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p. 1364-1368
Received: 5 February 2005 / Accepted: 5 March 2005 / Published: 30 November 2005
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| Download PDF Full-text (59 KB) Abstract: Alumina or silica gel are used as catalysts for a solvent-free oxidation of benzoins to the corresponding benzils. These catalysts are easily recovered after completion of the reactions, which are carried out either by heating in a sand bath or using microwave irradiation. Comparison of the results obtained with both catalysts indicates that all the reactants examined were oxidized faster on alumina than on silica under these conditions.
p. 1369-1376
Received: 20 January 2005; in revised form: 24 January 2005 / Accepted: 14 March 2005 / Published: 30 November 2005
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| Download PDF Full-text (64 KB) Abstract: R,R’-disubstituted sulfoximines were phosphorylated with O,O–diethylchlorophosphate and phosphorothionate to obtain new organophosphorus compounds. Afterpurification they were characterized by GC-MS and 1 H-NMR. The toxicity of thesynthesized O,O-diethyl N-(R,R’-disubstituted sulfoximine) phosphoro-amidothionateswas assayed on Musca domestica. It was found that the methyl phenyl derivative was themost toxic compound, followed by the dipropyl and dibutyl derivatives. The dihexylcompound was the less toxic of all the assayed compounds, being one hundred times lesstoxic than a paraoxon standard The anticholinesterasic activity of the correspondingphosphoramidates was assayed on homogenates of house flies’ heads, giving valuessimilar to paraoxon for the methyl phenyl derivative.
p. 1377-1386
Received: 7 June 2005; in revised form: 25 October 2005 / Accepted: 26 November 2005 / Published: 30 November 2005
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| Download PDF Full-text (143 KB) Abstract: A series of 22 novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5- carboxamidine derivatives were synthesized and evaluated for in vitro antibacterial activity against S. aureus and methicillin resistant S. aureus (MRSA), E. coli, E. faecalis and for antifungal activity against C. albicans. Compound 59 [1-(2,4-dichlorobenzyl)-N- (2-diethylaminoethyl)-1H-benzimidazole-5-carboxamidine], with a 3,4-dichlorophenyl group at the C-2 position, displayed the greatest activity (MIC = 3.12 μg/mL against both some bacteria and the fungus C. albicans).
p. 1387-1398
Received: 28 June 2005; in revised form: 5 September 2005 / Accepted: 10 September 2005 / Published: 30 November 2005
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| Download PDF Full-text (96 KB) Abstract: The sulfamide functional group is increasingly relevant in both medicinal and bioorganic chemistry. We report here practical access to a series of N2,N5-substituted five-membered cyclosulfamides. The five-membered heterocyclic motif was prepared starting from proteogenic amino acids and chlorosulfonyl isocyanate via the Mitsunobu reaction. Selected chemical and spectral proprieties and the antimicrobial evaluation of these compounds are detailed.
p. 1399-1408
Received: 4 August 2005; in revised form: 11 October 2005 / Accepted: 15 October 2005 / Published: 30 November 2005
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| Download PDF Full-text (93 KB) Abstract: Preparation of bisbenzofuran-2-yl-methanone (1), the corresponding ketoxime 4, semicarbazone and thiosemicarbazone 3a and 3b, ether derivatives of the ketoximes 5a-j and the alcohol 2 are described. These substances have been prepared in excellent yields. All the synthesized compounds except 5i have been tested against five different microorganisms and some of them were found to be active against some of the species studied.
p. 1409-1412
Received: 16 August 2005; in revised form: 19 August 2005 / Accepted: 23 August 2005 / Published: 30 November 2005
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| Download PDF Full-text (119 KB) Abstract: A facile, high yielding synthesis of 9,10-dihydro-9,10-ethano- anthracene-11- carboxylic acid methyl ester using a modified commercial domestic microwave oven is reported.
p. 1413-1418
Received: 25 August 2005; in revised form: 22 September 2005 / Accepted: 23 September 2005 / Published: 30 November 2005
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| Download PDF Full-text (54 KB) Abstract: A simple and efficient method for the preparation of 1-methyl-3-oxo-7- oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester (1) is described. The first step is a highly regioselective Diels-Alder reaction between 2-methylfuran and methyl-3-bromo- propiolate. A remarkably difficult ketal hydrolysis reaction was effected by treatment with HCl, a simple reagent that was shown to be more efficient, in this case, than commonly used more elaborate methods.
p. 1419-1428
Received: 24 March 2005; in revised form: 26 July 2005 / Accepted: 26 July 2005 / Published: 30 November 2005
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| Download PDF Full-text (97 KB) Abstract: The oxidation of 2-(3,4-dihydronaphthalen-1-yl)-ethanol (1) with a variety ofthallium(III) salts was investigated. An indan, formed by a ring contraction reaction, wasobtained in good to moderate yields under a variety of reaction conditions: i) thalliumtriacetate (TTA) in aqueous AcOH; ii) thallium tris-trifluoroacetate (TTFA) in aqueousTFA; iii) TTFA in CH2 Cl2 ; iv) thallium tripropionate (TTP) in aqueous propionic acidand v) thallium tris-[(S)-(-)-triacetoxypropionate] in aqueous (S)-(-)-2-acetoxypropionicacid. On the other hand, the reaction of compound 1 with TTA in methanol led to a 2:1mixture of the corresponding cis- and trans-dimethoxylated compounds, respectively.These compounds were formed by a thallium-promoted addition of methanol to thedouble bond.
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