Premium
Zur Synthese und Dimroth‐Umlagerung von 4‐(Dialkylamino)‐2 H ‐1,3,5‐oxadiazin‐2‐thionen
Author(s) -
Spitzner Roland,
Andersch Jörg,
Schroth Werner
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890245
Subject(s) - chemistry , potassium thiocyanate , medicinal chemistry , trimethylsilyl , isocyanide , acetic acid , thiocyanate , organic chemistry
Concerning the Synthesis and the Dimroth Rearrangement of 4‐(Dialkylamino)‐2 H ‐1,3,5‐oxadiazine‐2‐thiones The title compounds 3 are readily obtained by reaction of N,N ‐dialkylchloroformamidines 2 with potassium thiocyanate. The amidines 2 can be prepared profitably from isocyanide dichlorides 1 with the aid of N ‐(trimethylsilyl)dialkylamines. The thiones 3 behave very sensitively towards acids and are rearranged completely to 4‐(dialkylamino)‐2 H ‐1,3,5‐thiadiazin‐2‐ones 4 by treatment with acetic acid.