Chiral tetraazamacrocycles having four pendant-arms

Seiji Kamioka; Takashi Takahashi; Susumu Kawauchi; Hiroaki Adachi; Yusuke Mori; Kotaro Fujii; Hidehiro Uekusa; Takayuki Doi

doi:10.1021/ol9005954

Chiral tetraazamacrocycles having four pendant-arms

Org Lett. 2009 Jun 4;11(11):2289-92. doi: 10.1021/ol9005954.

Authors

Seiji Kamioka¹, Takashi Takahashi, Susumu Kawauchi, Hiroaki Adachi, Yusuke Mori, Kotaro Fujii, Hidehiro Uekusa, Takayuki Doi

Affiliation

¹ Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro, Tokyo 152-8552, Japan.

PMID: 19432409
DOI: 10.1021/ol9005954

Abstract

A chiral tetraazamacrocycle 9 having four pendant-arms was synthesized by repeating ring opening of an Ns-aziridine with secondary amines, followed by macrocyclization. The structure of 9 has been determined by single crystal X-ray diffraction analysis and NMR studies. Sugar-hybrid molecules 12a-12f were synthesized based on the scaffold 9. NMR study showed that 12a-12f keep the similar conformation as 9 in solution.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemistry
Aza Compounds / chemical synthesis*
Aza Compounds / chemistry
Aziridines
Crystallography, X-Ray
Macrocyclic Compounds / chemical synthesis*
Macrocyclic Compounds / chemistry
Magnetic Resonance Spectroscopy
Models, Chemical
Molecular Conformation
Molecular Structure
Stereoisomerism

Substances

Amines
Aza Compounds
Aziridines
Macrocyclic Compounds
aziridine