Propargylation of Ugi Amide Dianion: An Entry into Pyrrolidinone and Benzoindolizidine Alkaloid Analogues

Propargylation of Ugi adducts under the addition of excess sodium hydride in DMSO leads to direct formation of pyrrolidinone enamides, which are useful precursors of iminium intermediates and may be trapped by various nucleophiles. This approach has been applied to the formation of benzoindolizidine...

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Published inOrganic letters Vol. 20; no. 9; pp. 2568 - 2571
Main Authors Zidan, Alaa, Cordier, Marie, El-Naggar, Abeer M, Abd El-Sattar, Nour E. A, Hassan, Mohamed Ali, Ali, Ali Khalil, El Kaïm, Laurent
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.05.2018
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Organic chemistry
Physical Sciences
Science & Technology
ALIPHATIC AMIDES
MULTICOMPONENT REACTIONS
HYDROAMIDATION
PEPTIDOMIMETICS
ANNULATION
EFFICIENT SYNTHESIS
CHEMISTRY
LACTAM SYNTHESIS
HYDROAMINATION
ENAMIDES
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Summary:Propargylation of Ugi adducts under the addition of excess sodium hydride in DMSO leads to direct formation of pyrrolidinone enamides, which are useful precursors of iminium intermediates and may be trapped by various nucleophiles. This approach has been applied to the formation of benzoindolizidine alkaloids with high diversity via a Ugi/propargylation/Pictet–Spengler cyclization.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00687