Design and synthesis of unique thiazoloisoquinolinium thiolates and derivatives  

作　　者：Wasim Ahmed Zi-Hao Huang Zi-Ning Cui Ri-Yuan Tang 

机构地区：[1]Department of Applied Chemistry,College of Materials and Energy,South China Agricultural University,Guangzhou 510642,China [2]State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources,Integrative Microbiology Research Centre,Guangdong Province Key Laboratory of Microbial Signals and Disease Control,South China Agricultural University,Guangzhou 510642,China [3]Guangdong Laboratory for Lingnan Modern Agriculture,Guangzhou 510642,China

出　　处：《Chinese Chemical Letters》2021年第10期3211-3214,共4页中国化学快报（英文版）

基　　金：financially supported by Natural Science Foundation of Guangdong Province for Distinguished Young Scholars (Nos.2019B151502052, 2021B1515020107);the programs of National Natural Science Foundation of China (No.32072450);the International Science and Technology Cooperation Program in Guangdong (No.2020A0505100048);the Program of Science and Technology of Guangzhou (No.202002030295);the open Project of the State Key Laboratory of Crop Stress Biology for Arid Areas (No.CSBAAKF2021009)。

摘　　要：Natural isoquinolinium alkaloids possess a wide range of biological activities.The design and synthesis of mesoionic isoquinoliniums is of great importance.This paper reports the synthesis of unique mesoionic thiazoloisoquinolinium thiolates stabilized by aromatization and 1,3-dipolarization.Such compounds can be synthesized via the three component [2 + 2 + 1] cycloaddition reaction of isoquinolines with ethyl propionate and elemental sulfur in the absence of any metal catalyst and additives.Importantly,thiazoloisoquinolinium thiolates can be transformed to thioether-containing thiazoloisoquinolinium halides.A selective [4 + 2] cycloaddition can also be used to form S-bridged fused tetracyclic compounds with a thiothiamide ring unit and two quarternary carbon centres.Compound I-1 shows good bioactivity against the chlorophyll of duckweed(Lemna minor) with inhibition rate of 51.5 mg/mL.

关 键 词：ISOQUINOLINE HETEROCYCLE Zewitterionic Elemental sulfur CYCLOADDITION 

分 类 号：TQ25[化学工程—有机化工]