Modular synthesis of triaroylbenzene-derived crownophanes

作者: F. Christopher Pigge , Fatemeh Ghasedi , Angela V. Schmitt , Mayuri K. Dighe , Nigam P. Rath

DOI: 10.1016/J.TET.2005.03.072

关键词:

摘要: Abstract An isomeric series of homologous crownophanes (i.e., macrocycles possessing structural features crown ethers and cyclophanes) has been prepared via a concise modular synthetic route. Macrocyclization is achieved in reasonable yield during the course an enaminone-triggered benzannulation with bis(aryl ethynyl ketone) reaction partners. The examined were active alkali cation binding agents gas phase, but failed to exhibit ionophoric properties solution. On basis X-ray crystallographic analysis, it concluded that cyclophane framework these too large rigid allow efficient interaction cations examined.

参考文章(33)
Seiichi Inokuma, Shigefumi Sakai, Jun Nishimura, Syntheses and ionophoric properties of crownophanes Springer Berlin Heidelberg. pp. 87- 118 ,(1994) , 10.1007/BFB0025268
Kristin Bowman-James, Enrique García-España, Antonio Bianchi, Supramolecular chemistry of anions Wiley-VCH. ,(1997)
Jean-Marie Lehn, JL Atwood, JED Davies, DD MacNicol, F Vögtle, Comprehensive Supramolecular Chemistry ,(1996)
George W Gokel, Crown Ethers and Cryptands ,(1991)
Naohiro Kameta, Kazuhisa Hiratani, Yoshinobu Nagawa, A novel synthesis of chiral rotaxanes via covalent bond formation Chemical Communications. pp. 466- 467 ,(2004) , 10.1039/B314744D
Esther C. Kempen, Jennifer S. Brodbelt, A method for the determination of binding constants by electrospray ionization mass spectrometry Analytical Chemistry. ,vol. 72, pp. 5411- 5416 ,(2000) , 10.1021/AC000540E
Jun Nishimura, Seiichi Inokuma, Takashi Funaki, Daisuke Hara, Synthesis and Complexing Properties of Crownophanes Possessing Carboxyl Group Heterocycles. ,vol. 63, pp. 333- 346 ,(2004) , 10.3987/COM-03-9955
Yoshinobu Nagawa, Naoki Fukazawa, Jun-ichi Suga, Michael Horn, Hideo Tokuhisa, Kazuhisa Hiratani, Kunihiro Watanabe, Stepwise synthesis of crownophanes having either one or two hydroxy groups via Claisen rearrangement Tetrahedron Letters. ,vol. 41, pp. 9261- 9265 ,(2000) , 10.1016/S0040-4039(00)01681-6
Andrew C. Benniston, Patrick Gunning, Robert D. Peacock, Synthesis and binding properties of hybrid cyclophane-azamacrocyclic receptors. Journal of Organic Chemistry. ,vol. 70, pp. 115- 123 ,(2005) , 10.1021/JO048621O