Archiv der Pharmazie p. 215 - 220 (1980)
Update date:2022-08-03
Topics:
Wolff, Hans-Michael
Hartke, Klaus
Alkylation of N,N'-dimethylbenzamidine (4) with chloromethyl methyl ether and allyl iodide leads to the formation of the N-trisubstituted amidines 5a and 5d; the lithium salt of 4 yields 5b and 5c with chloromethyl methyl sulfide and (chloromethyl)diethylamin, respectively.At temperatures up to 175 deg C no <1,3>sigmatropic rearrangement can be detected by (1)H-NMR spectroscopy; below room temperature a hindered rotation around the C-N single bond is observed.
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Doi:10.1248/cpb.33.4732
(1985)Doi:10.1021/acs.orglett.9b00263
(2019)Doi:10.1016/j.tet.2018.01.022
(2018)Doi:10.1246/bcsj.40.2375
(1967)Doi:10.1021/jo01308a014
(1980)Doi:10.1055/s-1998-1818
(1998)