1-芳基-4-乙氧羰基-5-氨基-1,2,3,-连三唑和几种亲电子试剂的反应及产物抗菌性能的研究

STUDIES ON REACTION AND ANTIBACTERIAL ACTIVITY OF 1-ARYL-4-ETHOXYCARBONYL -5-AMINO -1,2,3-TRIAZOLE WITH SEVERAL ELECTROPHILIC REAGENTS

本文研究1-芳基-4-乙氧羰基-5-氨基-1,2,3,-连三唑(1)同过量乙酸,乙酸酐、乙酰氯、苯甲酰氯以及甲酰胺等的反应,制得1的14种新衍生物:1-H-4-乙氧羰基-5-芳胺基-1,2,3-连三唑(2 b～d),1-酰基-4-乙氧羰基-5-芳胺基-1,2,3-连三唑(3a～d),1-芳基-4-乙氧羰基-5-乙酰胺基-1,2,3-连三唑-(4a～d)以及1-甲酰基-4-乙氧羰基-5-对硝基苯胺基-1,2,3-连三唑(5a),1-苯甲酰基-4-乙氧羰基-5-对硝基苯胺基-1,2,3-连三唑(5b),1-对氨苯甲酰基-4-乙氧羰基-5-对硝基苯胺基-1,2,3-连三唑(5c)。所有化合物的结构,均经元素分析及波谱分析确证,并筛选了一些化合物的抗菌作用。

Upon treatment of 1-aryl-4-ethoxycarbonyl-5-amino-1,2, 3-triazoles (1) with excess acetic acid, acetic anhydride, acetyl chloride, benzoyl chloride, formamide, etc., fourteen new derivatives of 1 were obtained in good yields, such as, 1-H-4-ethoxycarbonyl-5-arylamino-1, 2, 3-triazoles (2b～d), 1-RCO-4-ethoxycarbonyl-5-arylamino-1, 2, 3-triazoles (3a～d), 1-aryl-4-ethoxycarbonyl-5-acetylamino-1,2,3-triazoles (4a～d)and 1-formoyl-4-ethoxycarbonyl - 5 -p -nitrophenylamino- 1, 2, 3 - triazole (5a), 1- benzoyl - 4- ethoxycarbonyl - 5 - p -nitrophenylamino- 1,2,3 -triazoles (5b), 1-p-chlorobenzoyl- 4- ethoxycarbonyl -5-p-nitrophenylamino-1,2, 3-triazoles (5c). Some of them were rearrangement products. Structures of all heterocyclic compounds were identified by elemental analyses, IR, ~1HNMR and MS. Inhibiting effects of some compounds on B. substili, E. coli, E. aerogenes and S. aureus were also screened.