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Selenium-Containing heterocycles from isoselenocyanates: synthesis of 5-Amino-2,4-dihydro-3H-1,2,4-triazole-3-selones


Sommen, G L; Linden, A; Heimgartner, H (2007). Selenium-Containing heterocycles from isoselenocyanates: synthesis of 5-Amino-2,4-dihydro-3H-1,2,4-triazole-3-selones. Helvetica Chimica Acta, 90(4):641-651.

Abstract

The reaction of S-methylisothiosemicarbazide hydroiodide (= S-methyl hydrazinecarboximidothioate hydroiodide; 1), prepared from thiosemicarbazide by treatment with MeI in EtOH, and aryl isoselenocyanates 5 in CH2Cl2 affords 3H-1,2,4-triazole-3-selone derivatives 7 in good yield (Scheme 2, Table 1). During attempted crystallization, these products undergo an oxidative dimerization to give the corresponding bis(4H-1,2,4-triazol-3-yl) diselenides 11 (Scheme 3). The structure of 11a was established by X-ray crystallography.

Abstract

The reaction of S-methylisothiosemicarbazide hydroiodide (= S-methyl hydrazinecarboximidothioate hydroiodide; 1), prepared from thiosemicarbazide by treatment with MeI in EtOH, and aryl isoselenocyanates 5 in CH2Cl2 affords 3H-1,2,4-triazole-3-selone derivatives 7 in good yield (Scheme 2, Table 1). During attempted crystallization, these products undergo an oxidative dimerization to give the corresponding bis(4H-1,2,4-triazol-3-yl) diselenides 11 (Scheme 3). The structure of 11a was established by X-ray crystallography.

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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
Language:English
Date:2007
Deposited On:04 Nov 2011 13:29
Last Modified:07 Dec 2017 09:30
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Dr. Helmut Legerlotz Foundation, Zürich, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200790067

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