Selenium‐Containing Heterocycles from Isoselenocyanates: Synthesis of 1,3‐Selenazinane and 1,3‐Selenazinanone Derivatives |
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| Authors: | Geoffroy L. Sommen 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?635?42?82;2. fax: 01?635?6836);3. Present address: Lonza AG, Walliser Werke, CH‐3930, Visp, Switzerland;4. Postdoctoral stay at the University of Zürich (08.2004–08.2005). |
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| 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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| Keywords: | Selenaheterocycles Isoselenocyanates 1,3‐Selenazines Cyclization reactions X‐Ray crystallography |
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