A Sonogashira cross-coupling/5-exo-dig cyclization/ionic hydrogenation sequence: synthesis of 4-substituted 3-azabicyclo[3.1.0]hexan-2-ones from 2-iodocyclopropanecarboxamides

A variety of 4-substituted 3-azabicyclo[3.1.0]hexan-2-ones have been prepared from 2-iodocyclopropanecarboxamides by a three-step sequence involving a copper-free Sonogashira coupling with terminal aryl- or heteroarylalkynes, followed by a 5-exo-dig cyclization and an ionic hydrogenation.

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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2013-06, Vol.78 (11), p.5794-5799
Hauptverfasser:	de Carné-Carnavalet, Benoît, Meyer, Christophe, Cossy, Janine, Folléas, Benoît, Brayer, Jean-Louis, Demoute, Jean-Pierre
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkynes - chemistry Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Cyclization Cyclopropanes - chemistry Hydrogenation Ions - chemistry Molecular Conformation
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Beschreibung
Zusammenfassung:	A variety of 4-substituted 3-azabicyclo[3.1.0]hexan-2-ones have been prepared from 2-iodocyclopropanecarboxamides by a three-step sequence involving a copper-free Sonogashira coupling with terminal aryl- or heteroarylalkynes, followed by a 5-exo-dig cyclization and an ionic hydrogenation.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo400713u