| Diphenylparabanic Acid as a Versatile Synthon for the Synthesis of alpha-Diketones and alpha-Ketocarboxylic Acids. | |
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MedLine Citation:
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PMID: 22136154 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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Nobuko Watanabe; Mitsutaka Hamano; Shota Todaka; Takahiro Asaeda; Hisako K Ijuin; Masakatsu Matsumoto |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-12-2 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2011 Dec |
Date Detail:
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Created Date: 2011-12-5 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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