Silica-gel supported One-pot Synthesis of 2-Amidobenzo[b]thiophene and Evaluation of pesticidal activity
- Title
- Silica-gel supported One-pot Synthesis of 2-Amidobenzo[b]thiophene and Evaluation of pesticidal activity
- Other Titles
- 실리카젤 기반 원-포트 2-아미도벤조티오펜의 합성 및 농약 활성 평가
- Author
- Sol Bin KIM
- Alternative Author(s)
- 김솔빈
- Advisor(s)
- 신승훈
- Issue Date
- 2019. 8
- Publisher
- 한양대학교
- Degree
- Master
- Abstract
- Benzo[b]thiophenes are widely applied scaffolds in pharmaceutical and materials sciences. Thus, the synthesis of benzo[b]thiophenes has attracted great attention over the past few decades; a number of synthetic routes for 2-substituted or 2,3-disubstituted benzo[b]thiophenes through intra- and intermolecular reactions have been reported. However, in case of synthesis of 2-amido benzo[b]thiophenes, few cases using halogen reagents (I2, NBS, and NCS) and transition-metal catalysts (Au and Rh) have been disclosed so far.
Recently, Toyota group reported the silica-gel assisted synthesis of 2-bromo benzo[b]thiophenes from the corresponding 2-(bromoethynyl)adamantylsulfide. Based on the preliminary results, we have tried the synthesis of 2-amido benzo[b]thiophenes from (o-thioanisole) substituted ynamides and desired products were obtained in high yields. Under careful optimization, one-pot reaction of ynamide coupling and cyclization reaction could be achieved by use of silica-gel as the promoter. This practical one-pot reaction affords an eco-friendly and economical synthetic route to 2-amido benzo[b]thiophenes with high yields in mild condition. This method is not relying on expensive transition-metal catalysts, no poisonous halogenated reagent, no additional purification of ynamide intermediates, and no extraction procedure of reaction mixture, which shows a power of this chemistry.
The synthesized library compounds were applied to several bioassays to evaluate the agrochemical potential as herbicides, insecticides, nematicides, and fungicides.
- URI
- https://repository.hanyang.ac.kr/handle/20.500.11754/109288http://hanyang.dcollection.net/common/orgView/200000435866
- Appears in Collections:
- GRADUATE SCHOOL[S](대학원) > THEATER & FILM(연극영화학과) > Theses (Master)
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