Syntheses and reactions of N-tosylphenacylamines with bases have been systematically examined. Monomeric C-methoxy-imines are available from some of these reactions. C-Methoxyphenacylarylamines, made by two routes, were converted into monomeric imines on treatment with noble-metal catalysts. The boron trifluoridecatalysed reactions of aryl aldehydes with sulphonamides provide a new and convenient route to N-sulphonylarylimines.

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(±)-Lineatin (1), the aggregation pheromone of an ambrosia beetle, was synthesized in five steps from anhydromevalonolactone (5) in 10% overall yield. The key step in the synthesis was a photochemical cycloaddition of 5 and allene. This photolysis produced two regioisomers (ca. 3:2) and efforts to improve the regioselectivity by varying the photolysis conditions or substituents on the allene were unsuccessful.[Formula: see text]

1-(2,4-Dichlorophenyl)-2-phenylpropen-1-one (2) is identified as a potent antibacterial agent. A compound, 2-chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan++ +-1-one (5) has been designed with the intention of its acting as a pro-drug, liberating the lethal species 2 specifically within the target anaerobic bacterial cell following bioreduction by bacterial ferredoxin or related electron transfer proteins. The synthesis and biological activity of 5 is described and compared with the activities of the analogous alpha-bromo ketone 6 and alpha-fluoro ketone 7. Synthesis of 6, 7, and the corresponding alpha-hydroxy ketone 11 is also described.

2-Chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2phenylpropan-1-one Hydrochloride, a Novel, Nonmutagenic Antibacterial with Specific Activity Against Anaerobic Bacteria.-Coupling of 2,4-dichlorobenzaldehyde (I) with the phenylethenylmagnesium bromide (II) yields the allylic alcohol (III). Oxidation of (III) with barium manganate followed by reaction of the unsaturated ketone (IV) thus obtained with the heterocycles (V) gives the Michael adducts (VI). These are lithiated and then treated with N-chlorosuccinimide or bromine to form the title product (VIIa) and the analogous halides (VIIb) or (VIII). The corresponding fluoride (XI) is prepared from (IV) via the epoxide (IX) and carbinol (X) as outlined in the reaction scheme. -(DICKENS, J. P.; ELLAMES, G. J.; HARE, N. J.; LAWSON, K. R.; MCKAY, W. R.; METTERS, A. P.; MYERS, P. L.; POPE, A. M. S.; UPTON, R. M.; J. Med. Chem. 34 (1991) 8, 2356-2360; Dep. Med.