Three-component condensations of aldehydes with N-methoxycarboxamides

Marson, Charles M.; Pucci, Sabrina

doi:10.1016/j.tetlet.2004.10.058

Cited by 11 publications

(3 citation statements)

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“…For background to hydroxamic acids in biological and coordination chemistry, see: Miller (1989); Lipczynska-Kochany (1991); Kurzak et al (1992); Whittaker et al (1999). For reactions of -amino hydroxamic acids with aldehydes and ketones resulting in 3-hydroxyimidazolidin-4-one derivatives, see: Vystorop et al (2002Vystorop et al ( , 2003; Marson & Pucci (2004). For related structures, see: Krä mer & Fritsky (2000); Ś wią tek- Kozłowska et al (2000); Krä mer et al (2002); Kovbasyuk et al (2004).…”

Section: Related Literaturementioning

confidence: 99%

“…These properties have provoked current interest in the development of novel synthetic routes for preparation of new selective hydroxamate chelating agents and siderophore mimics. Recently it was found that the reactions of α-amino hydroxamic acids with aldehydes and ketons do not result in the open-chain Schiff base hydroxamic acids but afford fivemembered cyclic products containing residues of 3-hydroxyimidazolidine-4-one (Marson & Pucci, 2004;Vystorop et al, 2002;Vystorop et al, 2003). Here we describe a crystal structure of the title structure, 2-methyl-2-(pyridine-2-yl)-3-hydroxyimidazolidine-4-one, obtained as a result of the condensation of glycine hydroxamic acid and 2-acetylpyridine.…”

Section: Data Collectionmentioning

confidence: 99%

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(2RS)-3-Hydroxy-2-methyl-2-(2-pyridyl)imidazolidine-4-one

et al. 2009

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The title structure, C9H11N3O2, is a racemate. The chiral centre is situated at the N—C—N C atom of the imidazolidine ring. The interplanar angle between the mean planes of the pyridine and imidazolidine rings is 89.41 (5)°. The methyl group is in a trans position with respect to the pyridine N atom. In the crystal, the molecules are arranged in zigzag layers parallel to the b axis. The molecules within the layers are interconnected by strong O—H⋯N and weak N—H⋯O hydrogen bonds; the former take place between OH groups and amine N atoms and the latter between the amine N atom and the carbonyl O atom. In addition, C—H⋯O interactions are also present.

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Section: Related Literaturementioning

confidence: 99%

Section: Data Collectionmentioning

confidence: 99%

(2RS)-3-Hydroxy-2-methyl-2-(2-pyridyl)imidazolidine-4-one

et al. 2009

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“…It should also be added that these authors developed a similar methodology under different acidic conditions with the use of acetals as the source of the corresponding aldehydes. 26 More appealing seems the ABB9C 4C coupling of amides, aldehydes and dienophiles (Scheme 9). Beller et al further developed this methodology, which involves the Diels-Alder reaction of a 1-acylamino-1,3-diene intermediate 19 with different dienophiles (dialkyl acetylenedicarboxylates, acrylonitrile, maleic anhydride or maleimides), to efficiently prepare highly functionalized cyclohexene and cyclohexadiene derivatives 20-23 in a diastereoselective manner.…”

Section: Enolizable Carbonyl Compoundsmentioning

confidence: 99%

Chemo-differentiating ABB′ multicomponent reactions. Privileged building blocks

2007

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Heterocycles from Hydroxylamines and Hydroxamic Acids

Katkevičs¹,

Kukosha²,

Lukevics³

2010

Patai's Chemistry of Functional Groups

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Hydroxylamines and hydroxamic acids are polyfunctional organic molecules and several reactive intermediates can be generated from them, therefore they have found broad application in the synthesis of various nitrogen and oxygen containing heterocycles by means of nulceophilic substitution or addition, electrophilic intramolecular aromatic substitution, as well as [2+4] and [3+2] cycloaddition reactions. This chapter surveys synthesis of heterocycles from the title compounds highlighting some distinguished reaction mechanism aspects, regio‐ and stereo selectivity issues and experimental details. It is arranged according to the size and type of heterocycles that allows fast but also explanatory insight into synthesis of the particular cycles.

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Three-component condensations of aldehydes with N-methoxycarboxamides

Cited by 11 publications

References 10 publications

(2RS)-3-Hydroxy-2-methyl-2-(2-pyridyl)imidazolidine-4-one

(2RS)-3-Hydroxy-2-methyl-2-(2-pyridyl)imidazolidine-4-one

Chemo-differentiating ABB′ multicomponent reactions. Privileged building blocks

Heterocycles from Hydroxylamines and Hydroxamic Acids

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