期刊
CHEMICAL SCIENCE
卷 6, 期 10, 页码 5847-5852出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc02379c
关键词
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资金
- Department of Science and Technology (DST), New Delhi, India [SR/S1/OC-48/2012]
- Indian Institute of Technology Madras (IITM)
Rhodium catalyzed synthesis of substituted tetrahydropyridines was accomplished from readily accessible thio-tethered N-sulfonyl-1,2,3-triazoles. The reaction involves tandem rhodium catalyzed 1,2-sulfur migration in beta-thio-alpha-diazoimines, generated from thio-tethered N-sulfonyl-1,2,3-triazoles, to thio-substituted 1-azadiene and subsequent self aza-Diels-Alder reaction. Interestingly, the methodology was effectively extended to the synthesis of fused tetrahydropyridines, dihydropyridines and cyclohexenes through the in situ trapping of the intermediate, 1-azadiene, with various dienophiles such as enol ether, enamine, ketene S, S-acetal, alkyne, alkene and diene. Furthermore, the direct conversion of propargyl sulfides to (fused)-tetrahydropyridines was also achieved through the successful integration of copper and rhodium catalysts in one-pot.
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