Palladium-Catalyzed Synthesis of Isoquinolinones via Sequential Cyclization and N-O Bond Cleavage of N-Methoxy-o-alkynylbenzamides

A palladium-catalyzed controlled 6-endo-dig cyclization process has been developed for the chemoselective synthesis of isoquinolin-1-ones from N-alkoxy-o-alkynylbenzamides. The mechanism and scope of the reaction have also been investigated. Deuterium-labeling studies were used to confirm the intram...

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Bibliographic Details
Published inSynlett Vol. 24; no. 4; pp. 475 - 478
Main Authors Jithunsa, Manita, Ueda, Masafumi, Aoi, Naoki, Sugita, Shoichi, Miyoshi, Tetsuya, Miyata, Okiko
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.2013
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
regioselectivity
amides
ACID
ONE-POT SYNTHESIS
alkynes
ELIMINATION
CASCADE
cyclization
PI-OLEFIN
palladium
TRISUBSTITUTED ISOXAZOLES
STEREOSELECTIVE-SYNTHESIS
ISOCOUMARINS
PHOTOLYSIS
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Summary:A palladium-catalyzed controlled 6-endo-dig cyclization process has been developed for the chemoselective synthesis of isoquinolin-1-ones from N-alkoxy-o-alkynylbenzamides. The mechanism and scope of the reaction have also been investigated. Deuterium-labeling studies were used to confirm the intramolecular 1,5-hydrogen shift as a key step in the transformation.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0032-1318159