Cobalt-Catalyzed Carbonylative Cyclization of Pyridinyl Diazoacetates for the Synthesis of Pyridoisoquinolinones

Dicobalt octacarbonyl-catalyzed carbonylative cyclization of pyridinyl diazoacetates is developed for the synthesis of pyridoisoquinolinones under mild conditions (room temperature) in a carbon monoxide atmosphere. Moreover, a synthetic method for various pyridoisoquinolinones from ethylpyridinyl ar...

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Published inOrganic letters Vol. 18; no. 1; pp. 104 - 107
Main Authors Baek, Yonghyeon, Kim, Sunghwa, Jeon, Bongkeun, Lee, Phil Ho
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.01.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SELECTIVE CARBONYLATION
OCTACARBONYL DICOBALT
PALLADIUM
CROSS-COUPLING REACTIONS
INSERTION
CARBON-MONOXIDE
METAL CARBENE
DIAZO-COMPOUNDS
ETHYL DIAZOACETATE
N-TOSYLHYDRAZONES
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Summary:Dicobalt octacarbonyl-catalyzed carbonylative cyclization of pyridinyl diazoacetates is developed for the synthesis of pyridoisoquinolinones under mild conditions (room temperature) in a carbon monoxide atmosphere. Moreover, a synthetic method for various pyridoisoquinolinones from ethylpyridinyl aryl acetates is demonstrated through diazotization using TsN3 and DBU followed by Co-catalyzed carbonylation to generate ketene intermediates, which can subsequently undergo intramolecular cyclization under mild conditions in a carbon monoxide atmosphere in a semi-one-pot fashion.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03340