Tandem oxidative radical brominative addition of activated alkynes and spirocyclization: switchable synthesis of 3-bromocoumarins and 3-bromo spiro-[4,5] trienone

A K2S2O8-mediated tandem radical brominative addition of alkynoates, oxidative spiro-cyclization, and 1,2-migration of esters is reported for the synthesis of 3-bromocoumarins with high efficiency. The prepared 3-bromocoumarins are successfully converted into 3-alkynyl and 3-phosphite coumarins unde...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 3; no. 4; pp. 510 - 515
Main Authors Qiu, Guanyinsheng, Liu, Tong, Ding, Qiuping
Format Journal Article
LanguageEnglish
Published TAIPEI Chinese Chemical Soc 01.01.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MEDICINAL CHEMISTRY
ALKYNOATES
ORGANIC-SYNTHESIS
FACILE APPROACH
INTRAMOLECULAR IPSO-HALOCYCLIZATION
BIOLOGICAL-ACTIVITY
CARBONYL-COMPOUNDS
BOND FORMATION
CYCLIZATION
COUMARIN DERIVATIVES
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Summary:A K2S2O8-mediated tandem radical brominative addition of alkynoates, oxidative spiro-cyclization, and 1,2-migration of esters is reported for the synthesis of 3-bromocoumarins with high efficiency. The prepared 3-bromocoumarins are successfully converted into 3-alkynyl and 3-phosphite coumarins under mild conditions. The synthesis of a specific bromo-incorporated spiro-[4,5]trienyl-2,8-dione is achieved under the same conditions when N-methyl-N,3-diphenylpropiolate is used as the substrate.
ISSN:2052-4129
DOI:10.1039/c6qo00041j