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Selenium-containing heterocycles from Isoselenocyanates: Synthesis of 1,3-Selenazinane and 1,3-Selenazinanone derivatives


Sommen, G L; Linden, A; Heimgartner, H (2007). Selenium-containing heterocycles from Isoselenocyanates: Synthesis of 1,3-Selenazinane and 1,3-Selenazinanone derivatives. Helvetica Chimica Acta, 90(3):472-487.

Abstract

The reaction of the intermediate ketene N,Se-hemiacetal 3, prepared from cyanomethylene derivatives 1 by treatment with Et3N and aryl isoselenocyanates 2, with bis-electrophiles 6, 7, 9, and 11 in DMF affords tetrahydro-1H-1,3-selenazine (= 1,3-selenazinane) derivatives 8, 10, and 12 in good yield (Scheme 2 and Tables 1 – 3). Chemical and spectroscopic evidence for the structures of the new compounds are described. The structures of 8d and 12e are established by X-ray crystallography (Figs. 1 and 2).

Abstract

The reaction of the intermediate ketene N,Se-hemiacetal 3, prepared from cyanomethylene derivatives 1 by treatment with Et3N and aryl isoselenocyanates 2, with bis-electrophiles 6, 7, 9, and 11 in DMF affords tetrahydro-1H-1,3-selenazine (= 1,3-selenazinane) derivatives 8, 10, and 12 in good yield (Scheme 2 and Tables 1 – 3). Chemical and spectroscopic evidence for the structures of the new compounds are described. The structures of 8d and 12e are established by X-ray crystallography (Figs. 1 and 2).

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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:08 Nov 2011 10:21
Last Modified:07 Dec 2017 09:31
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.200790051
Related URLs:http://www.zora.uzh.ch/65013/

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