TY - JOUR
T1 - Syntheses of large-membered macrocycles having multiple hydrogen bonding moieties
AU - Shimakoshi, Hisashi
AU - Kai, Takayuki
AU - Aritome, Isao
AU - Hisaeda, Yoshio
N1 - Funding Information:
We thank Professor K. Sakata, Kyushu Institute of Technology, for measurements of FAB mass spectra. This work was partially supported by Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
PY - 2002/11/11
Y1 - 2002/11/11
N2 - New macrocyclic compounds have been synthesized by Schiff-base condensation reaction with methylenebis(4,4′-methyl-6,6′-salicylaldehyde) and 1,2-bis(2-aminoethoxy)ethane based on a high dilution method. [2+2], [3+3], and [4+4]-Cyclocondenced products were effectively isolated and characterized by 1H NMR and HR mass (FAB) spectroscopies as well as X-ray analyses. Reduction of the macrocycles with NaBH4 afforded the corresponding multi-amino, multi-phenolic macrocyclic compounds. The reduced molecules have low energy barriers for conformation change, which are estimated by variable-temperature (VT) 1H NMR study.
AB - New macrocyclic compounds have been synthesized by Schiff-base condensation reaction with methylenebis(4,4′-methyl-6,6′-salicylaldehyde) and 1,2-bis(2-aminoethoxy)ethane based on a high dilution method. [2+2], [3+3], and [4+4]-Cyclocondenced products were effectively isolated and characterized by 1H NMR and HR mass (FAB) spectroscopies as well as X-ray analyses. Reduction of the macrocycles with NaBH4 afforded the corresponding multi-amino, multi-phenolic macrocyclic compounds. The reduced molecules have low energy barriers for conformation change, which are estimated by variable-temperature (VT) 1H NMR study.
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U2 - 10.1016/S0040-4039(02)02022-1
DO - 10.1016/S0040-4039(02)02022-1
M3 - Article
AN - SCOPUS:0037064511
SN - 0040-4039
VL - 43
SP - 8261
EP - 8264
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 46
ER -