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8. Synthesis of Tricyclic Isoindolones via Nickel‐Catalyzed Decyclization–Addition–Cyclization of α‐Hydroxy Ynamides.

Author

Okamoto, Noriko, Yanada, Reiko, and Sueda, Takuya

Subjects
*RING formation (Chemistry), *YNAMIDES, *REGIOSELECTIVITY (Chemistry), *KETENIMINES, *ISOMERIZATION
Abstract

Regioselective addition of 1,3‐dicarbonyl compounds to N‐alkynyl‐3‐hydroxyisoindolin‐1‐ones (α‐hydroxy ynamides) was accomplished with the use of NiII salt catalysts. The reaction proceeded by a tandem decyclization–addition–cyclization mechanism, in which a ketenimine intermediate is formed via NiII‐catalyzed isomerization of α‐hydroxy ynamides. The BF3‐catalyzed intramolecular dehydrative condensation of the resulting α‐hydroxy enamides afforded tricyclic isoindolones in good yields. α‐Regioselective addition of 1,3‐dicarbonyl compounds to N‐alkynyl‐3‐hydroxyisoindolin‐1‐ones (α‐hydroxy ynamides) was accomplished with the use of NiII salt catalysts. This addition proceeded via a keteneimine intermediate, and the adducts were converted into tricyclic isoindolones. [ABSTRACT FROM AUTHOR]

Published
2019
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19. Copper-Catalyzed Tandem Amide N-Arylation and Regioselective Cyclization of 2-Alkynylbenzamides.

Author

Minami, Hideki, Sueda, Takuya, Okamoto, Noriko, Miwa, Yoshihisa, Ishikura, Minoru, and Yanada, Reiko

Subjects
AMIDE derivatives, ARYLATION, COPPER catalysts, BENZAMIDE, REGIOSELECTIVITY (Chemistry), RING formation (Chemistry), PYRIDINE derivatives, NUCLEOPHILIC reactions
Abstract

A new approach to form iminoisocoumarins from readily available and stable 2-alkynylbenzamides was developed by using a tandem copper-catalyzed N-arylation and regioselective 6- endo- dig cyclization in the presence of diaryliodonium salts, a copper catalyst, and 2,6-di- tert-butylpyridine. The arylation occurred at the nitrogen atom rather than the oxygen atom of the amide group, the alkynyl carbon, or the benzene ring of the benzamide. Cyclization occurred through a preferential nucleophilic attack by the oxygen rather than the nitrogen atom of the amide group to produce iminoisocoumarin derivatives in good to moderate yields. [ABSTRACT FROM AUTHOR]

Published
2016
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