Collect. Czech. Chem. Commun.
2002, 67, 609-621
https://doi.org/10.1135/cccc20020609
Regio- and Stereoselectivity in Preparation of Benzene Bridged Bis- and Tris-Tröger's Bases
Martin Valíka, Bohumil Dolenskya, Hana Petříčkováb and Vladimír Krála,*
a Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b Department of Solid State Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
Abstract
Synthetic strategy for novel multiple Tröger's base derivatives is presented. Compounds were prepared in three steps: o-nitrobenzoylation of benzene-1,2- and -1,3-diamines 3 followed by reduction of nitro and amide groups to amino functions and treatment of the obtained tetraamine compounds 6 with formaldehyde lead to simultaneous formation of bis-Tröger's base (bisTB) derivatives 7a, 7b. Only products of 1,2,3,4-substituted regioisomers with anti conformation were separated from reaction mixtures. The same synthetic procedure was used for preparation of tris-Tröger's base (trisTB) derivative 12b starting from benzene-1,3,5-triamine (8).
Keywords: Tröger's bases; Receptors; Tweezers; Amines; Supramolecular chemistry.
References: 22 live references.
