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

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, whic...

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Hauptverfasser: Bergemann, Marco (VerfasserIn) , Neidlein, Richard (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 1999
In: Helvetica chimica acta
Year: 1999, Jahrgang: 82, Heft: 6, Pages: 909-918
ISSN:1522-2675
DOI:10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T
Online-Zugang:Verlag, kostenfrei registrierungspflichtig, Volltext: http://dx.doi.org/10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T
Verlag, kostenfrei registrierungspflichtig, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T/abstract
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Verfasserangaben:by Marco Bergemann and Richard Neidlein
Beschreibung
Zusammenfassung: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.
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Beschreibung:Online Resource
ISSN:1522-2675
DOI:10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T

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