The stereochemistry of organometallic compounds .42. The preparation of [2,1-b]quinazolines involving rhodium-catalysed hydroformylation of 2-amino-N-alkenylbenzylamines

被引:30
作者
Campi, EM
Habsuda, J
Jackson, WR
Jonasson, CAM
McCubbin, QJ
机构
[1] Department of Chemistry, Monash University, Clayton
关键词
D O I
10.1071/CH9952023
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rhodium-catalysed reactions of 2-amino-N-alkenylbenzylamines with H-2/CO give hexahydropyrrolo- and hexahydropyrido-[2,1-b]quinazolines. Reactions of N-allyl derivatives give a single regioisomer, and reactions of but-3-enyl analogues give mixtures of pyrrolo and pyrido derivatives. Some reactions give significant amounts (10-30%) of tetrahydro derivatives. The origin of these compounds remains unclear.
引用
收藏
页码:2023 / 2033
页数:11
相关论文
共 22 条
[1]  
ALBINI A, 1988, HETEROCYCLES, V27, P1207
[2]   THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .35. HYDROFORMYLATION OF ORTHO-PROPENYLANILINES AND ORTHO-PROPENYLPHENOLS - A NEW ROUTE TO 4,5-DIHYDRO-3H-1-BENZAZEPINES [J].
ANASTASIOU, D ;
JACKSON, WR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (01) :21-37
[3]   STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .39. SYNTHESIS OF BENZIMIDAZOLES CONTAINING A FUSED ALICYCLIC RING BY RHODIUM - CATALYZED HYDROFORMYLATION OF N-ALKENYL-1,2-DIAMINOBENZENES [J].
ANASTASIOU, D ;
CAMPI, EM ;
CHAOUK, H ;
JACKSON, WR .
TETRAHEDRON, 1992, 48 (36) :7467-7478
[4]  
BEHR LC, 1967, CHEM HETEROCYCLIC CO, P289
[5]   THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .61. THE PREPARATION OF QUINAZOLINES AND QUINAZOLINONES INVOLVING RHODIUM-CATALYZED HYDROFORMYLATION OF ALKENYL ANILINES [J].
CAMPI, EM ;
JACKSON, WR ;
MCCUBBIN, QJ ;
TRNACEK, AE .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (06) :1061-1070
[6]  
ELGUERO J, 1969, B SOC CHIM FR, P2064
[7]   6,7,8,9-TETRAHYDROPYRIDOQUINAZOLINES A NEW CLASS OF ALKALOIDS FROM MACKINLAYA SPECIES (ARALIACEAE) [J].
FITZGERALD, JS ;
JOHNS, SR ;
LAMBERTON, JA ;
REDCLIFFE, AH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1966, 19 (01) :151-+
[8]   IDENTIFICATION OF A MINOR ALKALOID OF MACKINLAYA-MACROSCIADIA (ARALIACEAE) AS DEOXYVASICINONE [J].
HART, NK ;
JOHNS, SR ;
LAMBERTON, JA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (01) :223-+
[9]   3,4,5,6,7,8-HEXAHYDRO-1,7-BENZODIAZECIN-2(1H)-ONE FROM EXTRACTS OF MACKINLAYA SPECIES [J].
JOHNS, SR ;
LAMBERTON, JA ;
SUARES, H .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (06) :1007-1008
[10]  
KORETSKAYA NI, 1958, ZH OBSHCH KHIM+, V28, P1087