A one-pot, two-step protocol for the synthesis of libraries of remarkable functionalized sulfone analogues of 9b,10,10a,10b-tetrahydro-1-cyclopropa[][1,4]thiazino[4,3-]quinolines is described. A class of various functionalized molecular skeletons was obtained by cyclopropanation of quinolinium zwitterionic thiolates. The reaction pathway involves the formation of a [2 + 1] cycloaddition intermediate followed by a [5 + 1] cycloaddition.
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http://dx.doi.org/10.1021/acs.joc.1c02175 | DOI Listing |
J Org Chem
June 2024
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou 510641, P. R. China.
Here, reported is a new method for divergent synthesis of functionalized tetrahydroquinolines (THQs), featuring a biomedically interesting azabicyclo[4.1.0]heptane core, proceeding with mild conditions, good substrate and functionality tolerance, and operational simplicity.
View Article and Find Full Text PDFJ Org Chem
November 2021
Affiliated Hospital of Integrated Traditional Chinese and Western Medicine, Nanjing University of Chinese Medicine, Nanjing 210028, Jiangsu, China.
A one-pot, two-step protocol for the synthesis of libraries of remarkable functionalized sulfone analogues of 9b,10,10a,10b-tetrahydro-1-cyclopropa[][1,4]thiazino[4,3-]quinolines is described. A class of various functionalized molecular skeletons was obtained by cyclopropanation of quinolinium zwitterionic thiolates. The reaction pathway involves the formation of a [2 + 1] cycloaddition intermediate followed by a [5 + 1] cycloaddition.
View Article and Find Full Text PDFChem Sci
February 2020
Department of Applied Chemistry , Kyung Hee University, Yongin , 17104 , Republic of Korea . Email:
A divergent cyclopropanation reaction has been accomplished the dearomative addition of sulfur ylides to activated N-heteroarenes. A series of biologically significant molecular skeletons was obtained by the direct cyclopropanation of quinolinium zwitterions. Furthermore, a straightforward synthetic route to optically enriched cyclopropane-fused heterocycles was developed using sulfur ylides as chiral nucleophiles in the 1,4-dearomative reaction.
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