A versatile strategy for the synthesis of crown ether-bearing heterocycles: discovery of calcium-selective fluoroionophore.
Heterocycles have been modified in various ways in the search for new functions, but few examples are known of crown ethers incorporating heterocycles in macro-ring systems. Here we report a simple and versatile synthesis of crown ether-bearing heterocycles. An acylurea moiety in the heterocycles is efficiently transformed to 'crown ether' of various ring sizes. The products included a Ca(2+)-selective fluoroionophore. Our simple methodology is expected to provide many novel functional heterocyclic compounds, including fluoroionophores and candidate pharmaceuticals.
Aoki
Yuko
Y
Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya, Aichi 467-8603, Japan.
Umezawa
Naoki
N
Asano
Yuko
Y
Hatano
Keiichiro
K
Yano
Yuki
Y
Kato
Nobuki
N
Higuchi
Tsunehiko
T
D002118:Calcium / Q000737:chemistry*; D043844:Crown Ethers / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007476:Ionophores / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism