Synthesis of oxacalixarenes incorporating nitrogen heterocycles: Evidence for thermodynamic control

被引:83
作者
Katz, Jeffrey L. [1 ]
Geller, Bram J. [1 ]
Conry, Rebecca R. [1 ]
机构
[1] Colby Coll, Dept Chem, Waterville, ME 04901 USA
关键词
D O I
10.1021/ol060823e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxacalix[2]arene[2] hetarenes are formed in a single step by cyclooligomerization of meta-diphenols with meta-dichlorinated azaheterocycles. The high selectivity for cyclic tetramer formation results from thermodynamic product control. Macrocycles as large as oxacalix[5] arene[5]hetarenes have been isolated under nonequilibrating conditions.
引用
收藏
页码:2755 / 2758
页数:4
相关论文
共 42 条
[1]   CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES [J].
BOHMER, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :713-745
[2]   SYNTHESIS AND CHARACTERIZATION OF OXYGEN AND SULFUR BRIDGED AROMATIC MACROCYCLES [J].
BOTTINO, F ;
FOTI, S ;
PAPPALARDO, S .
TETRAHEDRON, 1976, 32 (21) :2567-2570
[3]  
Casnati A, 2001, CALIXARENES 2001, P365
[4]   Polyhalogenated heterocyclic compounds. part 50. Macrocycles from perfluoro-4-isopropylpyridine [J].
Chambers, RD ;
Hoskin, PR ;
Kenwright, AR ;
Khalil, A ;
Richmond, P ;
Sandford, G ;
Yufit, DS ;
Howard, JAK .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (12) :2137-2147
[5]  
DHAWAN B, 1987, MAKROMOL CHEM, V188, P921
[6]  
Freund T, 1998, EUR J ORG CHEM, V1998, P555
[7]   Azacalix[n]arenes with -NH- amino group:: NH•••OCH3 interaction-assisted synthesis, structure, and reactivity [J].
Fukushima, W ;
Kanbara, T ;
Yamamoto, T .
SYNLETT, 2005, (19) :2931-2934
[8]   SUBSTITUTED MACROCYCLIC ARYL TETRAETHERS [J].
GILBERT, EE .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (06) :899-904
[9]   Design, synthesis, computational prediction, and biological evaluation of ester soft drugs as inhibitors of dihydrofolate reductase from Pneumocystis carinii [J].
Graffner-Nordberg, M ;
Kolmodin, K ;
Åqvist, J ;
Queener, SF ;
Hallberg, A .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (15) :2391-2402
[10]  
GUNTHER L, 1973, Patent No. 2206506