1981
DOI: 10.1002/hlca.19810640220
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The Reaction of Pyruvic Acid with Amines and Aminoesters Reexamined. Preliminary communication

Abstract: SummaryPhenylglycine esters react with pyruvic acid to give u-met hylsuccinic amides 9 instead of the expected Schiff bases 8, analogously to p-anisidine but unlike aniline.Aza-allylic carbanions (1) are considered important intermediates in organic synthesis2), their generation however suffers from the general disadvantage that the bases used are rather sophisticated (alkali amides, organolithiums, alkali silylamides), difficult to handle in large scale preparations. Access to anions 1 might be possible using… Show more

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Cited by 8 publications
(2 citation statements)
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“…The synthesis of N ‐substituted 9‐aminofluorenes, by virtue of their inimitable importance in biological materials and medicine, represents a great challenge to organic chemists. One of the most general strategies for their formation is the addition of organometallic reagents onto N ‐substituted 9‐fluoreneimines 8. Recently, the direct N ‐functionization of the sp 3 CH bond has emerged to provide an appealing approach for the synthesis of valuable nitrogen‐containing compounds 7a,9.…”
Section: Methodsmentioning
confidence: 99%
“…The synthesis of N ‐substituted 9‐aminofluorenes, by virtue of their inimitable importance in biological materials and medicine, represents a great challenge to organic chemists. One of the most general strategies for their formation is the addition of organometallic reagents onto N ‐substituted 9‐fluoreneimines 8. Recently, the direct N ‐functionization of the sp 3 CH bond has emerged to provide an appealing approach for the synthesis of valuable nitrogen‐containing compounds 7a,9.…”
Section: Methodsmentioning
confidence: 99%
“…The following supporting information can be downloaded at: https: //www.mdpi.com/article/10.3390/molecules27134047/s1, Materials and Characterization, Tables S1 to S3, Figures S1 to S5, and NMR Data of the Products [27,[43][44][45][46][47][48][49][50][51], Figures S6-S18.…”
Section: Supplementary Materialsmentioning
confidence: 99%