A new synthetic approach for novel 4-substituted-5-nitroimidazoles

Perfetti, Patricia; Kaafarani, Mustapha; Vanelle, Patrice; Crozet, Maxime D.

doi:10.1016/s0040-4039(02)00767-0

Cited by 13 publications

(7 citation statements)

References 11 publications

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“…While Crozet and co‐workers24–26 reported the exclusive formation of 6 ao , when 6 a was treated with 1 and potassium hydroxide in DMSO at room temperature, we isolated a mixture of 4‐benzenesulfonylmethyl‐1‐methyl‐5‐nitroimidazole ( 6 ao , 42 %) and 15 % of the corresponding 2‐isomer ( 6 ap , Scheme ) in accordance with earlier reports 23. Only one regioisomer was obtained in the reaction of 1‐methyl‐4‐nitroimidazole ( 6 b , Scheme ) with 1 − .…”

Section: Resultsmentioning

confidence: 99%

Reactions of Nitroheteroarenes with Carbanions: Bridging Aromatic, Heteroaromatic, and Vinylic Electrophilicity

Seeliger

Błażej

Bernhardt

et al. 2008

Chemistry A European J

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The relative rate constants for the vicarious nucleophilic substitution (VNS) of the anion of chloromethyl phenyl sulfone (1-) with a variety of nitroheteroarenes, for example, nitropyridines, nitropyrroles, nitroimidazoles, 2-nitrothiophene, and 4-nitropyrazole, have been determined by competition experiments. It was shown that nitropyridines are approximately four orders of magnitude more reactive than nitrobenzene. Among the five-membered heterocycles 2-nitrothiophene is the most active followed by nitroimidazoles and 4-nitropyrazole. Nitropyrroles are the least electrophilic nitroheteroarenes with reactivities comparable to nitrobenzene. Quantum chemically calculated methyl anion affinities (B3LYP/6-311G(d,p)//B3LYP/6-31G(d)) of the nitroarenes correlated only moderately with the partial relative rate constants. The correlation of these activities with the LUMO energies of nitroarenes is even worse. By measuring the second-order rate constants of the addition of 1- to nitroarenes and to diethyl arylidenemalonates 10, it was possible to link the electrophilic reactivities of nitroheteroarenes with the comprehensive electrophilicity scale based on the linear-free-energy-relationship log k(20 degrees C)=s(N+E).

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Section: Resultsmentioning

confidence: 99%

Reactions of Nitroheteroarenes with Carbanions: Bridging Aromatic, Heteroaromatic, and Vinylic Electrophilicity

Seeliger

Błażej

Bernhardt

et al. 2008

Chemistry A European J

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“…The 4-tosylmethyl group was chosen because sulfones are well-known to be employed in many synthetic methodologies 34 and it can be used further for the preparation of various 4-substituted heterocycles. 35 Owing to the fact that the bromoheterocyclic sulfone 4 is a strongly C-H acidic sulfone, its expected solubility in the basic medium of the Suzuki-Miyaura experimental conditions offers the opportunity to develop Suzuki-Miyaura reactions in aqueous water.…”

Section: Methodsmentioning

confidence: 99%

An efficient aqueous microwave-assisted Suzuki–Miyaura cross-coupling reaction in the thiazole series

et al. 2009

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“…Conversely, the anion derived from 4-benzenesulfonylmethyl-1-methyl-5-nitro-1H-imidazole 88 is reported to react with 2, 2-dinitropropane (under entrainment conditions with 2-nitropropane anion) in an S RN 1 fashion to afford 4-substituted-5-nitroimidazole alkene 89, according to Scheme 29 [156].…”

Section: Aliphatic Substrates With Ewg At the α α α α Carbonmentioning

confidence: 99%

Strategies in Synthetic Radical Organic Chemistry. Recent Advances on Cyclization and SRN1 Reactions

Rossi¹,

Peñéñory

2006

COS

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A new synthetic approach for novel 4-substituted-5-nitroimidazoles

Cited by 13 publications

References 11 publications

Reactions of Nitroheteroarenes with Carbanions: Bridging Aromatic, Heteroaromatic, and Vinylic Electrophilicity

Reactions of Nitroheteroarenes with Carbanions: Bridging Aromatic, Heteroaromatic, and Vinylic Electrophilicity

An efficient aqueous microwave-assisted Suzuki–Miyaura cross-coupling reaction in the thiazole series

Strategies in Synthetic Radical Organic Chemistry. Recent Advances on Cyclization and SRN1 Reactions

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