a)-5-amino-7-(2,6-dichlorophenyl)-1,3-dioxo-2,3,7,7a-tetrahydro-1 H pyrrolo[1,2-c]imidazole-6-carbonitrile displayed better activity against F.graminearum.

关 键 词：水相反应 锌-脯氨酸复合物 一锅法 氮杂吡咯西里啶类化合物 抗菌活性 

分 类 号：O626.32[理学—有机化学]