Gold-catalyzed Synthesis Of Multifunctionalized Cyclopentadiene And Its Application In Pesticide Molecule Desig

In this paper,cheap and easily available enaminones and propargylic esters were used as substrates.Under the activation of gold catalyst,propargylic esters further generated 1,2-acyloxy migration,producing highly reactive vinylcarbenes species,and further（3+2）cyclization addition reaction with functionalized unsaturated olefins to obtain highly functionalized cyclopentadienyl isobutyrate esters.43 target compounds were designed and synthesized,and after simple conversion,various related derivatives were obtained with good yields,and the relevant mechanisms were studied.With（Chenopodium amaranticolor）as the test object and Potato virus Y（PVY）as the research object,the antiviral activity of the obtained target compounds was preliminarily tested.The work of this paper is summarized as follows:1.Using enaminones compounds and propargylic esters as reaction substrates,the optimal reaction conditions were obtained by screening the template reaction conditions.43 cyclopentadienyl isobutyrate compounds were designed and synthesized,and their structures were characterized by ¹H NMR,¹³C NMR,¹⁹F NMR,and HRMS to determine the structure of the target compound 3aa-3Ba.Multiple related derivatives 4ao-7ao were obtained by further conversion of the obtained target compound.2.By using deuterium experiments,specific hydrogen atoms of the reaction substrate are labeled to obtain deuterium substrates.The target product was obtained under template reaction conditions,and the experimental results were consistent with the proposed mechanism.The key intermediate 3Ba was isolated.3.The anti-PVY activities of compounds 3aa-3Ba were preliminarily screened by the half-leaf method using Chenopodium amaranticolor plants at a concentration of500 mg/L.The experimental results showed that the therapeutic activities of compounds 3ka,3ma,3na,3oa,3ae,3af,3ah,3aj were 60.1%,58.4%,68.3%,62.6%,57.6%,63.4%,65.7%,and 66.5%,respectively.The therapeutic effect was significantly higher than that of the control drug ribavirin（45.6%）.The protective activities of compounds 3la,3ad,and 3an were 45.7%,46.2%,48.8%,and 48.2%,respectively,and the therapeutic effect was slightly higher than that of the control drug ribavirin（42.1%）.