Premium
Imidazoline‐4‐thiones from cyanothioformamides and aldehyde imines: Formation, aromatization, and acetylation
Author(s) -
ElSharief Ahmed M. Sh.,
Ketcham Roger,
Ries Monika,
Schaumann Ernst,
Adiwidjaja Gunadi
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.333
Subject(s) - chemistry , aromatization , imine , aldehyde , acetylation , sulfur , disulfide bond , imidazolidine , carbon disulfide , ethanol , organic chemistry , medicinal chemistry , catalysis , biochemistry , gene
The reaction of N ‐methyl‐ ( 3a ) or N ‐phenylcyanothioformamide ( 3b ) with acetaldimine ( 5a , as 1‐amino‐1‐ethanol) gives 5‐(amino)imidazolidine‐4‐thiones 6B . Product 6a reacts with a second equivalent of 3a to give 8 which in turn is oxidized to disulfide 9 . Using araldimines 5b , 5c , only 1:2 intermediates 10 derived from 3a , 3b and two moles of the imine 5 are formed, but proved to be easily oxidized to disulfides 11 . Acetylation of 6 occurs chemoselectively on the exocyclic nitrogen and finally also on the thione sulfur to give 14 via 13 . J. Heterocyclic Chem., (2010).