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Reactions of Imidoyl Isoselenocyanates with Aromatic 2-Amino N-Heterocycles and 1-Methyl-1H-imidazole

  作者 Zhou, YH; Linden, A; Heimgartner, H  
  选自 期刊  Helvetica Chimica Acta;  卷期  2011年94-9;  页码  1575-1585  
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[摘要]The reaction of N-phenylimidoyl isoselenocyanates 1 with 2-amino-1,3-thiazoles 10 in acetone proceeded smoothly at room temperature to give 4H-1,3-thiazolo[3,2-a] [1,3,5]triazine-4-selones 13 in fair yields (Scheme 2). Under the same conditions, 1 and 2-amino-3-methylpyridine (11) underwent an addition reaction, followed by a spontaneous oxidation, to yield the 3H-4 lambda(4)-[1,2,4]selenadiazolo[1',5':1,5][1,2,4]selenadiazolo[2,3-a]pyridine 14 (Scheme 3). The structure of 14 was established by X-ray crystallography (Fig. 1). Finally, the reaction of 1-methyl-1H-imidazole (12) and 1 led to 3-methyl-1-(N-phenylbenzimidoyl)-1H-imidazolium selenocyanates 15 (Scheme 4). In all three cases, an initially formed selenourea derivative is proposed as an intermediate.

 
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