Synthesis, structure and cytotoxic activity of new 1‐[5‐organylsilyl(germyl)‐2‐furyl (thienyl)]nitroethenes

Игнатович, Л.; Muravenko, V.; Romanovs, Vitalijs; Sleiksha, Ilze; Шестакова, И.; Domrachova, Ilona; Belyakov, Sergey; Popelis, J.; Lukevics, É.

doi:10.1002/aoc.1712

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Preparation Of (E)-1-(4-methylphenyl)-2nitroethene (1a)1

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2022

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“…The solid was recrystalized with a mixed solvent (hexane/ dichloromethane 10:1) to afford nitrostyrene 1a [24] (1.99 g, 12.2 mmol, 76%) as yellow needles. The other nitroalkenes 1b-f [25][26][27][28][29] were prepared in the same way.…”

Section: Preparation Of (E)-1-(4-methylphenyl)-2nitroethene (1a)mentioning

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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