SYNTHESIS AND PHOTOOXYGENATION OF 2,3,6-TRIMETHYLFURO[2,3-B][1]NAPHTHO]4A,7A-E,F]PYRIDA-5,7-DIONE, A POTENTIAL CHEMILUMINESCENT PROBE FOR SINGLET OXYGEN

被引：31

作者：

ADAM, W

QIAN, XH

SAHAMOLLER, CR

机构：

[1] Institute of Organic Chemistry, University of Würzburg, D-8700 Würzburg, Am Hubland

来源：

TETRAHEDRON | 1993年 / 49卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(01)80310-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As potential chemiluminescent probe for singlet oxygen, the furonaphthalimide 4 was synthesized in five steps (ca. 25% overall yield), by starting from commercially available 4-chloro-1,8-naphthalic anhydride, its photooxygenation at -10-degrees-C gave the cleavage product 6 of the intermediary dioxetane 5. which is thermally too labile for isolation and could not be detected even by low temperature NMR spectroscopy. The new 1,8-naphthalimide derivatives 3, 4 and 6 were fully characterized and their absorption and fluorescence spectral properties were determined.

引用

收藏

页码：417 / 422

页数：6

相关论文

共 11 条

[1] PHOTOBIOLOGICAL STUDIES WITH DIOXETANES IN ISOLATED DNA, BACTERIA, AND MAMMALIAN-CELLS [J].

ADAM, W ;

BEINHAUER, A ;

MOSANDL, T ;

SAHAMOLLER, C ;

VARGAS, F ;

EPE, B ;

MULLER, E ;

SCHIFFMANN, D ;

WILD, D .

ENVIRONMENTAL HEALTH PERSPECTIVES, 1990, 88 :89-97

[2] NUCLEAR SUBSTITUTION BY ANIONS AND SELF-UNION IN 1-8-NAPHTHALIMIDE AND ITS N-METHYL DERIVATIVE [J].

BRADLEY, W ;

PEXTON, FW .

JOURNAL OF THE CHEMICAL SOCIETY, 1954, (DEC) :4432-4435

[3] HETEROCYCLIC DERIVATIVES OF NAPHTHALENE-1,8-DICARBOXYLIC ANHYDRIDE .3. BENZO[K,L]THIOXANTHENE-3,4-DICARBOXIMIDES [J].

GRAYSHAN, PH ;

KADHIM, AM ;

PETERS, AT .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (01) :33-38

[4]

Lamola A, 1984, PURE APPL CHEM, V56, P939

[5] PREPARATION OF 1,8-NAPHTHALIMIDES AS CANDIDATE FLUORESCENT-PROBES OF HYPOXIC CELLS [J].

MIDDLETON, RW ;

PARRICK, J .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (06) :1567-1572

[6] SYNTHESIS AND FLUORESCENCE OF N-SUBSTITUTED-1,8-NAPHTHALIMIDES [J].

MIDDLETON, RW ;

PARRICK, J ;

CLARKE, ED ;

WARDMAN, P .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (03) :849-855

[7] SYNTHESIS AND PHOTOPHYSICAL PROPERTIES OF SOME N-SUBSTITUTED-1,8-NAPHTHALIMIDES [J].

PARDO, A ;

MARTIN, E ;

POYATO, JML ;

CAMACHO, JJ ;

BRANA, MF ;

CASTELLANO, JM .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1987, 41 (01) :69-78

[8]

PARDO A, 1986, J PHOTOCHEM, V36, P323

[9]

QIAN XH, 1989, DYES PIGMENTS, V11, P13

[10] PHOTOELECTRIC SENSITIZING EFFECTS OF 1,8-NAPHTHALIMIDES AND 7H-BENZIMIDAZO[2,1-A]BENZ[D,E]ISOQUINOLIN-7-ONES DERIVATIVES ON ZNO [J].

QIAN, XH ;

ZHU, ZH ;

CHEN, KC ;

YIN, QJ ;

ZHU, GG .

MATERIALS CHEMISTRY AND PHYSICS, 1989, 23 (03) :335-339