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A tandem Mannich addition-palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones.

ABSTRACT: A facile route towards highly functionalized 3(2H)-furanones via a sequential Mannich addition-palladium catalyzed ring closing has been elaborated. The reaction of 4-chloroacetoacetate esters with imines derived from aliphatic and aromatic aldehydes under palladium catalysis afforded 4-substituted furanones in good to excellent yields. 4-Hydrazino-3(2H)-furanones could also be synthesized from diazo esters in excellent yields by utilising the developed strategy. We could also efficiently transform the substituted furanones to aza-prostaglandin analogues.

SUBMITTER: John J 

PROVIDER: S-EPMC4077403 | biostudies-other | 2014

REPOSITORIES: biostudies-other

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A tandem Mannich addition-palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones.

John Jubi J   Târcoveanu Eliza E   Jones Peter G PG   Hopf Henning H  

Beilstein journal of organic chemistry 20140627

A facile route towards highly functionalized 3(2H)-furanones via a sequential Mannich addition-palladium catalyzed ring closing has been elaborated. The reaction of 4-chloroacetoacetate esters with imines derived from aliphatic and aromatic aldehydes under palladium catalysis afforded 4-substituted furanones in good to excellent yields. 4-Hydrazino-3(2H)-furanones could also be synthesized from diazo esters in excellent yields by utilising the developed strategy. We could also efficiently transf  ...[more]