Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 1, Pages 683-692Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02310
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Funding
- National Natural Science Foundation of China [21871087]
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Highly atom-economical tandem reactions have been developed for the synthesis of pyrano[3,2-b]indoles or cyclopenta[b]indoles tethered with 7-, 8-, or 9-membered rings. These reactions involve a carbon-carbon sigma-bond cleavage reaction of cyclic beta-ketoesters followed by intramolecular O-H/C-H coupling to give pyrano[3,2-b]indoles or C3 nucleophilic addition to afford cyclopenta[b]indoles.
Highly atom-economical tandem reactions have been developed for the synthesis of pyrano[3,2-b]indoles or cyclopenta[b]indoles tethered with 7-, 8-, or 9-membered rings. These reactions first undergo a carbon-carbon sigma-bond cleavage reaction of cyclic beta-ketoesters. Next, in the presence of CuCl2 and Ag2CO3, intramolecular O-H/C-H coupling occurs to give pyrano[3,2-b]indoles. This is the first example for capture of the enoloxyl radical of the intramolecular C-O bond formation reaction, whereas C3 nucleophilic addition afforded cyclopenta[b]indoles using TsOH center dot H2O.
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