A new and straightforward approach to highly functionalized 2-imidazolin-2-ones

Substituted aminocarbonyldiazenecarboxylates reacted with 1,3-diketones or beta -ketoesters under mild reaction conditions in the presence of ZrCl4 to give highly functionalized imidazolin-2-ones via the corresponding Michael adducts. Reaction of unsymmetrical precursors resulted in the formation of...

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Bibliographic Details
Published inSynlett no. 8; pp. 1237 - 1240
Main Authors Bombek, S, Lenarsic, R, Kocevar, M, Polanc, S
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
regioselectivity
AZODICARBOXYLATE
ASYMMETRIC-SYNTHESIS
DIAZENES
AMINO
aminocarbonyldiazenecarboxylates
STEREOSELECTIVE AMINATION
REACTIVITY
ALPHA-HYDRAZINO ACIDS
ELECTROPHILIC AMINATION
ONE N ATOM
cyclizations
imidazolin-2-ones
amination
DERIVATIVES
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Summary:Substituted aminocarbonyldiazenecarboxylates reacted with 1,3-diketones or beta -ketoesters under mild reaction conditions in the presence of ZrCl4 to give highly functionalized imidazolin-2-ones via the corresponding Michael adducts. Reaction of unsymmetrical precursors resulted in the formation of only one regioisomer.
ISSN:0936-5214
DOI:10.1055/s-2001-16053