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Molecules, Volume 9, Issue 1 (January-February 2004), Pages 1-38

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Research

Open AccessArticle Hexachloroacetone as a Precursor for a Tetrachloro-substituted Oxyallyl Intermediate: [4+3] Cycloaddition to Cyclic 1,3-Dienes
Molecules 2004, 9(1), 1-10; doi:10.3390/90100001
Received: 27 December 2003 / Revised: 11 January 2004 / Accepted: 12 January 2004 / Published: 31 January 2004
Cited by 7 | PDF Full-text (194 KB) | HTML Full-text | XML Full-text
Abstract
The enol phosphate 2,2-dichloro-1-(trichloromethyl)ethenyl diethyl phosphate (1), easily available by a Perkow reaction between hexachloroacetone and triethyl phosphite, reacts with sodium trifluoroethoxide/trifluoroethanol in the presence of cyclic 5-membered 1,3-dienes to furnish α,α,α',α'-tetrachloro-substituted[3.2.1]bicyclic ketones 2. A [4+3] cycloaddition of a tetrachloro-oxyallyl intermediate is [...] Read more.
The enol phosphate 2,2-dichloro-1-(trichloromethyl)ethenyl diethyl phosphate (1), easily available by a Perkow reaction between hexachloroacetone and triethyl phosphite, reacts with sodium trifluoroethoxide/trifluoroethanol in the presence of cyclic 5-membered 1,3-dienes to furnish α,α,α',α'-tetrachloro-substituted[3.2.1]bicyclic ketones 2. A [4+3] cycloaddition of a tetrachloro-oxyallyl intermediate is postulated. Full article
Open AccessArticle Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid
Molecules 2004, 9(1), 11-21; doi:10.3390/90100011
Received: 20 October 2003 / Revised: 14 January 2004 / Accepted: 15 January 2004 / Published: 31 January 2004
Cited by 9 | PDF Full-text (189 KB) | HTML Full-text | XML Full-text
Abstract
4-Heteroarylidene-2-phenyl-1,3-oxazol-5(4H)-ones were prepared by reactions of hippuric acid with substituted furan-2-carboxaldehydes or furo[b]pyrrole type aldehydes. The reactivity of various furan-2-carboxaldehyde derivatives in this reaction is discussed. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results [...] Read more.
4-Heteroarylidene-2-phenyl-1,3-oxazol-5(4H)-ones were prepared by reactions of hippuric acid with substituted furan-2-carboxaldehydes or furo[b]pyrrole type aldehydes. The reactivity of various furan-2-carboxaldehyde derivatives in this reaction is discussed. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results show that microwave irradiation shortens the reaction times while affording comparable yields. Elementary analysis, UV, IR and 1D NMR proved the structure of new synthesised compounds. 2D NMR spectroscopic measurements confirmed that the configuration at the carbon-carbon double bond corresponds to the pure E isomers of the products. Full article
Open AccessArticle Addition of Organochromium Reagents to Heteroaryl Aldehydes. Synthesis of Heteroaryl Substituted bis-Allyl Ethers and Homoallyl Ethers
Molecules 2004, 9(1), 22-28; doi:10.3390/90100022
Received: 25 September 2003 / Revised: 9 January 2004 / Accepted: 19 January 2004 / Published: 31 January 2004
PDF Full-text (165 KB) | HTML Full-text | XML Full-text
Abstract
Heteroaryl substituted allyl and homoallyl alcohols were synthesised with two different method. Synthesis of bis-allyl ethers and homoallyl ethers were carried out via reaction of allyl bromide with allyl alcohols and homoallyl alcohols, respectively. [2.3]-Wittig Rearrangement reactions of heteroaryl substituted bis-allyl ethers [...] Read more.
Heteroaryl substituted allyl and homoallyl alcohols were synthesised with two different method. Synthesis of bis-allyl ethers and homoallyl ethers were carried out via reaction of allyl bromide with allyl alcohols and homoallyl alcohols, respectively. [2.3]-Wittig Rearrangement reactions of heteroaryl substituted bis-allyl ethers were investigated using GC/MS techniques. In these reactions two unexpected products were isolated in high yield. Full article
Open AccessArticle Synthesis and Antimicrobial Activity of Some New Sugar-Based Monocyclic β-Lactams
Molecules 2004, 9(1), 29-38; doi:10.3390/90100029
Received: 14 June 2003 / Revised: 22 August 2003 / Accepted: 7 September 2003 / Published: 31 January 2004
Cited by 29 | PDF Full-text (191 KB) | HTML Full-text | XML Full-text
Abstract
The syntheses of some new sugar-based monocyclic β-lactams possessing several other functionalities in addition to the carbohydrate moiety are described. The key step was the Staudinger [2+2] cycloaddition of chiral carbohydrate Schiff base 5 with phthalimidoacetyl chloride to yield the sugar-based monocyclic [...] Read more.
The syntheses of some new sugar-based monocyclic β-lactams possessing several other functionalities in addition to the carbohydrate moiety are described. The key step was the Staudinger [2+2] cycloaddition of chiral carbohydrate Schiff base 5 with phthalimidoacetyl chloride to yield the sugar-based monocyclic β-lactam 6 as a single isomer. Treatment of protected β-lactams 6 and 8 with methylhydrazine afforded the free amino β-lactams 9 and 10. Acylation of these free amino β-lactams with benzoyl, phenoxyacetyl, cinnamoyl and phenylacetyl chloride in the presence of pyridine afforded β-lactams 11a-d and 12a-d. Some of these novel β-lactams were found to be active against Staphilococcus citrus, Klebsiella pneumoniae, Escherichia coli and Bacillus subtilis. Full article

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