The reaction of N-(3-phenylpropionyloxy)phthalimide (1a) and N-tosyloxy (5a,b) derivatives with nucleophiles was examined and found to give the products via Lossen-type rearrangement. In order to obtain the scope of this reaction mechanism, further studies the reaction of several N-sulfonyloxyimide derivatives with various nucleophiles under similar conditions were carried out and found to afford the
AgF-mediated Hofmann-type reaction of N-tosyl cyclic imides with silicate esters
作者:Qian Zhang、Yunbing Liu、Shijun Deng、Hongju Zhan、Lin Zhao、Dong Li
DOI:10.1016/j.tetlet.2023.154683
日期:2023.9
A facile and efficient AgF-mediated Hofmann-type reaction of N-tosyl cyclicimides with silicate esters was developed. The N-tosyl cyclicimides undergo a Hofmann-type rearrangement/alkoxylation reaction in which the silicate ester acted as the alkoxy source. This reaction proceeds under simple and mild conditions to generate a series of anthranilic acid-derived carbamates in moderate to good yields