Synthesis of 4‐imidazolin‐2‐ones <i>via</i> the birch reduction of hydantoins

Divanfard, Hosein R.; Ibrahim, Yehia A.; Joullié, Madeleine M.

doi:10.1002/jhet.5570150437

Cited by 6 publications

(2 citation statements)

References 3 publications

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“…In the case of hydantoin, photochemical cleavage of the ring has also been observed. 18 Figure 2: Several modified hydantoin derivatives.…”

Section: Chemicalmentioning

confidence: 99%

“…39,40 In some cases, the reduction was also realized with the excess of lithium-liquid ammonia in tert-butyl alcohol to give compound (26). 41 Since the thiocarbonyl group is more polarized than the carbonyl group, it is expected that thiohydantoins are more easily reduced than hydantoin. This is also evident by the fact that reduction of thiohydantoin by sodium in ethanol or with Raney nickel to give 4imidazolidinones under conditions that does not affect hydantoins.…”

Section: Reductionmentioning

confidence: 99%

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Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Kumar¹

2021

Synlett

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Hydantoin and its analogs such as thiohydantoin and iminohydantoin have received substantial attention both from a chemical and biological point of view. Several compounds of this class have shown useful pharmacological activities such as anticonvulsant, antitumor, antiarrhythmic, herbicidal, and others that lead in some cases to clinical applications. Because of broad-spectrum activities, intensive research efforts have been dedicated in industry and academia to the synthesis and structural modifications of hydantoin and its derivatives. Realizing the importance of hydantoin in organic and medicinal chemistry, we also initiated a research program to successfully design and develop the new routes/methods resulting in the formation of hydantoin, thiohydantoin, and iminohydantoin substituted at different positions particularly at the N-1 position without following protection-deprotection strategy. Given the fact that the combination of two or more pharmacophoric groups may lead to hybrid molecules which result in a mixed mechanism of action on the biological target. We, therefore, further extended the developed strategy for the synthesis of new types of hydantoin-based hybrid molecules by combining hydantoin with a triazole, isoxazoline, and phosphate scaffolds as another pharmacophoric group to exploit diverse biological functions.

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“…In the case of hydantoin, photochemical cleavage of the ring has also been observed. 18 Figure 2: Several modified hydantoin derivatives.…”

Section: Chemicalmentioning

confidence: 99%

Section: Reductionmentioning

confidence: 99%

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Kumar¹

2021

Synlett

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Hydantoin and Its Derivatives

Avendaño

Menéndez

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Hydantoins are a group of closely related substances for which several general patterns regarding their physical properties, chemical reactivity, synthesis, and analysis can be found. Physical properties of hydantoin derivatives, including melting point and ionization properties, are discussed in terms of their relationship with molecular association through hydrogen bonds. A survey of their spectral properties (uv, ir, nmr, luminescence, and mass spectra) is also given. Treatment of chemical reactivity is descriptive, with little or no emphasis on mechanistic aspects. The most common synthetic and analytical methods are also briefly discussed. Medicinal applications are commented on and various other industrial applications of hydantoins are also covered.

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Birch Reduction

2010

Comprehensive Organic Name Reactions and Reagents

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The reduction of aromatic compounds by alkali metal in liquid ammonia in the presence of alcohol is generally known as the Birch reduction or metal‐ammonia reduction. The Birch reduction uses the ammonia‐solvated electrons arising from alkali metal as the reducing agent, which bears the extremely negative single‐electron redox potential. Once the solvated electron adds to aromatic system, the radical anion is quenched by alcohol, so that cyclohexa‐1,4‐diene derivatives are often produced from benzene derivatives without further reduced species. It has been pointed out that the existing alkali metal also reacts with alcohol to generate hydrogen, in a reaction known as the hydrogen reaction. It has been reported that both the rate and yield of the Birch reduction decreases in the order of Li>Na>K. One of the advantages associated with the Birch reduction is its efficient steric control on the aromatic system. The applications of the Birch reduction are to convert aryl alkyl ethers into 1‐alkoxycyclohexa‐1,4‐dienes and also to reduce acetylenes stereospecifically to trans‐olefins and to hydrogenate graphite and carbon single‐walled nanotubes (SWNTs). The Birch reaction has also been found to cleave the CC bond in the presence of the aromatic system.

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Synthesis of 4‐imidazolin‐2‐ones via the birch reduction of hydantoins

Abstract: The reduction of 5‐(5‐methyl‐2‐furyl)hydantoin to 4‐(5‐methyl‐2‐luryl)‐4‐imidazolin‐2‐one is described.

Cited by 6 publications

References 3 publications

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Hydantoin and Its Derivatives

Birch Reduction

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