Document Detail


Diphenylparabanic Acid as a Versatile Synthon for the Synthesis of alpha-Diketones and alpha-Ketocarboxylic Acids.
MedLine Citation:
PMID:  22136154     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Diphenylparabanic acid 4 was found to react with >2 eq of organolithiums at -78 degrees C to effectively give the corresponding symmetrical alpha-diketones 5. However, upon treatment with 1 eq of organolithium, 4 gave mainly 5-substituted 5-hydroxyimidazolidine-2,4-diones 7. On the other hand, Grignard reagents were less reactive toward 4 at low temperature, and selectively gave 7 even if more than 1 eq of the reagents were used. A tandem process in which 4 was first reacted with a Grignard reagent and then reacted in one-pot with an organolithium effectively gave the unsymmetrical α-diketone 6. 5-Substituted 5-hydroxyimidazolidine-2,4-diones 7 were useful as versatile precursors for preparing alpha-ketocarboxylic acids 8 as well as unsymmetrical alpha-diketones 6.
Authors:
Nobuko Watanabe; Mitsutaka Hamano; Shota Todaka; Takahiro Asaeda; Hisako K Ijuin; Masakatsu Matsumoto
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-12-2
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2011 Dec 
Date Detail:
Created Date:  2011-12-5     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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