PREPARATION OF 9-ARYL (OR HETEROARYL)METHYLIDENE-10-(METHOXYIMINO)-PHENANTHRENES AND THEIR THERMAL ELECTROCYCLIZATION TO FUSED QUINOLINES

被引:16
作者
NICOLAIDES, DN
LITINAS, KE
PAPAGEORGIOU, GK
STEPHANIDOUSTEPHANATOU, J
机构
[1] Laboratory of Organic Chemistry, University of Thessaloniki, Thessaloniki
关键词
D O I
10.1002/jhet.5570280125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
o-Quinone methanide N-methoxyimines 6a-c, 7a-c, 11a-b and 12a, easily prepared from the reaction of 10-(methoxyimino)phenanthrene-9-one (3) with phosphonium salts 5a-c, 10a-b in the presence of lithium hydroxide, are thermally converted into dibenzo[f,h]quinolino[2,3-x]fused compounds 9a-c and 13a-b, in high yield.
引用
收藏
页码:139 / 143
页数:5
相关论文
共 20 条
[1]   CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS .3. ALKALINE-HYDROLYSIS OF HETEROARYLMETHYL ANALOGS OF BENZYLTRIPHENYLPHOSPHONIUM BROMIDE - RELATIVE STABILITIES OF HETEROARYLMETHYL CARBANIONS [J].
ALLEN, DW ;
HUTLEY, BG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (01) :67-&
[2]   A GENERAL AND PRACTICABLE SYNTHESIS OF POLYCYCLIC HETEROAROMATIC-COMPOUNDS .3. EXTENSION OF THE SYNTHESIS TO QUINONE METHIDES OF NAPHTHALENE, PHENANTHRENE, AND BENZENE [J].
BILGIC, O ;
YOUNG, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (06) :1233-1239
[3]   GENERATION AND REACTIONS OF AZAXYLYLENES [J].
BOWEN, RD ;
DAVIES, DE ;
FISHWICK, CWG ;
GLASBEY, TO ;
NOYCE, SJ ;
STORR, RC .
TETRAHEDRON LETTERS, 1982, 23 (43) :4501-4504
[4]   N-PHENYLBENZOAZETINE [J].
BURGESS, EM ;
MCCULLAGH, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (07) :1580-+
[5]   ORTHOQUINODIMETHANES [J].
CHARLTON, JL ;
ALAUDDIN, MM .
TETRAHEDRON, 1987, 43 (13) :2873-2889
[6]   NOVEL PHOTOCHEMICAL AND THERMAL ELECTROCYCLIZATION TO FUSED QUINOLINES [J].
ELFERINK, VHM ;
BOS, HJT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (13) :882-883
[7]  
ELIX JA, 1970, J AM CHEM SOC, V94, P973
[8]  
Fishwick C. W. W., 1988, CHEM QUINONOID COMPO, V2, P403
[9]   THE REACTION OF BENZYNE WITH IMINES [J].
FISHWICK, CWG ;
GUPTA, RC ;
STORR, RC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12) :2827-2829
[10]   A SIMPLE ROUTE TO C-FUNCTIONALIZED AZAXYLYLENES AND DIAZAXYLYLENES [J].
FISHWICK, CWG ;
STORR, RC ;
MANLEY, PW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) :1304-1305