Microwave-Assisted Approach to Nitroaniline/Aminopyridine and Its Inhibition Activity of Seed Germination

Abstract

An efficient approach to nitroaniline/aminopyridine was developed under microwave irradiation. The sulphamide and halogenated nitrobenzene/pyridine were used as starting materials. With low consumption, environment friendly, gram-scale synthesis, good substrate scope and excellent product yields, this methodology is superior to the existing approach. Additionally, these compounds 3a-3s could inhibit soybean seed germination at the concentration of 50 µM. Especially, the inhibition rate of compound 3m was higher than 90%.Nitroaniline/aminopyridine is popular in pesticide and pharmaceutical active molecules, such as fluridamine (fungicide), 1 bufluride (herbicide), 2 nitroaniline analogues (PMs, the molecule could enhance plant drought resistance) and the vinecola tablet (BCL2 inhibitor, treatment of lymphocytic leukemia) and CHIR98014 (GSK3 inhibitor, oral hypoglycemic drug). [3][4][5] In addition, nitroaniline/aminopyridine is important intermediate and industrial chemical, which are widely used in the synthesis of (aza)benzimidazole derivatives, 6 such as the flubenzimidazole (broad-spectrum anthelmintic agent), 7 omeprazole (proton pump inhibitor), 8 tetoprazole (higher activity than omeprazole), 9 thimazole (dilation of blood vessels). 10