Rearrangement Reactions; 14: [1] Synthesis of Functionalized Thiazoles via Attack of Heteroatom Nucleophiles on Allenyl Isothiocyanates

Abstract

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 thiazole-2-phosphonates prepared by the same strategy using dialkyl or diphenyl phosphites as nucleophiles.

Key words

allenes - isothiocyanates - addition reactions - ring closure - heterocycles

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