New synthetic routes to molrac spacer and platform systems which incorporate the 1,4-benzoquinone chromophore

被引:13
作者
Butler, DN [1 ]
Smits, R [1 ]
Evans, DAC [1 ]
Weerasuria, KDV [1 ]
Warrener, RN [1 ]
机构
[1] UNIV CENT QUEENSLAND, CTR MOL ARCHITECTURE, ROCKHAMPTON, QLD 4702, AUSTRALIA
基金
澳大利亚研究理事会;
关键词
D O I
10.1016/0040-4039(96)00219-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cycloaddition routes are described for the preparation of rigid molrac olefins containing an inbuilt 1,4-benzoquinone chromophore using either a divergent approach as used in the synthesis of platform molrac 1 and its geometrical isomer 2, or a serial approach used to prepare 20. A short route to bismethanoanthraquinones 3 and 7 is also reported.
引用
收藏
页码:2157 / 2160
页数:4
相关论文
共 22 条
[1]   CAVITY-SHAPED MOLRACS WITH INWARD-FACING, DIRECT LINE-OF-SIGHT FUNCTIONALITY [J].
BUTLER, DN ;
TEPPERMAN, PM ;
GAU, RA ;
WARRENER, RN ;
WATSON, WH ;
KASHYAP, RP .
TETRAHEDRON LETTERS, 1995, 36 (34) :6145-6148
[2]   PHOTOCHEMICAL CYCLISATION OF DIELS-ALDER ADDUCTS [J].
COOKSON, RC ;
CRUNDWELL, E ;
HILL, RR ;
HUDEC, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (SEP) :3062-&
[3]  
COOKSON RC, 1985, J CHEM IND LONDON, P1003
[4]   SYNTHESES OF RIGID AND SEMIRIGID MOLECULES FOR INVESTIGATIONS OF PHOTOINDUCED ELECTRON-TRANSFER REACTIONS [J].
KUMAR, K ;
TEPPER, RJ ;
ZENG, Y ;
ZIMMT, MB .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4051-4066
[5]   SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF A NOVEL PAIR OF RIGID DIASTEREOMERIC TRIADS [J].
LAWSON, JM ;
CRAIG, DC ;
OLIVER, AM ;
PADDONROW, MN .
TETRAHEDRON, 1995, 51 (13) :3841-3864
[6]  
MITSUDO T, 1994, ANGEW CHEM INT EDIT, V33, P580, DOI 10.1002/anie.199405801
[7]   RUTHENIUM-CATALYZED [2+2] CROSS-ADDITION OF NORBORNENE DERIVATIVES AND DIMETHYL ACETYLENEDICARBOXYLATE [J].
MITSUDO, T ;
KOKURYO, K ;
SHINSUGI, T ;
NAKAGAWA, Y ;
WATANABE, Y ;
TAKEGAMI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25) :4492-4495
[8]   HIGHER-ORDER CYCLOADDITION REACTIONS OF ADAMANTYL ISOBENZOFULVENE AND ISOBENZOFURAN - A MICROSCALE SYNTHESIS ILLUSTRATING THE INVOLVEMENT OF HIGHLY REACTIVE INTERMEDIATES AND A SIMPLE FMO TREATMENT OF THEIR CYCLOADDITION PERISELECTIVITIES [J].
RUSSELL, RA ;
LONGMORE, RW ;
WARRENER, RN .
JOURNAL OF CHEMICAL EDUCATION, 1992, 69 (02) :164-168
[9]   THE USE OF PEPTIDIC FRAMEWORKS FOR THE CONSTRUCTION OF MOLECULAR RECEPTORS AND DEVICES [J].
VOYER, N ;
LAMOTHE, J .
TETRAHEDRON, 1995, 51 (34) :9241-9284
[10]   THE SYNTHESIS OF SPACER MOLECULES CONTAINING AN ALCOHOL GROUP AT EACH TERMINUS [J].
WARRENER, RN ;
GROUNDWATER, P ;
PITT, IG ;
BUTLER, DN ;
RUSSELL, RA .
TETRAHEDRON LETTERS, 1991, 32 (16) :1885-1888