Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

Manna, Srimanta; Jana, Sandipan; Saboo, Tapish; Maji, Arun; Maiti, Debabrata

doi:10.1039/c3cc41576g

Cited by 136 publications

(72 citation statements)

References 30 publications

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“…Melting points and NMR data of the synthesized β-nitrostyrenes were consistent with the literature values (Gairaud and Lappin, 1953; Somasekhara et al, 1971; Bose et al, 1992; Wang and Wang, 2002; Al-Zereini et al, 2007; Yan et al, 2008; Kumar et al, 2012; Manna et al, 2013; Cornell et al, 2014). …”

Section: Resultssupporting

confidence: 88%

“…1-nitro-3-((E)-2-nitrovinyl)benzene (10) (Manna et al, 2013): IR (cm −1 ): 3003, 2875, 1694, 1521, 1057, 854; 1 H NMR (CDCl 3 , 400 MHz): δ 7.51 (t, J = 8.0 Hz, 1H), 7.69-7.71 (m, 1H), 7.72 (d, J = 12.0 Hz, 1H), 8.07–8.10 (m, 1H), 8.18 (d, J = 12.0 Hz), 8.28 (s, 1H); ESI-MS (m/z): 195 (M + +1); Anal. Calcd for (C 8 H 6 N 2 O 4 ): C, 49.49; H, 3.12; N, 14.43.…”

Section: Methodsmentioning

confidence: 99%

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β-Nitrostyrenes as Potential Anti-leishmanial Agents

et al. 2016

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Development of new therapeutic approach to treat leishmaniasis has become a priority. In the present study, the antileishmanial effect of β-nitrostyrenes was investigated against in vitro promastigotes and amastigotes. A series of β-nitrostyrenes have been synthesized by using Henry reaction and were evaluated for their antimicrobial activities by broth microdilution assay and in vitro antileishmanial activities against Leishmania donovani promastigotes by following standard guidelines. The most active compounds were futher evaluated for their in vitro antileishmanial activities against intracellular amastigotes. Among the tested β-nitrostyrenes, compounds 7, 8, 9, 12, and 17 exhibited potential activities (MICs range, 0.25–8 μg/mL) against clinically significant human pathogenic fungi. However, the microbactericidal concentrations (MBCs) and the microfungicidal concentrations (MFCs) were found to be either similar or only two-fold greater than the MICs. Anti-leishmanial results demonstrated that compounds 9, 12, 14, and 18 were found to be most active among the tested samples and exhibited 50% inhibitory concentration (IC50) by 23.40 ± 0.71, 37.83 ± 3.74, 40.50 ± 1.47, 55.66 ± 2.84 nM against L. donovani promastigotes and 30.5 ± 3.42, 21.46 ± 0.96, 26.43 ± 2.71, and 61.63 ± 8.02 nM respectively against intracellular L. donovani promastigotes amastigotes respectively which are comparable with standard AmB (19.60 ± 1.71 nM against promastigotes and 27.83 ± 3.26 nM against amastigotes). Compounds 9, 12, 14, and 18 were found to have potent in vitro leishmanicidal activity against L. donovani and found to be non-toxic against mammalian macrophages even at a concentration of 25 μM. Nitric oxide (NO) estimation studies reveals that these compounds are moderately inducing NO levels.

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Section: Resultssupporting

confidence: 88%

Section: Methodsmentioning

confidence: 99%

β-Nitrostyrenes as Potential Anti-leishmanial Agents

et al. 2016

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“…For example, Maiti has shown that in the presence of stoichiometric amount of TEMPO, the reaction of tert-butyl nitrite with olefins can give rise to nitroalkenes. [15] Okamoto and Tanimoto have shown that using a Co complex as the catalyst, and BH 4 -as the hydrogen donor, the reaction of ethyl nitrite with styrenes can produce oximes as the exclusive product. [16] In 1998, Sugamoto was able to effect the same transformation using Et 3 SiH as the hydride donor employing Co Ⅱ (tpp) as the catalyst.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of α-Nitro Ketoximes from Styrenes and tert-Butyl Nitrite

Cao

Liu

Lin

et al. 2015

Synthetic Communications

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“…41 The reaction of a broad substrate scope of α,β-unsaturated carboxylic acids bearing aromatic and heterocyclic moieties smoothly proceeded under mild conditions and produced exclusively E-nitro compounds. 41 The reaction of a broad substrate scope of α,β-unsaturated carboxylic acids bearing aromatic and heterocyclic moieties smoothly proceeded under mild conditions and produced exclusively E-nitro compounds.…”

Section: Scheme 16mentioning

confidence: 99%

Recent advances in the synthesis of nitroolefin compounds

2014

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Development of methodology for the preparation of nitroolefins is of significant interest to organic chemists. Recently, numerous useful methods have been developed, mainly including direct nitration of olefinic C-H bonds, nitro-decarboxylation of aromatic α,β-unsaturated carboxylic acids, ipso-nitration of vinylboronic acids and multidehydrogenative cross-coupling reaction of (hetero)arenes with nitroethane. This review will focus on recent achievements in nitroolefin synthesis and the mechanisms of the reactions are also discussed.

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Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

Cited by 136 publications

References 30 publications

β-Nitrostyrenes as Potential Anti-leishmanial Agents

β-Nitrostyrenes as Potential Anti-leishmanial Agents

Synthesis of α-Nitro Ketoximes from Styrenes and tert-Butyl Nitrite

Recent advances in the synthesis of nitroolefin compounds

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