Cosmosen: Octa-Armed 24-Membered Cyclic Octaamine Synthesized from a Byproduct in the Preparation of 4-Benzyl-2,6-dioxocyclen.

The Journal of Organic Chemistry
Huiyeong JuYoichi Habata

Abstract

The synthesis of an octa-armed 24-membered cyclic octaamine (1) is reported. When 4-benzyl-1,4,7,10-tetraazacyclododecane-2,6-dione (3a) was prepared by the reaction of diethylenetriamine with diethyl N-benzyliminodiacetate (2), a dimeric macrocycle (3b) was obtained as a byproduct in a 5% yield. An octa-armed 24-membered cyclic octaamine (1), named Cosmosen, was prepared via the reductive amination and reduction of 3b. The binding constants for the 1:1 and 2:1 (Ag+/1) complexation of 1 were estimated to be ca. 7.9 and 13.9, respectively, by titration experiments using UV-vis spectrometry in methanol and chloroform (v/v, 9:1) solutions at 298 K.

References

May 5, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Yoichi HabataShim Sung Lee
Jan 11, 2007·Chemical Reviews·Nataliya E BorisovaYuri A Ustynyuk
Jun 27, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·William LevasonMichael Webster
Aug 30, 2012·Organic Letters·Yoichi HabataShunsuke Kuwahara
Mar 2, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Yoichi HabataShunsuke Kuwahara
May 21, 2013·Organic & Biomolecular Chemistry·Yoichi HabataShunsuke Kuwahara
Nov 14, 2014·Angewandte Chemie·Hubert Schmidbaur, Annette Schier
Nov 22, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Yoichi HabataShunsuke Kuwahara
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Feb 24, 2015·Journal of the American Chemical Society·Hideyuki ShimizuMasahiko Iyoda
Jul 25, 2019·The Journal of Organic Chemistry·Assunta D'AmatoFrancesco De Riccardis
Feb 20, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Huiyeong JuYoichi Habata

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