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Regioselective N-functionalization of tetraazacycloalkanes
Authors:Boschetti Frédéric  Denat Franck  Espinosa Enrique  Tabard Alain  Dory Yves  Guilard Roger
Affiliation:Université de Bourgogne, Laboratoire d'Ingénierie Moléculaire pour la Séparation et les Applications des Gaz, LIMSAG UMR 5633, Faculté des Sciences Gabriel, 6 boulevard Gabriel, 21100 Dijon, France.
Abstract:[reaction: see text] Bisaminal type compounds obtained by condensation of pyruvic aldehyde with the suitable open-chain tetraamine followed by cyclization with either dibromoethane or dibromopropane can be regioselectively quaternized by a wide range of alkylating agents. Removal of the bisaminal bridge yields the monosubstituted tetraazamacrocycle or bismacrocycle. Further functionalization allows the preparation of bifunctional ligands or trisubstituted macrocycles. The structure of six compounds was solved by X-ray diffraction, and the unexpected results are rationalized according to the molecular modeling calculations.
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