Selenium‐Containing Heterocycles from Isoselenocyanates: 4‐Methylselenazole Derivatives from the Reaction with Malononitrile and Propargyl Chloride |
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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?4282;2. fax: +41?44?635?6812);3. Present address: Lonza Braine SA, Chaussée de Tubize 297, Batiment B8P2, B‐1420 Braine l'Alleud.;4. Postdoctoral stay at the University of Zürich (08.2004‐08.2005). |
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| Abstract: | Aryl isoselenocyanates 1 react with malononitrile ( 6a ) and propargyl chloride ( 8 ) in DMF in the presence of Et3N to give the corresponding 2‐(3‐aryl‐2,3‐dihydro‐4‐methyl‐1,3‐selenazol‐2‐ylidene)malononitriles 12 as major products. The analogous reaction takes place with benzoylacetonitrile ( 6f ) instead of 6a . In some cases, the corresponding noncyclic 2‐[(arylamino)(prop‐2‐ynylselanyl)methylidene]malononitriles 9 were obtained as minor products. The structures of 9e and 11a have been established by X‐ray crystallography. |
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| Keywords: | Isoselenocyanates Selenaheterocycles 1,3‐Selenazoles Malononitrile Propargyl chloride X‐Ray crystallography |
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