Functionalized 1-anilinoazetidin-2-ones by photochemical ring contraction of pyrazolidinones

Eǧe, Seyhan N.; Butler, William M.; BERGERS, A.; BIESMAN, B. S.; BOERMA, J. E.; CORONDAN, V. I.; Locke, K.; Meshinchi, Sussan; Ponas, Stephen H.; Spitzer, Timothy D.

doi:10.1039/p19830001111

Cited by 12 publications

(1 citation statement)

References 3 publications

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“…(4) A is slightly longer than the corresponding C--N length of 1.362(3)/~ found in 2-phenylpyrazolidin-3-one by Ege et al (1983) and longer still than that of 1.348 (2)A found in 1-phenylpyrazolidin-3-one (Sbit, Dupont, Dideberg, Liegeois & Delarge, 1987). In contrast, the C(3)--O bond distance of 1.210 (3)A is shorter than the C(3)--O bond lengths of 1.223 (3) and 1.228 (2),~ presented in the aforementioned compounds, respectively.…”

Section: Introductionmentioning

confidence: 99%

1-Benzyl-3-pyrazolidone hydrochloride

Yang¹,

Ning²,

Xu³

et al. 1994

Acta Crystallogr C

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Section: Introductionmentioning

confidence: 99%

1-Benzyl-3-pyrazolidone hydrochloride

Yang¹,

Ning²,

Xu³

et al. 1994

Acta Crystallogr C

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Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

2002

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Reductive amination is an important tool for synthetic organic chemists in the construction of carbon‐nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an aldehyde or ketone with an amine in the presence of a reducing agent. A wide variety of substrates can be used including aliphatic and aromatic aldehydes and ketones, and even benzophenones. A range of amines from ammonia to aromatic amines, including those with electron‐withdrawing substituents, can be employed. For particularly sluggish reactions, such as those involving weakly electrophilic carbonyl groups, poorly nucleophilic amines, or sterically congested reactive centers, additives such as molecular sieves or Lewis acids are often useful. This chapter focuses on those conditions in which the carbonyl component, amine, and reducing reagent react in the same vessel. This review is restricted to reductive aminations using borohydride and borane reducing agents. This chapter concentrates on reductive amination chemistry mediated by borohydride and other boron‐containing reducing agents from 1971, the year when sodium cyanoborohydride was introduced, through the middle of 1999. In addition to reductive aminations of aldehyde and ketone substrates, reactions of related structures including acetals, aminals, ketals, carboxylic acids, nitriles, and dicarbonyls that form a nitrogen‐containing ring are reviewed. Intramolecular processes in which the substrate contains both the carbonyl and amine moieties are described. The intramolecular variant is a useful method for preparing cyclic amines. All of the various boron‐containing hydride sources in reductive aminations, including labeled metal hydrides, are reviewed. Instances of reductive aminations that failed are described. Applications of this method to a solid support in parallel synthesis in combinatorial chemistry as well as reductive aminations that proceed in tandem with a second reaction such as reductive lactamizations are discussed.

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A Semi‐empirical Theoretical Study of the Structure of Pyrazolidinones and Related Compounds

Elguero

Paz

1991

Bulletin des Soc Chimique

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INDO and AM1 calculatlons with complete optimization of the geometrv have been performed on seven pyrazolldinones (neutral, cations and zwitterions) and the corresponding pyrazolinones. The geometrles, dipole moments and energies are discussed. Both methods yield acceptable results, INDC being better for the energies and A111 for the geometrles.Pyrazolidinones are a rather neglected family of heterocyclic compounds although they inclucie one of the most studied heterocycles, phenidone (l-phenylpyrazolidin-3-one), and a new class of antibiotics where the pyrazolidinone ring replaces the B-lactam.' In particular, no theoretical studies have been carried out, with the exception of a CND0/2 and a MIND0/3 calculation of the molecular and electronic structure of azomethinimine 7a. * We report here the use of IND03 and AM1 semi-empirical methods4 for the study of 3-hydroxypyrazoline l a , pyrazolidin-3-one 2a, pyrazolidin-4-one 3a, both possible salts of pyrazolidin-3-one 4a and 5a, the betaine 6a, and the azomethinimine 7a. For comparative purposes, the corresponding unsaturated compounds (b series) have also been calculated. These much more conmon derivatives, pyraz~linones,~ will not be discussed in detail, only their dipole moments and energies will be reported.

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Functionalized 1-anilinoazetidin-2-ones by photochemical ring contraction of pyrazolidinones

Cited by 12 publications

References 3 publications

1-Benzyl-3-pyrazolidone hydrochloride

1-Benzyl-3-pyrazolidone hydrochloride

Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

A Semi‐empirical Theoretical Study of the Structure of Pyrazolidinones and Related Compounds

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