REACTIVITY AND SYNTHETIC APPLICATIONS OF BIS(IMINOPHOSPHORANES) - ONE-POT PREPARATION OF PYRIDO[2,3,4-DE]QUINAZOLINES AND BENZO[DE][1,6]NAPHTHYRIDINES

被引:42
作者
MOLINA, P
ALJARIN, M
VIDAL, A
机构
[1] Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, E-30071, Murcia
关键词
D O I
10.1021/jo00051a007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aza-Wittig reaction of bis(iminophosphorane) 4 with 2 equiv of isocyanate leads directly to pyrido[2,3,4-de]quinazolines 5. Iminophosphoranes 8, available from 4 and 1 equiv of the appropriate isocyanate, react either with 1 equiv of isocyanate or ketene to give pyrido[2,3,4-de]quinazolines 9 or benzo[de][1,6]naphthyridines 10, respectively. Bis(iminophosphorane) 4 by sequential treatment with aldehydes and isocyanates yielded 2,3-dihydropyrido[2,3,4-de]quinazolines 17.
引用
收藏
页码:6703 / 6711
页数:9
相关论文
共 20 条
[1]   SYNTHESIS OF REACTIVITY OF LAMBDA-5-PHOSPHAZENES - USES AS SYNTHETIC INTERMEDIATES [J].
BARLUENGA, J ;
PALACIOS, F .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (01) :1-65
[2]  
BODEKER J, 1979, Z CHEM, V19, P59
[3]   REACTIONS OF ORTHO-PHENYLENEDIAMINE AND SOME IMINOPHOSPHORANE DERIVATIVES WITH DIMETHYL ACETYLENEDICARBOXYLATE [J].
BRIGGS, EM ;
BROWN, GW ;
DAWSON, WT ;
JIRICNY, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (15) :641-642
[4]   CALCULATION OF SOME C-13 CHEMICAL-SHIFTS FOR COMPOUNDS CONTAINING CUMULATIVE DOUBLE-BONDS - ALLENE, KETENIMINE AND CARBODIIMIDE SERIES [J].
COLLIER, C ;
WEBB, GA .
ORGANIC MAGNETIC RESONANCE, 1979, 12 (11) :659-660
[5]   THE AZA-WITTIG REACTION IN HETEROCYCLIC SYNTHESIS - A REVIEW [J].
EGUCHI, S ;
MATSUSHITA, Y ;
YAMASHITA, K .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1992, 24 (02) :209-&
[6]   C-13-NMR SPECTRA AND BONDING SITUATION IN KETENIMINES [J].
FIRL, J ;
RUNGE, W ;
HARTMANN, W ;
UTIKAL, HP .
CHEMISTRY LETTERS, 1975, (01) :51-54
[7]   RECENT ADVANCES IN THE STAUDINGER REACTION [J].
GOLOLOBOV, YG ;
KASUKHIN, LF .
TETRAHEDRON, 1992, 48 (08) :1353-1406
[8]  
Gusar N. I., 1991, RUSS CHEM REV, V60, P146
[9]  
HUISGEN R, 1969, J CHEM BER, V102, P1948
[10]  
KATRITZKY AR, 1990, J CHEM RES-S, P330