DIRECTABLE REGIOCHEMISTRY IN NAPHTHAZARINS VIA THE USE OF MASKED DERIVATIVES

被引:11
作者
BLOOMER, JL [1 ]
STAGLIANO, KW [1 ]
机构
[1] TEMPLE UNIV,DEPT CHEM,PHILADELPHIA,PA 19122
关键词
D O I
10.1016/0040-4039(93)89004-A
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The carboethoxynaphthol 3d was converted via salcomine oxidation to the masked carboethoxynaphthazarin 4b which could undergo nucleophilic addition or, if unmasked, transfer quinone reactivity to the alternative ring in form 5. The latter should undergo regiospecific Diels-Alder reactions.
引用
收藏
页码:757 / 760
页数:4
相关论文
共 17 条
[1]  
ARORA PC, 1974, CAN J CHEM, V52, P67
[2]   AN EFFICIENT ROUTE TO 3-CHLOROJUGLONES [J].
BLOOMER, JL ;
GAZZILLO, JA .
TETRAHEDRON LETTERS, 1989, 30 (10) :1201-1204
[3]   REGIOSPECIFIC SYNTHESIS OF QUINIZARIN AND NAPHTHAZARIN DERIVATIVES BY CYCLOADDITION [J].
CAMERON, DW ;
FEUTRILL, GI ;
MCKAY, PG .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (10) :2095-2109
[4]   NUCLEOPHILIC ALKENES .5. FORMATION OF A NAPHTHALENIC SYSTEM BY ADDITION OF 1,1-DIMETHOXYETHENE TO 2-ACETYL-1,4-BENZOQUINONE AND SUBSEQUENT TRANSFORMATION [J].
CAMERON, DW ;
FEUTRILL, GI ;
SEFTON, MA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (09) :2099-2101
[5]   POLYCYCLIC HYDROXYQUINONES .19. REGIOSPECIFIC SYNTHESIS OF ANTHRACYCLINONES VIA THE DIELS-ALDER REACTION WITH DICHLORONAPHTHAZARINS [J].
ECHAVARREN, A ;
PRADOS, P ;
FARINA, F .
TETRAHEDRON, 1984, 40 (22) :4561-4567
[6]   WELKSTOFFE UND ANTIBIOTIKA - SYNTHESE VON JAVA']JAVANICIN-5,8-DIMETHYLATHER UND KONSTITUTION VON JAVA']JAVANICIN UND FUSARUBIN [J].
HARDEGGER, E ;
PFIFFNER, A ;
STEINER, K ;
WIDMER, E .
HELVETICA CHIMICA ACTA, 1964, 47 (07) :2027-&
[7]   FRIEDEL-CRAFTS CONDENSATIONS WITH MALEIC ANHYDRIDES .3. SYNTHESIS OF POLYHYDROXYLATED NAPHTHOQUINONES [J].
HUOT, R ;
BRASSARD, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (05) :838-842
[8]   SYNTHESIS AND STEREOCHEMISTRY OF (E,E)-1,4-DIACETOXY-2-METHYL-1,3-BUTADIENE AND RELATED COMPOUNDS [J].
KEANA, JFW ;
ECKLER, PE .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (15) :2625-2627
[9]  
KELLY TR, 1984, TETRAHEDRON, V40, P4569
[10]  
LLATSCH H, 1986, LIEBIGS ANN CHEM, V10, P1655