Convenient methods for the synthesis of 1-substituted 3-adamantyl chlorides and bromides (2), 1-adamantylphenols and -cresols (3), and 1-adamantylacetic (6) as well as 1,3-adamantanediacetic (11) acids are described. Several novel derivatives were synthesized from these key intermediates: adamantylcyclohexanols (4) and -cyclohexanones (5) from adamantylphenols (3), and esters (7,12, and 22), amides (13 and 18), thioamides (9 and 16), amidine (10), nitrile (15), and amines (14 and 17) from 1-adamantanecarboxylic (19) and -acetic (6) acids and 1,3-adamantanediacetic acid (11). Some adamantylpyrimidines (24) and -purines (25 and 26) were also prepared. Antiviral activities of the compounds obtained in this work and a series of new 1-adamantyl alkyl ketones synthesized before, together with those of some known adamantane derivatives, were tested in vitro on monolayer culture of chick ambryo fibroblasts against Newcastle disease virus.
A convenient and economical procedure for synthesis of long‐chain 1‐O‐alkyl glyceryl ethers (V) is described. Alkyl glycidyl ethers (II) which were derived from the reaction of alcohols (I) with epichlorohydrin using a phase transfer catalyst were first converted into the corresponding dioxolanes (III) or 1‐O‐alkyl‐2,3‐di‐O‐acetylglycerols (IV). Subsequent hydrolysis of the resultant products provided 1‐O‐alkyl glyceryl ethers (V) in high yields.
Hydrogenation of carboxylic acids to alcohols at low temperature and under low pressure was achieved by using a new catalyst system, a rhenium‐osmium bimetallic catalyst. The most active catalyst was prepared by the reductionof the corresponding metal oxides with hydrogen in the presence of succinic acid. Decanoic acid was hydrogenated to decanol in high conversions at 25∼100 atm and 100∼120°C. Decane was formed as a by‐product by overreduction of the alcohol. The selectivity of alcohol was improved by the addition of thiophene as a modifier of the catalyst.
The four different kinds of bridgehead positions of 2,4-ethanoadamantane (1) exhibit different reactivities. Bromination with liquid bromine gave a mixture of 1-bromoand 6-bromoethanoadam an tañes. Structural assignments were made by 13C NMR, by conversion of the bromides to the corresponding alcohols and methyl derivatives, and by independent synthesis of the remaining bridgehead methylethanoadamantane isomers.
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