Iodine-Mediated Oxidative Rearrangement of α,β-Unsaturated Diaryl Ketones: A Facile Access to 1,2-Diaryl Diketones

Bansode, Ajay H.; Suryavanshi, Gurunath

doi:10.1021/acsomega.9b00833

Cited by 24 publications

(20 citation statements)

References 71 publications

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“…The reaction did not proceed in toluene or acetonitrile (Entries 1 and 2), but dimethyl sulfoxide (DMSO) was effective for the aromatization and nitrophenol 5a was obtained in 26% yield (Entry 3). [20][21][22] This reaction proceeded efficiently to afford 5a in 61% yield even when the amount of iodine was decreased to 10 mol%. However further decreasing the iodine amount to 5 mol% was not effective for the conversion (Entries 4 and 5).…”

Section: Resultsmentioning

confidence: 95%

One-Pot and Metal-Free Synthesis of 3-Arylated 4-Nitrophenols via Polyfunctionalized Cyclohexanones from β-Nitrostyrenes

Asahara¹,

Hiraishi²,

Nishiwaki³

2020

Preprint

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β-Nitrostyrenes underwent the Diels-Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated 5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated 4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one-pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group such as a thienyl group could be introduced into the nitrophenol framework.

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Section: Resultsmentioning

confidence: 95%

One-Pot and Metal-Free Synthesis of 3-Arylated 4-Nitrophenols via Polyfunctionalized Cyclohexanones from β-Nitrostyrenes

Asahara¹,

Hiraishi²,

Nishiwaki³

2020

Preprint

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“…The aromatization of 4a using iodine was then attempted ( Table 2). The reaction did not proceed in toluene or acetonitrile ( Table 2, entries 1 and 2), but dimethyl sulfoxide (DMSO) was effective for the aromatization, and nitrophenol 5a was obtained in 26% yield ( Table 2, entry 3) [21][22][23]. This reaction proceeded efficiently to afford 5a in 61% yield even when the amount of iodine was decreased to 10 mol %.…”

Section: Resultsmentioning

confidence: 99%

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

Asahara

Hiraishi

Nishiwaki

2020

Beilstein J. Org. Chem.

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β-Nitrostyrenes underwent a Diels–Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated-5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated-4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group, e.g., a thienyl group could be introduced into the nitrophenol framework.

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“…3‐(4‐Fluorophenyl)‐1‐(4‐methylphenyl)‐2‐propen‐1‐one (2e) . Colorless solid (2.11 g, 8.8 mmol, 88 %).…”

Section: Methodsmentioning

confidence: 99%

Three Step Synthesis of Fully and Differently Arylated Pyridines

et al. 2020

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Condensation of -(2-pyridyl)enamine and α, -unsaturated ketone in the presence of FeCl 3 under air afforded highly substituted pyridines. In this transformation, FeCl 3 acted as not only an acid catalyst but also an oxidant for the intermediate dihydropyridine. The substituents could be easily modi- [a] 466 fied by altering the substrates to obtain tri-and tetraarylpyridines including bipyridines and terpyridine. Synthesis of differently substituted pentaarylpyridines was consequently achieved via only three steps from commercially available reagents with simple experimental manipulations.[a] 2 equiv. of enamine 1B were used.

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Iodine-Mediated Oxidative Rearrangement of α,β-Unsaturated Diaryl Ketones: A Facile Access to 1,2-Diaryl Diketones

Cited by 24 publications

References 71 publications

One-Pot and Metal-Free Synthesis of 3-Arylated 4-Nitrophenols via Polyfunctionalized Cyclohexanones from β-Nitrostyrenes

One-Pot and Metal-Free Synthesis of 3-Arylated 4-Nitrophenols via Polyfunctionalized Cyclohexanones from β-Nitrostyrenes

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

Three Step Synthesis of Fully and Differently Arylated Pyridines

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