1160293-82-2Relevant academic research and scientific papers
Synthesis of chiral polyazamacrocycles of variable ring size
Kamioka, Seiji,Sugiyama, Sakae,Takahashi, Takashi,Doi, Takayuki
experimental part, p. 2529 - 2536 (2010/07/16)
Synthesis and structure elucidation of optically active tri-, tetra-, and penta-azamacrocycles having 4-methoxyphenyl pendants are described. Regioselective ring opening of a nosylaziridine with secondary benzyl amines was repeatedly performed to afford the cyclization precursors. Intramolecular N-alkylation of N-(ω-haloalkyl) nosylamide provided tri-, tetra-, and penta-azamacrocycles. On the basis of our study of the tetra-azamacrocycle previously elucidated by X-ray single-crystal analysis and in solution by NMR analysis, we conclude that the tri-azamacrocycle does not mainly have a vase-type conformation because of the steric hindrance of the 4-methoxyphenyl groups but the penta-azamacrocycle has a vase-type conformation in CDCl 3 and in CD2Cl2. The vase-type conformation of the penta-azamacrocycle is, however, not as much stable as that observed in the tetra-azamacrocycle because conformational flexibility of the penta-azamacrocycle was observed in deuterated benzene. The Royal Society of Chemistry 2010.
Chiral tetraazamacrocycles having four pendant-arms
Kamioka, Seiji,Takahashi, Takashi,Kawauchi, Susumu,Adachi, Hiroaki,Mori, Yusuke,Fujii, Kotaro,Uekusa, Hidehiro,Doi, Takayuki
supporting information; experimental part, p. 2289 - 2292 (2009/10/02)
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. Sugarhybrid molecules 12a-12f were synthesized based on the scaffold 9. NMR study showed that 12a-12f keep the similar conformation as 9 in solution.
