79307-66-7Relevant articles and documents
Synthesis of unexpected bifunctionalized thiazoles by nucleophilic attack on allenyl isothiocyanate
Jawabrah Al-Hourani, Baker,Richter, Frank,Vrobel, Kai,Banert, Klaus,Korb, Marcus,Rueffer, Tobias,Walfort, Bernhard,Lang, Heinrich
, p. 2899 - 2906 (2014/05/20)
Treatment of allenyl isothiocyanate with a variety of nucleophiles leads to 5-methylthiazoles with a functional group at the 2-position. The same pattern of reactivity is also seen with N-aminophthalimide. In the presence of azide salt, hydrazoic acid, or N,N-disubstituted hydroxylamines, however, allenyl isothiocyanate is converted into bifunctionalized thiazoles. We explain the formation of these products by nucleophilic addition at the isothiocyanato moiety followed by ring closure and an N-N or N-O cleavage reaction to generate short-lived 2-imino-5-methylidenethiazole or 5-methylidenethiazol-2-one. Such intermediates are trapped by addition reactions to give the final heterocyclic compounds. In the case of N,N-disubstituted hydroxylamines, the primary addition products with allenyl isothiocyanate can be detected as unstable intermediates by IR and NMR spectroscopy.
SYNTHESIS AND REACTIONS OF NEW VINYL ISOTHIOCYANATES
Banert, Klaus,Groth, Stefan,Hueckstaedt, Holger,Vrobel, Kai
, p. 323 - 324 (2007/10/02)
New vinyl isothiocyanates, which can be prepared from easily accessible thiocyanates by sigmatropic shifts, show unusually high reactivity used for the synthesis of heterocyclic sulfur compounds.
The Structures of 4- and 5-Substituted Δ4-Thiazolin-2-ones
Cornwell, Stephen P.,Kaye, Perry T.,Kent, Alexander G.,Meakins, G. Denis
, p. 2340 - 2343 (2007/10/02)
In order to establish the structures of compounds described as Δ4-thiazolin-2-ones ten sets of heterocycles (each comprising a 4- or 5-substituted Δ4-thiazolin-2-one, the N-methyl derivative, and the corresponding 2-methoxythiazole) have been examined by i.r., u.v., and 1H and 13C n.m.r. spectrometry.The i.r. results established that in solution the parent compounds exist entirely or predominantly as the 2-oxo-forms.This conclusion is supported by the 1H n.m.r. evidence, but the u.v. and 13C n.m.r. data do not give a clear distinction between the possible 2-oxo- and 2-hydroxy-structures.