Synthesis of a C-3 -symmetric tris-imine via dynamic covalent bond formation between a trialdehyde and a triamine

Dynamic covalent chemistry is an effective technique for the preparation of complex organic compounds. We succeeded in synthesizing a cage-shaped compound through the aggregation of two types of functional molecules. More specifically, a tris-imine 5 was quantitatively obtained by reacting a C-3-sym...

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Bibliographic Details
Published inTetrahedron letters Vol. 58; no. 49; pp. 4612 - 4616
Main Authors Nakada, Keiko, Kondo, Seiya, Matsumoto, Yoshiteru, Yamanaka, Masamichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 06.12.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RECEPTOR
Cages
Dynamic covalent chemistry
Supramolecular chemistry
Self-assembly
RESONANCE MASS-SPECTROMETRY
Imines
MOLECULAR RECOGNITION
CONSTRUCTION
CAPSULE
CHEMISTRY
BOROXINE
BINDING
UREA
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Summary:Dynamic covalent chemistry is an effective technique for the preparation of complex organic compounds. We succeeded in synthesizing a cage-shaped compound through the aggregation of two types of functional molecules. More specifically, a tris-imine 5 was quantitatively obtained by reacting a C-3-symmetric trialdehyde 1 with a triamine 4 in acetonitrile in the presence of a trifluoroacetic acid catalyst. We also achieved the synthesis of the corresponding triamine 9 and the acetylated derivative 10 through reduction of the tris-imine C=N double bonds and subsequent acetylation. (C) 2017 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2017.10.061