Studies on the reactivity of α-cyano-α-isocyanoalkanoates - versatile synthons for the assembly of imidazoles

• Verfasst von: Bergemann, Marco [VerfasserIn]
• Verfasst von: Neidlein, Richard [VerfasserIn]
• Titel: Studies on the reactivity of α-cyano-α-isocyanoalkanoates - versatile synthons for the assembly of imidazoles
• Verf.angabe: by Marco Bergemann and Richard Neidlein
• Jahr: 1999
• Umfang: 9 S.
• Fussnoten: Gesehen am 28.04.2017
• Titel Quelle: Enthalten in: Helvetica chimica acta
• Ort Quelle: New York, NY : Wiley-VCH, 1918
• Jahr Quelle: 1999
• Band/Heft Quelle: 82(1999), 6, Seite 909-918
• ISSN Quelle: 1522-2675
• DOI: doi:10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 155767647X

Abstract

The reactivity and the synthetic potential of α-cyano-α-isocyanoalkanoates 2 were investigated. Interestingly, reaction of 2 with alkoxides gave (alkoxy)(alkyl)imidazoles 5, whereas the analogous thiolates led to different products, namely substituted 4H-imidazoles 7, together with compounds 6, which formed by addition of thiolate to the isocyano group. Primary amines reacted, on one hand, in the same manner as thiolates to form of 4H-imidazoles 10, and, on the other hand, cleavage of the molecule to the proposed unstable aminoimidazole 8 and the carbamate 9 was observed. Secondary amines add selectively to the isocyano group to form compounds 11. Like simple isocyanides, α-cyano-α-isocyanoalkanoates 2 can be subjected to [4+1] cycloadditions and multicomponent reactions of the Passerini type. Mechanisms for the described reactions are discussed.