Reaction of β-aminopropionohydroxamic acid with aldehydes and ketones

Luk’yanov, O. A.; Gordeev, P. B.

doi:10.1007/bf02495976

Cited by 3 publications

(2 citation statements)

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“…This finding is in agreement with the reactions of β-AlaHA with aliphatic aldehydes or ketones solely giving products 3. 4 In this work, we report that the condensation of glycine HA (GlyHA 4) with acetone proceeds similarly 3 to afford cyclic HA 5 (Scheme 1).…”

mentioning

confidence: 86%

3-Hydroxy-2,2-dimethylimidazolidin-4-one: the regioselective synthesis and chiral crystallization

Vystorop

Kostyanovsky

2002

Mendeleev Communications

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confidence: 86%

3-Hydroxy-2,2-dimethylimidazolidin-4-one: the regioselective synthesis and chiral crystallization

Vystorop

Kostyanovsky

2002

Mendeleev Communications

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“…9 The 1 H and 13 C NMR spectra of compounds 3 and 4 (in CD 3 OD or DMSO d 6 ) show no signals of azome thine forms, which rules out the ring chain tautomer ism slow on the NMR time scale. 11 The tautomerism be tween the hydroxy amide and hydroxy nitrone forms (O=C-N-OH HO-C=N→O) of acids 3 and 4 fast on the NMR time scale is not observed as well. This is evident from a comparison of the chemical shifts of the carbonyl carbon atoms in the 13 C NMR spectra of com pounds 3 (DMSO d 6 , δ C , 171.2) and 4 (CD 3 OD, δ C , 174.4) and the corresponding model compounds existing in fixed tautomeric forms, viz.…”

Section: Methodsmentioning

confidence: 90%

Cyclic hydroxamic acids derived from α-amino acids 1. Regioselective synthesis, structure, NO-donor and antimetastatic activities of spirobicyclic hydroxamic acids derived from glycine and DL-alanine

et al. 2010

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The reactions of glycine hydroxamic and DL alanine hydroxamic acids with triacetonamine are chemoselective and afford 1 hydroxy 7,7,9,9 tetramethyl 1,4,8 triazaspiro[4.5]decan 2 one (3) and (±) 1 hydroxy 3,7,7,9,9 pentamethyl 1,4,8 triazaspiro[4.5]decan 2 one (4), re spectively. The X ray diffraction study showed that compound 3 crystallizes as a solvate with MeCN (1 : 1). As shown by ESR measurements, spiro hydroxamic acids 3 and 4 are NO donors in in vitro biological systems. The NO donor activity of compounds 3 and 4 was found to be substantially higher in the presence of DMSO. Homologue 4 is a stronger NO donor than 3. Compound 4 also exhibits high antimetastatic activity (81%) on the B16 melanoma model.

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ChemInform Abstract: Reaction of β‐Aminopropionohydroxamic Acid with Aldehydes and Ketones.

Luk’yanov¹,

Gordeev²

1998

ChemInform

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Reaction of β-Aminopropionohydroxamic Acid with Aldehydes and Ketones.-Condensation of β-aminopropionohydroxamic acid (I) with aliphatic ketones or aldehydes affords the 1-N-hydroxy-2alkyltetrahydropyrimidin-6-ones (III). Similarly, tautomeric mixtures of pyrimidinones (V) and Schiff bases (VI) in ratios depending on the substitution pattern and on the NMR solvent used are obtained from (I) and aromatic aldehydes. -(LUK'YANOV, O. A.; GORDEEV, P. B.; Izv.

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Reaction of β-aminopropionohydroxamic acid with aldehydes and ketones

Cited by 3 publications

References 1 publication

3-Hydroxy-2,2-dimethylimidazolidin-4-one: the regioselective synthesis and chiral crystallization

3-Hydroxy-2,2-dimethylimidazolidin-4-one: the regioselective synthesis and chiral crystallization

Cyclic hydroxamic acids derived from α-amino acids 1. Regioselective synthesis, structure, NO-donor and antimetastatic activities of spirobicyclic hydroxamic acids derived from glycine and DL-alanine

ChemInform Abstract: Reaction of β‐Aminopropionohydroxamic Acid with Aldehydes and Ketones.

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