In this study,we designed a convenient method,to total synthesis of fl avonols especially for C-5 substituted ones and derivatives on a large scale.Beginning from the inexpensively available 2,4,6-trihydroxyacetopheno...In this study,we designed a convenient method,to total synthesis of fl avonols especially for C-5 substituted ones and derivatives on a large scale.Beginning from the inexpensively available 2,4,6-trihydroxyacetophenone through Aldol condensation reaction,I2/DMSO cyclization reaction,Oxone“one pot”oxidation,kaempferol(1)and derivative(2)was obtained in an overall yield of 35%.The structures of the target compound and key intermediates were verifi ed by MS,IR,1H-NMR and 13C-NMR techniques,and the structure of 5a was further confi rmed by X-ray diff raction analysis.展开更多
Main observation and conclusion The reaction of 2-alkynylanisoles/sulfides with SOCl_(2) and DMSO was conducted to conveniently furnish the biologically interesting 3-(methylthio)-benzo[b]furans/thiophenes via intramo...Main observation and conclusion The reaction of 2-alkynylanisoles/sulfides with SOCl_(2) and DMSO was conducted to conveniently furnish the biologically interesting 3-(methylthio)-benzo[b]furans/thiophenes via intramolecular cyclization.DMSO acts as a solvent as well as a sulfur source and can also be replaced with DMSO-d_(6),enabling the incorporation of the SCD3 moiety of DMSO-d_(6) to the 3-position of the heterocyclic frameworks.展开更多
基金supported by the National Natural Science Foundation of China(51472071,51272016,51072043)Startup Foundation of Hefei University of Technology,China(JZ2014HGBZ0371,JZ2014HGBZ0358)~~
基金Science and Technology Project of Gansu Province(grant No.18YF1NA128)the Natural Science Foundation of Liaoning Province(grant No.201602712).
文摘In this study,we designed a convenient method,to total synthesis of fl avonols especially for C-5 substituted ones and derivatives on a large scale.Beginning from the inexpensively available 2,4,6-trihydroxyacetophenone through Aldol condensation reaction,I2/DMSO cyclization reaction,Oxone“one pot”oxidation,kaempferol(1)and derivative(2)was obtained in an overall yield of 35%.The structures of the target compound and key intermediates were verifi ed by MS,IR,1H-NMR and 13C-NMR techniques,and the structure of 5a was further confi rmed by X-ray diff raction analysis.
基金We acknowledge the National Natural Science Foundation of China(No.21472136)for financial support.
文摘Main observation and conclusion The reaction of 2-alkynylanisoles/sulfides with SOCl_(2) and DMSO was conducted to conveniently furnish the biologically interesting 3-(methylthio)-benzo[b]furans/thiophenes via intramolecular cyclization.DMSO acts as a solvent as well as a sulfur source and can also be replaced with DMSO-d_(6),enabling the incorporation of the SCD3 moiety of DMSO-d_(6) to the 3-position of the heterocyclic frameworks.
