[目的]N-吡啶基对氯扁桃酰胺类化合物及其衍生物具有良好的抗菌活性,部分化合物还可用于治疗青光眼、干眼等疾病。旨在探索合成N-吡啶基对氯扁桃酰胺类化合物的有效途径。[方法]以对氯扁桃酸为原料,经乙酐保护羟基,羧基氯化、与氨基吡啶缩合,再经脱保护制得N-吡啶基对氯扁桃酰胺类化合物5a~5f,考察了各种氨基吡啶的反应活性和中间体4a~4f的脱保护条件。最后,通过菌丝生长速率法测试化合物5a~5f对番茄灰霉病菌的抑制率。[结果]产品总收率达76%~84%,结构经1H NMR、IR谱确证。化合物5a~5f对番茄灰霉病菌的抑制率为17%~63%。[结论]各种氨基吡啶都能与对氯扁桃酰氯有效缩合,化合物4a~4e都能在氢氧化钠/乙醇体系下脱保护,对碱较敏感的4f需在碳酸氢钠/乙醇体系下脱保护。该路线条件温和、收率高,为N-吡啶基对氯扁桃酰胺类化合物的合成提供了一种有效方法。活性测试表明化合物5a~5f具有一定的抗菌活性。 [Objective] N-pyridyl has good antibacterial activity on chloro-almond amides and their derivatives. Some compounds are also useful in the treatment of diseases such as glaucoma and dry eye. Aims To explore an effective way to synthesize N-pyridyl-chloro-mandelic acid amides. [Method] With chloro-mandelic acid as raw material, the hydroxyl groups were protected by acetic anhydride, then the carboxyl groups were chlorinated, condensed with aminopyridines, and then deprotected to produce N-pyridyl p-chloromandelamides 5a ~ 5f. Aminopyridine and the deprotection conditions of intermediates 4a-4f. Finally, the inhibitory rates of compounds 5a ~ 5f on Botrytis cinerea were tested by mycelial growth rate method. [Result] The total yield of the product reached 76% ~ 84%. The structure was confirmed by 1H NMR and IR. The inhibitory rates of compounds 5a ~ 5f against Botrytis cinerea were 17% ~ 63%. [Conclusion] All kinds of aminopyridines could be effectively condensed with chloromandelic acid chloride. All compounds 4a ~ 4e could be deprotected in sodium hydroxide / ethanol system. 4f, which is more sensitive to alkali, need to be removed under sodium bicarbonate / ethanol system protection. The route has mild conditions and high yield, which provides an effective method for the synthesis of N-pyridyl-chloro-mandelic acid amides. The activity tests showed that the compounds 5a ~ 5f had certain antibacterial activity.