1965
DOI: 10.1021/jo01015a056
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The Formation of N,N'-Dihydroxyethylenebisamides from Glyoxal and Selected Amides

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Cited by 22 publications
(6 citation statements)
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“…In general, the base-catalyzed reactiono f glyoxal with amides affords 1,2-bisacylamino-1,2-ethanediols. [11] Similar reactions, conducted in the late 1960s, between glyoxal and formamide or sulfonamide derivatives gave rise to tetrahydroxypiperazines together with the corresponding N,N'-disub-stituted1 ,2-diamino-1,2-ethanediols (Scheme 1). [12] However, this protocol was not generale nougha nd somea mides failed to give the expecteda dducts.…”
Section: Introductionmentioning
confidence: 94%
See 1 more Smart Citation
“…In general, the base-catalyzed reactiono f glyoxal with amides affords 1,2-bisacylamino-1,2-ethanediols. [11] Similar reactions, conducted in the late 1960s, between glyoxal and formamide or sulfonamide derivatives gave rise to tetrahydroxypiperazines together with the corresponding N,N'-disub-stituted1 ,2-diamino-1,2-ethanediols (Scheme 1). [12] However, this protocol was not generale nougha nd somea mides failed to give the expecteda dducts.…”
Section: Introductionmentioning
confidence: 94%
“…Certainly, the direct condensations of cyanamide with electrophiles have long been known, although the resulting reaction mixtures are often too complex for conclusive analysis. In general, the base‐catalyzed reaction of glyoxal with amides affords 1,2‐bisacylamino‐1,2‐ethanediols . Similar reactions, conducted in the late 1960s, between glyoxal and formamide or sulfonamide derivatives gave rise to tetrahydroxypiperazines together with the corresponding N , N ′‐disubstituted 1,2‐diamino‐1,2‐ethanediols (Scheme ) .…”
Section: Introductionmentioning
confidence: 99%
“…An article by Vail etal. stressed the importance of keeping the reaction slightly basic and the reaction temperature low in the reaction of amides with glyoxal to give N , N ′‐dihydroxylethylenebisamides [8]. The reaction of 1 with glyoxal at 45°C under these conditions produced a clear solution that, when examined by 13 C NMR, clearly contained a single product.…”
Section: Resultsmentioning
confidence: 99%
“…Effect of Basic Media oil A-Methylolimides.-Methylolated imides exhibited a tendency to hydrolyze which paralleled the parent imides. A-Methylolsuccinimide was stable at pH 7-9 for at least 2 hr, whereas methylolated maleimide and phthalimide (heated to effect solution) hydrolyzed relatively rapidly; generally the pH decreased from an 8-10 range to below pH 7 in less than the time required to obtain an nmr spectrum (about 5…”
Section: Experimental Section15mentioning
confidence: 99%