Reactions of Imidoyl Isoselenocyanates with Aromatic 2‐Amino N‐Heterocycles and 1‐Methyl‐1H‐imidazole |
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Authors: | Anthony Linden Heinz Heimgartner |
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Affiliation: | 1. Organisch‐Chemisches Institut der Universit?t Zürich, Winterthurerstrasse 190, CH‐8057 Zürich, (phone: +41‐44‐6354282;2. fax: +41‐44‐6356812) |
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Abstract: | 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‐4λ4‐[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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Keywords: | Isoselenocyanates Selenourea 1H‐Imidazole, 1‐methyl‐ X‐Ray crystallography 1,3‐Thiazole, 2‐amino‐ Pyridine, 2‐amino‐3‐methyl‐ |
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