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  • 09월 10일 16시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제124회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Silica-gel supported One-pot Synthesis of 2-Amido benzo[b]thiophenes

2019년 9월 3일 16시 13분 26초
ORGN.P-448 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 18일 (금요일) 11:00~12:30
Organic Chemistry
저자 및
Solbin Kim, Hyun Suk Yeom1,*
Chemistry, Hanyang University, Korea
1Center for Eco-Friendly New Materials, Korea Research Institute of Chemical Technology, Korea

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.