Citation: Wasim Ahmed, Zi-Hao Huang, Zi-Ning Cui, Ri-Yuan Tang. Design and synthesis of unique thiazoloisoquinolinium thiolates and derivatives[J]. Chinese Chemical Letters, ;2021, 32(10): 3211-3214. doi: 10.1016/j.cclet.2021.03.065 shu

Design and synthesis of unique thiazoloisoquinolinium thiolates and derivatives

Wasim Ahmed ^a ,
Zi-Hao Huang ^a ,
Zi-Ning Cui ^{a, b, c, *,} ,
Ri-Yuan Tang ^{a, c, *,}

a.
Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China
b.
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
c.
Guangdong Laboratory for Lingnan Modern Agriculture, Guangzhou 510642, China

ziningcui@scau.edu.cn

rytang@scau.edu.cn

Received Date: 28 December 2020
Revised Date: 21 January 2021
Accepted Date: 24 March 2021
Available Online: 26 March 2021

Figures(4)

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 μg/mL.
- Isoquinoline,
- Heterocycle,
- Zewitterionic,
- Elemental sulfur,
- Cycloaddition
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