79307-66-7Relevant academic research and scientific papers
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.
Rearrangement reactions; 14: Synthesis of functionalized thiazoles via attack of heteroatom nucleophiles on allenyl isothiocyanates
Banert, Klaus,Al-Hourani, Baker Jawabrah,Groth, Stefan,Vrobel, Kai
, p. 2920 - 2926 (2007/10/03)
Treatment of allenyl isothiocyanates with sulfur-, oxygen-, nitrogen- or hydride-containing nucleophiles such as propane-2-thiol, thiophenol, hydrogen sulfide, alcohols, phenol or aqueous NaOH, NH3, primary or secondary aliphatic or aromatic amines, N,N,N′,N′-tetramethylguanidine or sodium cyanoborohydride resulted in ring closure to generate thiazoles bearing a functionality at position C-2 in most cases. Moreover, we report the first examples of aromatic miazole-2-phosphonates prepared by the same strategy using dialkyl or diphenyl phosphites as nucleophiles. Georg Thieme Verlag Stuttgart.
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.
