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

✍ Scribed by YuehuiDong Zhou; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
324 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The reaction of N‐phenylimidoyl isoselenocyanates 1 with 2‐amino‐1,3‐thiazoles 10 in acetone proceeded smoothly at room temperature to give 4__H__‐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 3__H__‐4λ^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‐1__H__‐imidazole (12) and 1 led to 3‐methyl‐1‐(N‐phenylbenzimidoyl)‐1__H__‐imidazolium selenocyanates 15 (Scheme 4). In all three cases, an initially formed selenourea derivative is proposed as an intermediate.

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