Iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to form β-aminoketones and Benzo[h]quinolones

Miao, Changqing; Jiang, Liya; Ren, Lanhui; Xue, Qingxia; Fang, Yan; Shi, Weiwei; Li, Xinjian; Sheng, Jian‐Zhong; Kai, Shuangshuang

doi:10.1016/j.tet.2019.02.041

Cited by 16 publications

(9 citation statements)

References 52 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: 96%

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: 96%

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 – 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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“…It has been reported previously that 4-hydroxybutan-2-one reacts with different aromatic amines by forming β-aminoketones, which are important intermediates in the synthesis of several biologically active compounds. 24 From this…”

Section: Dalton Transactionsmentioning

confidence: 90%

Selective modification of hydroxyl groups in lignin model compounds by ruthenium-catalyzed transfer hydrogenation

2022

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Iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to form β-aminoketones and Benzo[h]quinolones

Cited by 16 publications

References 52 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

Selective modification of hydroxyl groups in lignin model compounds by ruthenium-catalyzed transfer hydrogenation

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