SYNTHESIS OF AZA-BRIDGED CALIX(4-METHOXY)TRIAZINES TOWARD FLATTENED π-CONJUGATED MACROCYCLES

Calixtriazines containing a 4-alkoxy-l,3,5-triazine backbone were efficiently synthesized by sequential fragment coupling started from 4-alkoxy-2,6-dichrolo-l,3,5-triazine. These macrocycles tend to form flattened conformations, leading to a stable π-conjugated system, presumably due to the electronic features of the alkoxy-substituent on the triazine rings.

[1]  De‐Xian Wang,et al.  En route to inherently chiral tetraoxacalix[2]arene[2]triazines , 2007 .

[2]  De‐Xian Wang,et al.  Formation and conformational conversion of flattened partial cone oxygen bridged calix[2]arene[2]triazines. , 2007, Organic letters.

[3]  Chun Zhang,et al.  Triptycene-based expanded oxacalixarenes: synthesis, structure, and tubular assemblies in the solid state. , 2007, The Journal of organic chemistry.

[4]  De‐Xian Wang,et al.  Efficient functionalizations of heteroatom-bridged calix[2]arene[2]triazines on the larger rim. , 2007, The Journal of organic chemistry.

[5]  De‐Xian Wang,et al.  Synthesis of tetraazacalix[2]arene[2]triazines: tuning the cavity by the substituents on the bridging nitrogen atoms. , 2006, Organic letters.

[6]  G. Błotny Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis , 2006 .

[7]  Hai‐Bo Yang,et al.  A general and high yielding fragment coupling synthesis of heteroatom-bridged calixarenes and the unprecedented examples of calixarene cavity fine-tuned by bridging heteroatoms. , 2004, Journal of the American Chemical Society.

[8]  Xiaoping Yang,et al.  Synthesis of novel rigid triazine-based calix[6]arenes , 2003 .

[9]  J. Reedijk,et al.  New polydentate and polynucleating N-donor ligands from amines and 2,4,6-trichloro-1,3,5-triazine , 2002 .

[10]  V. Paraschiv,et al.  Nanostructures via noncovalent synthesis: 144 hydrogen bonds bring together 27 components. , 2001, The Journal of organic chemistry.

[11]  C. Lowe,et al.  Synthesis of Macrocyclic, Triazine‐Based Receptor Molecules , 2001 .

[12]  Kumar Biradha,et al.  Molecular paneling via coordination , 2001 .

[13]  C. Lowe,et al.  A stepwise synthesis of triazine-based macrocyclic scaffolds , 2000 .

[14]  K. Terao,et al.  Synthesis and characterization of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride , 1999 .

[15]  B. Costisella,et al.  Synthese und Transportuntersuchungen von Dioxapolyazacalix[4]arenen und Triazino‐Kronenethern , 1998 .

[16]  Philip A. Gale,et al.  Calix[4]pyridine: a new arrival in the heterocalixarene family , 1998 .

[17]  A. Blake,et al.  Synthesis and Structural Characterization of an S-linked Calix[3]azine , 1997 .

[18]  Atsushi Ikeda,et al.  Novel Cavity Design Using Calix[n]arene Skeletons: Toward Molecular Recognition and Metal Binding. , 1997, Chemical reviews.

[19]  Kazuaki Ito,et al.  Synthesis and properties of sulfur-bridged analogs of p-tert-Butylcalix[4]arene☆ , 1997 .

[20]  Philip A. Gale,et al.  Calix[4]pyrroles:  Old Yet New Anion-Binding Agents , 1996 .

[21]  D. Craig,et al.  Synthesis and crystal structure of a calix[3]indole with cone conformation: A new molecular receptor , 1996 .

[22]  V. Böhmer Calixarenes, Macrocycles with (Almost) Unlimited Possibilities , 1995 .

[23]  S. Shinkai,et al.  Recent Topics on Functionalization and Recognition Ability of Calixarenes: The ‘Third Host Molecule’ , 1995 .

[24]  G. Lutze,et al.  Neue Azacyclophane aus Cyanurchlorid und Diaminen , 1995 .

[25]  A. Whiting,et al.  SYNTHESIS OF CALIXFURAN MACROCYCLES AND EVIDENCE FOR GAS-PHASE AMMONIUM ION COMPLEXATION , 1994 .

[26]  S. Shinkai Calixarenes - the third generation of supramolecules , 1993 .

[27]  K. Yoshimura,et al.  The first synthesis and properties of hexahomotriazacalix[3]arene , 1992 .

[28]  B. Dhawan,et al.  CALIXARENES. 10. OXACALIXARENES , 1983 .

[29]  G. Ehlers,et al.  s-Triazines. II. The synthesis of some new cyclopoly-s-triazinylene thioethers and disulfides , 1966 .