synthetic route to 1-hydroxyimidazoles. By selection of the starting materials substituents can be readily introduced into the 2,4 and/or 5 positions of the imidazole ring which is formed via the intermediacy of a gem-aminoalcohol. The reactions of the N-hydroxyl function are discussed.In a study of cellulosic fiber-polymer interactions4,5) we have been concerned with the synthesis of imidazoles6-9) and other polyaza heterocycles suitable for the attachment of vinylic moieties having differing reactivity ratios.10) Thus, although 4(5)-vinylimidazole has been described,11-15) the procedure is not amenable to facile variation and this alkene does not readily copolymerize with a wide range of monomens.13) Our attention was thus directed to the fact that almost exactly half a century ago Diels discovered16) that when aldehydes (RCHO) and butane-2,3-dione monoxime (I) are shaken with aqueous ammonia, a clan of compounds is formed by the elimination of two moles of water. Their reductive conversion into trisubstituted imidazoles (III) and their reversible hydrolysis to products considered to be the diols (IV) led16) to their formulation as II.Although the synthesis of the somewhat labile oxaziridine ring system has been achieved17,18) by several, usually oxidative, procedures, its generally limited stability in alkaline solutions and its apparent ease of formation in this alkaline condensation suggested that a re-examination of this group of products was merited.Repetition of the prescribed procedure smoothly afforded II in good yield. Examination of this compound then disclosed (for R=Ph) that IV is a simple hydrate of II and that the transformations

No abstract

The condensation products of rhodanine and some of its derivatives with benzaldehyde sulphonic acids have been prepared with a view to obtaining compounds of increased fungicidal properties. The products differ from the majority of previously prepared rhodanine-aldehyde condensation products in that they are appreciably soluble in water. From a fungitoxicological standpoint this increased solubility may well increase the activity of such fungicides as their availability in aqueous media is greatly increased. The condensation products formed relatively insoluble and often crystalline salts with many metallic ions. The precipitation of these salts was briefly considered from the analytical point of view. The condensations between the rhodanines and the benzaldehyde sulphonic acids were carried out in acid media and crystalline coloured products were obtained in good yield.In a series of papers14 from this department the syntheses of a variety of compounds of potential fungitoxicological value have been reported. The class of compounds obtained by the condensation of rhodanine or a 3-substituted congener with carbonylic compounds has been particularly studied. Rhodanine has been condensed with ali-

The condensation products of rhodanine, 3-ethylrhodanine, 3-phenylrhodanine, 3-allylrhodanine and 3-carboxymethylrhodanine with various substituted and unsubstituted pyridine and quinoline aldehydes have been prepared for bacterial and fungicidal evaluation. An earlier series of unsubstituted pyridylmethylene-rhodanines has thus been extended to include products substituted in either or both of the heterocyclic rings. Such substitution may enhance the already known fungicidal character of such rhodanine-aldehyde condensation products. The products obtained by the condensation of the quinoline aldehydes may be considered as substituted in a similar manner as the less accessible dialkylpyridine products and it is possible that these two types of compounds will show a similarity in biological activity. Condensations between the rhodanines and the aldehydes were carried out in acid medium and crystalline coloured condensation products were obtained in good yield.

More than three-quarters of a century has elapsed since antipyrine (Ia) was introduced into medicine by Knorr as an antipyretic and analgesic (1). Altllough pyrazolone analgesics have now virtually vanished from the scene in North America and the Scandinavian countries (2), they are still widely used in other areas and considerable efforts have been expended to improve their pharmacological properties (3, 4). 111 recent years seine of this effort has been focused on 4-antipyrinaldehyle (Ib)%and its derivatives (5-14), principally in connection wit11 antineuralgic and febrifugal effects. While insecticidal pyrazolones have been described (15-17), other nonanalgesic applications of 4-antipyrinaldehyde or its derivatives have received little attention other than brief reports of tuberculostatic (18) and bacteriostatic activity (10).