ARYL-ARYL COUPLING INDUCED BY NORMAL-TRIBUTYLSTANNYL HYDRIDE AN EFFICIENT PHENANTHRIDINE SYNTHESIS

被引:37
作者
ROSA, AM
PRABHAKAR, S
LOBO, AM
机构
[1] UNIV NOVA LISBOA, FCT, DEPT QUIM, SECCAO QUIM ORGAN APLICADA, P-2825 MONTE DE CAPARICA, PORTUGAL
[2] INIC, CTR QUIM ESTRUTURAL, P-1096 LISBON, PORTUGAL
关键词
D O I
10.1016/S0040-4039(00)98810-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-(o-Bromobenzyl) anilines undergo smooth cyclisation,via dihydrophenanthridines, to phenanthridines by intramolecular addition of aryl radicals to theoposition of the aryl ring bearing the nitrogen atom. © 1990 Pergamon Press plc.
引用
收藏
页码:1881 / 1884
页数:4
相关论文
共 10 条
[1]  
BENNINGTON F, 1958, J ORG CHEM, V23, P19
[2]   REDUCTION OF SCHIFF BASES WITH SODIUM BOROHYDRIDE [J].
BILLMAN, JH ;
DIESING, AC .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (09) :1068-1070
[3]   SYNTHESIS OF OXINDOLES BY RADICAL CYCLIZATION [J].
BOWMAN, WR ;
HEANEY, H ;
JORDAN, BM .
TETRAHEDRON LETTERS, 1988, 29 (50) :6657-6660
[4]   INTRAMOLECULAR RADICAL CYCLIZATION REACTIONS - AN APPROACH TO THE INDOLE ALKALOIDS [J].
DITTAMI, JP ;
RAMANATHAN, H .
TETRAHEDRON LETTERS, 1988, 29 (01) :45-48
[5]  
PAULSEN H, 1983, LIEBIGS ANN CHEM, P535
[6]   BORON COMPLEXES AS CONTROL SYNTHONS IN PHOTOCYCLIZATIONS - IMPROVED PHENANTHRIDINE SYNTHESIS [J].
PRABHAKAR, S ;
LOBO, AM ;
TAVARES, MR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (20) :884-885
[7]   SYNTHETIC CONNECTIONS TO THE AROMATIC DIRECTED METALATION REACTION - RADICAL-INDUCED CYCLIZATION TO SUBSTITUTED BENZOFURANS, BENZOPYRANS, AND FUROPYRIDINES [J].
SHANKARAN, K ;
SLOAN, CP ;
SNIECKUS, V .
TETRAHEDRON LETTERS, 1985, 26 (49) :6001-6004
[8]   THE DIRECTED METALATION CONNECTION TO ARYL ARYL CROSS COUPLING - REGIOSPECIFIC SYNTHESIS OF PHENANTHRIDINES, PHENANTHRIDINONES AND THE BIPHENYL ALKALOID ISMINE [J].
SIDDIQUI, MA ;
SNIECKUS, V .
TETRAHEDRON LETTERS, 1988, 29 (43) :5463-5466
[9]   A GENERAL-SYNTHESIS OF 5-ARYLNICOTINATES [J].
THOMPSON, WJ ;
GAUDINO, J .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5237-5243
[10]   A RADICAL CYCLIZATION BETWEEN ENOL SILYL ETHERS AND ARYL OR ALKENYL BROMIDE MOIETIES [J].
URABE, H ;
KUWAJIMA, I .
TETRAHEDRON LETTERS, 1986, 27 (12) :1355-1358