Chinese Journal of Organic Chemistry >
Facile Synthesis of 2-(Pyridin-3-yl)-2-benzoyloxy Acetamides via Passerini Reaction and Evaluation of Their Biological Activity
Received date: 2018-01-11
Revised date: 2018-02-13
Online published: 2018-03-16
Supported by
Project supported by the Natural Science Foundation of Shandong Province (No. ZR2014BM030).
Twenty-two novel substituted 2-(pyridin-3-yl)-2-benzoyloxy acetamides were synthesized via Passerini three-component reaction involving 3-pyridinecarboxaldehyde, substituted benzoic acid, and tert-butyl isocyanide (or 1,1,3,3-tetramethylbutyl isocyanide) in water, and characterized by IR, 1H NMR, 13C NMR and HRMS. This method provides some advantages such as mild conditions, short reaction time, facile operation and high yield. Moreover, the target compounds were evaluated for their in vitro antifungal activities against two plant pathogens by the mycelium growth rate method, and the results indicated that at the dosage of 100 μg/mL, eight compounds showed moderate activities against B. cinerea with inhibition rates of 83%~89%, and seventeen compounds exhibited strong activities against S. sclerotiorum with inhibition rates of 90%~100%.
Key words： pyridine; carboxylic acid; isocyanide; synthesis design; biological activity
Zhang Junhui , Niu Lizhi , Li Ying , Liu Si , Jiang Lin . Facile Synthesis of 2-(Pyridin-3-yl)-2-benzoyloxy Acetamides via Passerini Reaction and Evaluation of Their Biological Activity[J]. Chinese Journal of Organic Chemistry, 2018 , 38(7) : 1842 -1848 . DOI: 10.6023/cjoc201801019
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