N-Phenacyloxycarbamates and other systems containing a CH,-0-N= framework, in the presence of bases, undergo a CH,-0-N= --+ CH(0H)-N= rearrangement. The mechanism of this reaction has been studied kinetically and through crossover and capture experiments. The bulk of the data favours an intermolecular ionic mechanism which occurs by removal of a proton from the methylene group in the rate-determining step, followed by interaction between a glyoxal molecule and a carbamate anion in the fast step of the reaction.* a-Chloro-a-phenylacetophenone.
An efficient synthesis of methyl dl-cis-jasmonate is described, starting from the previously described 2-(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]cyclopentanone (3), itself easily prepared from succinyl chloride and methyl potassium malónate. Alkylation of 3 with l-bromo-2-pentyne followed by selective removal of the 2-carbomethoxy group gave dehydrojasmonic acid. On esterification and reduction (H2/ Pd/C/ pyridine) of the triple bond to the cis olefin, dehydrojasmonic acid afforded methyl dl-cis-jasmonate in 40% overall yield from succinyl chloride.
Die Phenacylbromide (I) reagieren mit dem 1‐Aminoisochinolin (II) in Gegenwart von Basen zu den Arylimidazoisochinolinen (III), die auch aus Isochinolin (V) und (I) über die Phenacylisochinoliniumbromide (IV) mit FeCl3/NH3 zugänglich sind.
Ausgehend von den Verbindungen (I), (VIII) bzw. (XIV) werden nach den aufgezeichneten Reaktionsfolgen die Oxazolylcarbonsäureamide (VII), (XIII) bzw. (XVI) synthetisiert und pharmakologisch untersucht.
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