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Tartakovsky, V. A.; Ioffe, Sema L.; Dilman, Alexander D.; Tishkov, Alexander A.

doi:10.1023/a:1015056024675

Cited by 14 publications

(6 citation statements)

References 10 publications

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“…In the dinitro compound was obtained by Robert Clauser, as the formula C 3 H 5 AC 6 H(OH)(NO 2 ) 2 AOCH 2 COOH shown, two nitro groups were both bound with the benzene ring, whereas in the recently obtained dinitro compound, one nitro group is attached to the side chain. Also, this compound particularly exists in quinone-aci form, which is considered as a reactive and unstable intermediate in the thermal decomposition of explosives [8,9]. The versatility of nitro compounds in organic synthesis is largely owing to their easy availability and transformation into a variety of diverse functionalities [10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Isolation, structure, and properties of quinone-aci tautomer of a phenol-nitro compound related to eugenoxyacetic acid

Định¹,

Huan²,

Toan³

et al. 2010

Journal of Molecular Structure

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Section: Introductionmentioning

confidence: 99%

Isolation, structure, and properties of quinone-aci tautomer of a phenol-nitro compound related to eugenoxyacetic acid

Định¹,

Huan²,

Toan³

et al. 2010

Journal of Molecular Structure

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“…± N,N-Bis(silyloxy)enamines (BENA) can be used as very convenient reagents for the functionalization of the C(b) atom in readily available aliphatic nitro compounds by both electrophilic and nucleophilic reagents [2]. Introduction.…”

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confidence: 99%

Chemistry of N,N-Bis(silyloxy)enamines, Part 5

Lesiv

Ioffe

Strelenko

et al. 2002

HCA

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Dedicated to Professor Dieter Seebach on the occasion of his 65th birthday Aliphatic nitro compounds can be considered as good precursors of a wide variety of a-azolyl-substituted oximes. The double silylation of convenient aliphatic nitro compounds and the subsequent N,C-coupling of the resulting N,N-bis(silyloxy)enamines 3 with N-silylated azoles 4 lead to the formation of the silylated a-azolylsubstituted oximes 6, which can be smoothly desilylated to give the target a-azolyl-substituted oximes 5. The mechanism of the key step of this process ± N,C-coupling ± includes the generation of corresponding conjugated nitrosoalkenes 7 (Schemes 4 and 5). The contribution of the chain mechanism in the overall process is considered as well. The studies of the scope and limitations of this reaction, as well as the optimization of its conditions were accomplished. The configuration of the CN bond in oximes was established by NMR.

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“…Silyl nitronates are versatile reagents [1,2] in organic synthesis, for example,f or nitro-aldol reactions, [3] nitro-Michael reactions [4] and alkene-cycloadditions leading to isoxazolines. [5] Asymmetric nitro-aldol reactions using silyl nitronatesh ave been achieved.…”

Section: Introductionmentioning

confidence: 99%

Metal‐Catalyzed Synthesis of Functionalized 1,2,4‐Oxadiazoles from Silyl Nitronates and Nitriles

Nikodemiak

Koert

2017

Adv Synth Catal

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Them etal-catalyzed cycloaddition of silyl nitronates and nitriles leading to 1,2,4-oxadiazolesi s described. Silver(I) triflate (AgOTf) and and ytterbium(III) triflate [Yb(OTf) 3 ]a re suitable catalysts.A variety of functional groups is tolerated in the nitrile. Ther eactionw orks wellf or alkenyla nd aryl silyl nitronatesw hile the use of alkyl silyl nitronates is less efficient. Mechanistic studies are in favour of an elimination of tert-butyl(dimethyl)silanol (TBSOH) after the cycloaddition step.T he new approachh as also been applied for the synthesis of the drug ataluren.

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Cited by 14 publications

References 10 publications

Isolation, structure, and properties of quinone-aci tautomer of a phenol-nitro compound related to eugenoxyacetic acid

Isolation, structure, and properties of quinone-aci tautomer of a phenol-nitro compound related to eugenoxyacetic acid

Chemistry of N,N-Bis(silyloxy)enamines, Part 5

Metal‐Catalyzed Synthesis of Functionalized 1,2,4‐Oxadiazoles from Silyl Nitronates and Nitriles

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