Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue -, Pages 906-912Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.11.102
Keywords
acyl migration; carbon dioxide; carboxylation; cyclization; condensation
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Funding
- National Natural Science Foundation of China [21172026]
- Fundamental Research Funds for the Central Universities [DUT15LAB21]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT13008]
- Ministry of Education, People's Republic of China [T2011056]
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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.
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