Synthesis of Dialkyl[1-allyl(3-alpha-naphthylprop-2-ynyl)]amine and -piperidine, Study of the Behaviour of Dialkylallyl(or propargyl)[1-allyl(3-alpha-naphthylprop-2-ynyl]ammonium and -piperidinium Bromides in Relation to a Base
A. S. MKRTCHYAN
Scientific Technological Centre of Organic and Pharmaceutical Chemistry of the NAS of the Republic of Armenia, Institute of Organic Chemistry, Yerevan, the Republic of Armenia
Keywords: -[1-allyl(3-alpha-naphthylprop-2-inyl)]amines, -allyl[1-allyl(3-alpha-naphthylprop-2-inyl)]ammonium bromides, dimethyl-1-allyl-3a, 4-dihydronaphtho[f]isoindolinium- and -piperidinium bromides, base catalyzed cyclization
Pages: 106-112
Abstract
Dimethyl-, diethyl[1-allyl(3-α-naphthylprop-2-ynyl)]ammonium and -piperidinium bromides were synthesized by alkylation of dimethyl-, diethyl[1-allyl(3-α-naphthylprop-2-ynyl)]amines and -piperidine, obtained by Stevens rearrangement of dimethyl-, diethylallyl(3-α-naphthylprop-2-ynyl)]ammonium and -piperidinium bromides, with allyl or propargyl bromides. 2,2-Dimethyl-, 1-allyl-3 a ,4-dihydronaphtho[ f ]piperidinium bromides were obtained through base-catalyzed cyclization of dimethylallyl[1-allyl(3-α-naphthylprop-2-ynyl)]ammonium and -piperidinium bromides in the yields of 90 and 88 %, respectively. It is shown that the interaction of propargyl analogs with a catalytic amount of the base leads to the formation of compounds of unknown structure.
DOI: 10.15372/CSD2022364
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