Abstract
Novel asymmetric macrocyclic Schiff bases were synthesized by the condensation of N,N′-bis(2-aminophenyl)-3,4-diphenylthiophene-2,5-dicarboxamide (1) with diformyl derivatives of phenol, furan, difurans, pyridine, pyrrole, and dipyrroles. The reaction proceeds in high yields and without by-products in methanol in the presence of inorganic and organic acids (proton-template condensation). In the case of monocyclic diformyl derivatives and di(5-formylfuran-2-yl) sulfide, the reaction occurs in 1,4-dioxane (templateless synthesis). The synthesized macrocycles were characterized by elemental analysis data and NMR and mass spectra.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
V. V. Roznyatovsky, N. E. Borisova, M. D. Reshetova, Yu. A. Ustynyuk, G. G. Aleksandrov, I. L. Eremenko, and I. I. Moiseev, Izv. Akad. Nauk, Ser. Khim., 2004, 1161 [Russ. Chem. Bull., Int. Ed., 2004, 53, 1208].
P. Guerriero, S. Tamburini, and P. A. Vigato, Coord. Chem. Rev., 1995, 139, 17.
H. Okawa, H. Furutachi, and D. Fenton, Coord. Chem. Rev., 1998, 174, 51.
J. L. Sessler, G. Hemmi, T. D. Mody, T. Murai, A. Burrell, and S. W. Young, Acc. Chem. Res., 1994, 27, 43.
V. Alexander, Chem. Rev., 1995, 95, 273.
J. L. Sessler, E. Kataev, G. D. Pantos, and Yu. A. Ustynyuk, Chem. Commun., 2004, 1276.
J. L. Sessler, S. Camiolo, and P. Gale, Coord. Chem. Rev., 2003, 240, 17.
N. E. Borisova, Yu. A. Ustynyuk, M. D. Reshetova, G. G. Aleksandrov, I. L. Eremenko, and I. I. Moiseev, Izv. Akad. Nauk, Ser. Khim., 2004, 326 [Russ. Chem. Bull., Int. Ed., 2004, 53, 340].
J. L. Sessler, M. R. Johnson, and V. Lynch, J. Org. Chem., 1987, 52, 4394.
J. L. Sessler, H. Maeda, T. Mizuno, V. M. Lynch, and H. Furuta, J. Am. Chem. Soc. 2002, 124, 13474.
N. W. Alcock, R. G. Kingstone, P. Moore, and C. Pierpoint, J. Chem. Soc., Dalton Trans., 1984, 1937.
G. Drechsler and G. Kopperschlager, J. Prakt. Chem., 1965, 27, 258.
K. Olsson and P. Pernemalm, Acta Chem. Scand., 1979, 33, 125.
G. Märkl, Th. Knott, P. Kreimeier, Th. Burgemeister, and F. Kastner, Tetrahedron, 1996, 52, 11763.
J. L. Sessler, J. Porphyrins Phthalocyanines, 2003, No. 7, 97.
Metody polucheniya khimicheskikh reaktivov i preparatov [Methods for Preparation of Chemical Reagents and Materials], Collection of Works, Issue 22, NIITEKhIM, Moscow, 1970 (in Russian).
J. L. Sessler and M. C. Hoehner, Synlett, 1994, 211.
H. J. Backer and W. Stevens, Recl. Trav. Chim. Pays-Bas, 1940, 59, 423.
Author information
Authors and Affiliations
Additional information
Dedicated to Academician N. S. Zefirov on the occasion of his 70th birthday.
For Part 6, see Ref. 1.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2152–2156, September, 2005.
Rights and permissions
About this article
Cite this article
Roznyatovsky, V.V., Borisova, N.E., Reshetova, M.D. et al. Binuclear and polynuclear transition metal complexes with macrocyclic ligands 7. Directed step-by-step synthesis of novel unsymmetric macrocyclic ligands. Russ Chem Bull 54, 2219–2223 (2005). https://doi.org/10.1007/s11172-006-0100-y
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0100-y