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.
A series of 3,5-diaryl-s-triazoles were synthesized and evaluated as postimplantation contragestational agents. The introduction of various substituents (e.g., an o-alkyl chain on one phenyl and a m-alkoxy group on the other) was found to increase the potency. Several compounds with very high pregnancy-terminating activity in both hamsters and rats were obtained. One of these, 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-s-triazole, DL 111 (36), was selected for detailed evaluation in various animal species. A synthetic scheme for the preparation of these compounds and preliminary structure-activity relationships are presented.
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.
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