We describe a selective and efficient propargyl-allyl coupling reaction between 1,3-dilithiopro^argyLphenyl sulfide (1) and allylic halides to produce lithiated, 1,5enynes 2, which can be directly treated with Li in liquid ammonia in the presence of NaNH2 (~1 equiv) to produce cleanly 1,5-enynes in 70-80% overall yields (eq 1).Stereo-and regioselective synthesis of 1,5-dienes of terpenoid origin via cross-coupling has been achieved most commonly by the procedure of Biellmann and related allyl-allyl couplings.2 While these methods are satisfac-(1) Selective Carbon-Carbon Bond Formation via Transition Metal Catalysis. 23.
cis- and trans-2-(2,4,5-trimethoxyphenyl)cyclobutylamine and trans-2-(2,5-dimethoxy-4-methylphenyl)cyclobutylamine were synthesized as conformationally restricted analogues of hallucinogenic phenylisopropylamines. In rats trained to discriminate saline from LSD (0.08 mg/kg, ip) in a two-lever drug discrimination paradigm, no generalization of the LSD stimulus to the cis trimethoxy compound occurred at doses up to 20 mg/kg. For both of the trans compounds, partial generalization of the LSD cue occurred at doses of 5 mg/kg or greater. In contrast, complete generalization occurred with trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine. The ED50 for this compound and the doses of the trans cyclobutyl homologues at which significant drug-appropriate responding occurred indicate that the latter are on the order of 50-75 times less potent than the cyclopropylamine analogue. The lack of generalization to the cyclobutylamines indicates either that their discriminative stimulus properties differ from LSD or that they lack discriminative effects.
Aus den substituierten Anilinen (I), Thioglykolsäure (II) und dem Acetophenon (III) werden unter ZnCIQ‐Katalyse die 3‐Arylthjazolidinone (IV) erhalten und auf fungicide Wirkung untersucht.
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