The synthesis and structure-activity relationship (SAR) studies of the effect of different polysubstitution patterns in the aromatic ring of 5-(acetamidomethyl)oxazolidinone antibacterials (I) on antibacterial activity are presented. Compounds I were prepared by the six-step synthesis described previously (Gregory, W. A.; et al. J. Med. Chem. [formula: see text] 1989, 32, 1673), electrophilic aromatic substitution reactions of 3-substituted compounds, and functional-group interchange reactions of 3,4-disubstituted compounds. Antibacterial evaluation of compounds I against Staphylococcus aureus and Enterococcus faecalis gave the following results. The 2,4- and 2,5-disubstituted derivatives have weak or no antibacterial activity. Antibacterial activities of 3,4-disubstituted compounds are comparable to those of the 4-monosubstituted analogues for small 3-substituents (smaller than Br), but decline rapidly for larger 3-substituents. 3,4-Annulated derivatives are comparable in activity to their open-chain analogues. 3,5-Disubstituted and 3,4,5- and 2,4,6-trisubstituted derivatives are devoid of antibacterial activity.

METALATION OF OLEFINS AND DiENES IN ALFIN POLYMERIZATION 3786potassium dodecanoate indicate that the transition occurs with the CS alcohol, but additional evidence, now being obtained, will be necessary before more definite ideas as to the extent of penetration of these long chain alcohols into the soap micelle can be advanced. SummaryAdditional evidence as to the presence of two loci of solubilization in soap micelles is obtained from solubilization data of hydrocarbon and polar compounds in soap solutions containing added electrolyte. The addition of potassium chloride to a 0.32 N potassium tetradecanoate (KCLO solution results in an enhancement of solubility of n-heptane and a decrease of n-octanol. With 0.05 N KC14-KC1 solutions, the solubilities of both polar and non-polar compounds increase. However, after the initial increase up to about 0.50 N potassium chloride, the solubility of the alcohol again decreases. Even though the critical micelle concentration of a soap depends only on the equivalent concentration of the ion opposite in charge to that of the colloidal electrolyte, the nature of both anion and cation affect solubilization. Thus in the solubilization of n-heptane for equivalent concentrations of additive, KC1 > K&OI > K4Fe(CN)6.3HpO whereas the reverse order holds when n-octanol is solubilized. However, these latter data present additional proof as to the two loci of solubilization, one in the bydrocarbon center of the micelle, the other in tbe palisade layer in the region occupied by the soap molecules. As the chain length of the solubilized alcohol is increased, there is a gradual transition from polar type to non-polar type solubilization most strikingly indicated when comparing Ca and CIO alcohols. Qualitative measurements of viscosity indicate that the addition of very small amounts of long chain alcohols to soap-salt systems result in the formation of very viscous, almost gel-like, systems. The maximum viscosities always QCCW a t concentrations of alcohol below the limit of solubilization (as indicated by turbidity).ST. PAUL, MINK.

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The reaction of molecular cyanogen azide with hydrocarbon olefins at 0-35°g ives 1-alkylalkylidenecyanamides and/or 1-cyanoaziridines in high yields. Evidence is presented favoring a 1,3-dipolar concerted addition of the azide followed by opening of the resulting triazoline to a diazonium zwitterion and loss of nitrogen from this labile species to yield products. Linear and simple cyclic olefins generally produce alkylidenecyanamides as the major product, often to the exclusion of A-cyanoaziridines. With selected cyclic olefins this reaction is an effective means of forming either ring-enlarged or ring-contracted product. Ring-enlargement products and aziridines are also formed by reacting cyclic alkylidenecyanamides with diazomethane. The 1-alkylalkylidenecyanamides are readily hydrolyzed to ketones; the cyanogen azide reaction thus permits facile, low-temperature conversion of olefins to ketones. More highly substituted olefins often produce W-cyanoaziridines, and these compounds are obtained in high yield from polycyclic olefins such as norbornene and dicyclopentadiene. The W-cyanoaziridine produced from norbornene, 3-cyano-3-azatricyclo[4.2.1.02•4]octane, is cleaved with LiAlH, to the parent aziridine, which is readily converted to 7-aminonorbornane (by hydrolysis and dehalogenation) and sj/w-7-aminonorbornene (by hydrolysis and dehydro chlorination).Since we reported the synthesis of cyanogen azide (N3CN) in 1964,1 two broad areas of chemical reactivity for this highly reactive compound have been defined. We disclosed at that time the facile addition of the molecular azide to olefins accompanied by nitrogen loss (1) F. D. Marsh and . E.

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