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


Zhou, Y; Linden, A; Heimgartner, H (2011). Reactions of Imidoyl Isoselenocyanates with Aromatic 2-Amino N-Heterocycles and 1-Methyl-1H-imidazole. Helvetica Chimica Acta, 94(9):1575-1585.

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-4l4-[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.

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-4l4-[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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis
Language:English
Date:September 2011
Deposited On:10 Oct 2011 09:19
Last Modified:18 Aug 2018 00:55
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
OA Status:Green
Publisher DOI:https://doi.org/10.1002/hlca.201100230

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