- Chemical Behavior of N-Alkyl-N-methylbenzylammonium N-Alkylide
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N-Alkyl-N-methyl(4-substituted benzyl)ammonium N-alkylides (3), produced by fluoride ion induced desilylation of N-alkyl-N-methyl-N-(4-substituted benzyl)-1-(trimethylsilyl)alkylammonium iodides (2), were mainly converted into N-alkyl-N-methyl-1-(4-substituted benzyl)alkylamines (5, Stevens rearrangement products) and 4-substituted toluenes (8).Both compounds were produced via radical-forming and -destroying pathways from 2-substituted-6--5-methylene-1,3-cylohexadienes (4), which were initially formed from 3 by sigmatropic rearrangement.There is no direct migration pathway from 3 to 5.
- Okazaki, Seiji,Shirai, Naohiro,Sato, Yoshiro
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p. 334 - 337
(2007/10/02)
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- POTENTIAL ANTIDEPRESSANTS: 1-(4-(AMINOALKOXY)PHENYL)-2-PROPYLAMINES
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1-(4-Hydroxyphenyl)-2-propylamine (X) and its N-monomethyl (XI) and N,N-dimethyl (XII) derivatives were O-alkylated with six tert.aminoalkyl chlorides to aminoalkyl ethers Ia-VIc.In cases of X and XI the reactions were complicated by O,N-dialkylation leading to isolation of triamino ethers XVI and XVII. 1-(4-Hydroxyphenyl)propan-2-one was alkylated with 2-dimethylaminoethyl chloride and the ether XIII was obtained.An attempt to transform 4-(2-dimethylaminoethoxy)benzaldehyde to the 1-aryl-2-nitropropene XIV by heating with nitroethane in acetic acid in the presence of ammonium acetate resulted in the formation of 4-(2-dimethylaminoethoxy)benzonitrile (XV).In the form of salts the amino ethers prepared were tested for antidepressant activity but proved little active or inactive.
- Kmonicek, Vojtech,Vejdelek, Zdenek,Holubek, Jiri,Valchar, Martin,Protiva, Miroslav
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p. 1721 - 1733
(2007/10/02)
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