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DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone.

ABSTRACT: The carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone with carbon dioxide promoted by the organic base 1,8-diazabicycloundec-7-ene (DBU) is reported. This reaction provides convenient access to the biologically important compounds 4-hydroxy-2H-chromen-2-one and 4-hydroxy-2(1H)-quinolinone in moderate to good yields using carbon dioxide as the carboxylation reagent. An acyl migration from nitrogen to carbon is observed in the reaction of o-acetamidoacetophenone.

SUBMITTER: Zhang WZ

PROVIDER: S-EPMC4464362 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone.

Zhang Wen-Zhen WZ Liu Si S Lu Xiao-Bing XB

Beilstein journal of organic chemistry 20150529

The carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone with carbon dioxide promoted by the organic base 1,8-diazabicycloundec-7-ene (DBU) is reported. This reaction provides convenient access to the biologically important compounds 4-hydroxy-2H-chromen-2-one and 4-hydroxy-2(1H)-quinolinone in moderate to good yields using carbon dioxide as the carboxylation reagent. An acyl migration from nitrogen to carbon is observed in the reaction of o-acetamidoacetophenone. ...[more]

PMID: 26124893

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