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Syntheses and reactions of 1-amino-2,2-dialkylcyclopropane-1-carbonitriles and -carboxamides - Potential precursors of ACC derivatives

par Aelterman, Wim;Tehrani, Kourosch Abbaspour;Coppens, Wim;Huybrechts, Tom;De Kimpe, Norbert;Tourwe, Dirk ;Declercq, Jean-Paul
Référence European Journal of Organic Chemistry, 1999, 1, page (239-250)
Publication Publié, 1999-01

Article révisé par les pairs

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Résumé :

The direct cyclization of 2-amino-4-chloro,3,3-dimethylbutanenitrile with potassium tert-butoxide in THF afforded 1-amino-2,2- dimethylcyclopropane-1-carbonitrile and a dimerization product. Various new cis- and trans-1-(tert-butylamino)-2-benzyl-2-methylcyclopropane- carbonitriles and the corresponding cyclopropanecarboxamides have been synthesized, with focus on the isolation of the pure stereoisomeric cyclopropanecarboxamides. The relative configuration of the stereoisomers was established by X-ray crystallographic analysis of one of the model compounds. A new route to the latter functionalized cyclopropanes was developed by reaction of 1-methoxycyclopropylamines with potassium cyanide. Some remarkable rearrangements of 1-aminocyclopropane-1-carbonitriles into azetidine and oxazine derivatives via Favorskil-derived intermediates are reported. Various aspects of the chemistry of geminally functionalized cyclopropanes are discussed.