Curtius Rearrangement of ω-Azido Acid Chlorides: Access to the Corresponding ω-Azido Substituted Amines and Carbamates, Useful Building Blocks for Polyamine Syntheses

Mostafa Khoukhi; Michel Vaultier; Aziza Benalil; Bertrand Carboni

doi:10.1055/s-1996-4438

Synthesis 1996; 1996(4): 483-487
DOI: 10.1055/s-1996-4438

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Curtius Rearrangement of ω-Azido Acid Chlorides: Access to the Corresponding ω-Azido Substituted Amines and Carbamates, Useful Building Blocks for Polyamine Syntheses

Mostafa Khoukhi, Michel Vaultier¹ , Aziza Benalil, Bertrand Carboni²

¹Groupe de Recherche de Physicochimie Structurale, URA CRNS 704, Université de Rennes 1, Campus de Beaulieu, F-35042 Rennes Cedex, France, Fax +33(99)286955
²Groupe de Recherche de Physicochimie Structurale, URA CRNS 704, Université de Rennes 1, Campus de Beaulieu, F-35042 Rennes Cedex, France, Fax +33(99)286955, E-mail bertrand.carboni@univ-rennes1.fr

Abstract

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Treatment of ω-azido acid chlorides with trimethylsilyl azide affords ω-azido isocyanates which can be easily converted in good yields to the corresponding ω-azidoamines or ω-azidocarbamates. 1,3- and 1,4-Diamine dihydrochlorides can then be prepared by catalytic hydrogenation or reductive alkylation with an organodichloroborane.

Curtius rearrangement - azides - diamines

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