New synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles

Lin, Yang‐I; Lang, Stanley A.; Lovell, Maurice F.; PERKINSON, N. A.

doi:10.1021/jo01337a031

Cited by 78 publications

(41 citation statements)

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“…The bromine atom of the CH 2 Br group lies out of the plane of the phenyl ring, and the two O -CH 3 bonds lie close to the plane of the phenyl ring and are oriented parallel to each other in a syn,syn conformation ͓the designations syn and anti refer to the orientations of the C͑3͒O-CH 3 and C͑5͒O-CH 3 bonds relative to the orientation of the C͑4͒-H bond͔. With regard to this feature, other molecules containing 3,5-dimethoxyphenyl rings ͑with hydrogen atoms in the 2-, 4-, and 6-positions͒ display a range of different conformations, including other examples with syn,syn conformations ͑Lin et al ., 1979;Bartholomew et al, 2000͒, examples of syn,anti conformations ͑Lynch et al, 1994Peters et al, 1993;Pettit et al, 1988͒, an example with two independent molecules in the asymmetric unit with anti,anti and syn,anti conformations ͑Yin et al, 2002͒, and an example with two independent 3,5-dimethoxyphenyl moieties in a given molecule that adopt syn,syn and syn,anti conformations ͑Yin and Zhang, 2002͒.…”

Section: Discussion a Crystal Structure Of 35-dmbbmentioning

confidence: 99%

Structural properties of methoxy derivatives of benzyl bromide, determined from powder X-ray diffraction data

et al. 2005

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Structure determination of 3,5-dimethoxybenzyl bromide and 3,4,5-trimethoxybenzyl bromide has been carried out from laboratory powder X-ray diffraction data using the direct-space Genetic Algorithm technique for structure solution followed by Rietveld refinement. These two compounds are of interest for their potential use as building blocks for the synthesis of dendritic materials. Although the two molecules differ only in the presence/absence of the methoxy group at the 4-position of the aromatic ring, the structural properties of the two materials are significantly different. © 2005 International Centre for Diffraction Data.

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Section: Discussion a Crystal Structure Of 35-dmbbmentioning

confidence: 99%

Structural properties of methoxy derivatives of benzyl bromide, determined from powder X-ray diffraction data

et al. 2005

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“…In contrast, the cyclization reaction using hydroxylamine instead of HOSA gave the desired products (3m-1, 2) in more than 78% yield. 12) Thus, the obtained pyridine derivatives (3m-1, 2) were reacted with methyl iodide to give the corresponding pyridinium salts (4m-1, 2). A low-field chemical shift of the pyridine ring protons in 1 H NMR spectra certainly suggested the formation of pyridinium salts (4m-1, 2).…”

Section: General Proceduresmentioning

confidence: 99%

Synthesis and insecticidal activity of 1,2,4-oxadiazole and 1,2,4-thiadiazole derivatives

et al. 2011

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A series of 5-substituted 1,2,4-oxadiazoles and 1,2,4-thiadiazoles were prepared as muscarinic acetylcholine receptor agonists and evaluated for their insecticidal activity. These derivatives were synthesized through sequential reactions consisting of the condensation of pyridinecarboamides or pyridinecarbothioamides with N,N-dimethylacetamide dimethyl acetal, cyclization with hydroxylamine, quaternization by alkyl halide and reaction with sodium borohydride. All 1,2,4-oxadiazoles and 1,2,4-thiadiazoles synthesized were evaluated for insecticidal activity and their structure-activity relationships are discussed. It was discovered that many compounds were active against representative insects such as Nilaparvata lugens, Nephotettix cincticeps and Aphis craccivora. In particular, it was also found that 3-pyridyl-substituted derivatives of 1,2,4-oxadiazole and 1,2,4-thiadiazole exhibited good insecticidal activity against all the insects tested. Among the compounds evaluated, 3-methyl-5-(1,2,5,6-tetrahydropyridin-3-yl)-1,2,4-thiadiazole (9m-2) showed the highest activity against Nilaparvata lugens, and provided a high level of activity against the imidacloprid-resistant strain. Based on the preliminary binding assay using the binding inhibition of mAChR antagonist [ 3 H]NMS to the nerve-cord membranes as an index of the binding activity, 9m-2 exhibited a range of potencies for the insect muscarinic receptor.

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“…The reaction mixture was then cooled (ice bath), stirred at 0 °C (1 h) and extracted with CH 2 Cl 2 . The combined organic extracts were washed with water and dried (MgSO 4 ) (12). The N-hydroxyamidine 10 (0.6 g, 2.5 mmol) was dissolved in acetic acid (5.0 mL) and heated at 120 °C (2 h).…”

Section: 3-dihydro-2-ethylbenzo[b]furan-2-carboxylic Acid Dimethylamentioning

confidence: 99%

Preparation of analogues of efaroxan and KU14R as potential imidazoline receptor subtype 3 ligands

Farn¹,

Ramsden²,

Morgan³

2008

Journal of Heterocyclic Chem

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The preparation and characterization of new analogues of the imidazoline insulin secretagogue efaroxan 1 are described. These include 1,2,4-triazole, 1,3,4-oxadiazole, pyrimidine, 1,4,5,6-tetrahydropyrimidine and 1,2-dihydro-1,2,4,5-tetrazine analogues. Bromination of 2,3-dihydro-2-ethylbenzo[b]furan-2-carbonitrile 19 gives the 3,3-dibromo analogue 28, which is readily hydrolysed to the corresponding ketone 29. Reduction of this ketone gives the alcohol 31 as a mixture of diastereoisomers that is converted to the fluoride 32 using diethylaminosulfur trifluoride.

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New synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles

Cited by 78 publications

References 0 publications

Structural properties of methoxy derivatives of benzyl bromide, determined from powder X-ray diffraction data

Structural properties of methoxy derivatives of benzyl bromide, determined from powder X-ray diffraction data

Synthesis and insecticidal activity of 1,2,4-oxadiazole and 1,2,4-thiadiazole derivatives

Preparation of analogues of efaroxan and KU14R as potential imidazoline receptor subtype 3 ligands

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