Synthetic and crystallographic studies on pyridinophanes

被引:35
作者
Gryko, DT
Piatek, P
Pecak, A
Palys, M
Jurczak, J
机构
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
[2] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland
关键词
D O I
10.1016/S0040-4020(98)00385-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Eight macrocyclic bisamides and tetramides have been synthesized by reaction of dimethyl pyridine-2,6-dicarboxylate 1 with alpha,omega-diaminoethers in methanol as a solvent. Relationship between structure of an amine used and a ratio of bisamide to tetramide has been investigated. The X-ray structure of macrocyclic amides 8, 9, 14 and linear amide 16 are reported. They show intramolecular hydrogen bond patterns within macrocyclic cavities involving N-Py... NHamide, and in the cases of 9, 14 and 16, neutral molecules of water. Stability constants of selected ligands were measured using voltammetry. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7505 / 7516
页数:12
相关论文
共 39 条
[11]   COMPLEXATION OF DIVALENT AND TRIVALENT NICKEL AND COPPER IONS BY RIGID AND FLEXIBLE DIOXO TETRAAZA MACROCYCLES [J].
FABBRIZZI, L ;
KADEN, TA ;
PEROTTI, A ;
SEGHI, B ;
SIEGFRIED, L .
INORGANIC CHEMISTRY, 1986, 25 (03) :321-327
[12]   Synthesis of macrocyclic amides and their intermediate 2:1 and 3:2 reaction compounds from diethyl oxalate and ethereal oxygen-containing diamines [J].
Fukada, N ;
Ohtsu, T ;
Miwa, M ;
Mashino, M ;
Takeda, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (05) :1397-1401
[13]   PHOTOSENSITIZED PYRIMIDINE DIMER SPLITTING BY A METHOXYINDOLE BOUND TO A DIMER-RECOGNIZING MACROCYCLE [J].
GOODMAN, MS ;
ROSE, SD .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3268-3270
[14]   The synthesis of macrocyclic diamides and tetramides containing phenol units [J].
Gryko, DT ;
Piatek, P ;
Jurczak, J .
TETRAHEDRON, 1997, 53 (23) :7957-7966
[15]   New pyridino-18-crown-6 ligands containing two methyl, two tert-butyl, or two allyl substituents on chiral positions next to the pyridine ring [J].
Habata, Y ;
Bradshaw, JS ;
Young, JJ ;
Castle, SL ;
Huszthy, P ;
Pyo, T ;
Lee, ML ;
Izatt, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8391-8396
[16]   NOVEL MOLECULAR SCAFFOLDS - FORMATION OF HELICAL SECONDARY STRUCTURE IN A FAMILY OF OLIGOANTHRANILAMIDES [J].
HAMURO, Y ;
GEIB, SJ ;
HAMILTON, AD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (04) :446-448
[17]   FORMATION OF COMPLEXES BETWEEN AZA DERIVATIVES OF CROWN ETHERS AND PRIMARY ALKYLAMMONIUM SALTS .4. DIAZA-18-CROWN-6 DERIVATIVES [J].
HODGKINSON, LC ;
JOHNSON, MR ;
LEIGH, SJ ;
SPENCER, N ;
SUTHERLAND, IO ;
NEWTON, RF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (09) :2193-2202
[18]   LI-7, NA-23, AND CS-133 NMR AND FAR IR STUDY OF ALKALI COMPLEXES WITH C222-DILACTAM IN VARIOUS SOLVENTS [J].
HOURDAKIS, A ;
POPOV, AI .
JOURNAL OF SOLUTION CHEMISTRY, 1977, 6 (05) :299-307
[19]   A BINARY QUINONE RECEPTOR [J].
HUNTER, CA ;
PURVIS, DH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (06) :792-795
[20]   THERMODYNAMIC AND KINETIC DATA FOR MACROCYCLE INTERACTION WITH NEUTRAL MOLECULES [J].
IZATT, RM ;
BRADSHAW, JS ;
PAWLAK, K ;
BRUENING, RL ;
TARBET, BJ .
CHEMICAL REVIEWS, 1992, 92 (06) :1261-1354