Strategies for the Regioselective N-Functionalization of Tetraazacycloalkanes. From Cyclam and Cyclen Towards More Sophisticated Molecules

F. Denat; S. Brandès; R. Guilard

doi:10.1055/s-2000-6589

Synlett 2000; 2000(5): 0561-0574
DOI: 10.1055/s-2000-6589

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Strategies for the Regioselective N-Functionalization of Tetraazacycloalkanes. From Cyclam and Cyclen Towards More Sophisticated Molecules

F. Denat^* , S. Brandès, R. Guilard

^*Laboratoire d'Ingénierie Moléculaire pour la Séparation et les Applications des Gaz, LIMSAG UMR 5633, Faculté des Sciences Gabriel, 6, Bd Gabriel - 21100 Dijon, France; E-mail: limsag@u-bourgogne.fr

Abstract

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Different approaches for the selective N-substitution of tetraazacycloalkanes and more specifically cyclam and cyclen are reported. The N-functionalization can be performed either before or after cyclization, and various protecting groups might be used to discriminate one, two or three nitrogen atoms. For example, tert-butyloxycarbonyl (Boc) appears to be a very convenient protecting group since it can be removed under mild conditions. trans-Disubstituted macrocycles are easily prepared by using trans-dioxotetraazacycloalkanes or a cyclam containing a bisaminal moiety as the starting material. These precursors allow for the synthesis of preorganized molecules such as cryptands and macrotricycles in relatively large scale and in very decent yields.

tetraazamacrocycles - regioselectivity - protecting groups - N-substitution - cryptands

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