PREPARATION AND THERMAL RING-CLOSURE OF BETA-ARYL VINYL CARBODI-IMIDES - SYNTHESIS OF ISOQUINOLINE DERIVATIVES

被引：43
作者：
MOLINA, P
TARRAGA, A
LIDON, MJ
机构：
[1] Departamento de Química Orgánica, Universidad de Murcia, Campus de Espinardo
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 06期
关键词：
D O I：
10.1039/p19900001727
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of the iminophosphoranes (7)-(9), derived from α-azidocinnamates and triphenylphosphine, with aromatic isocyanates gives either 1-arylaminoisoquinoline-3-carboxylates (10)-(12) or the corresponding carbodi-imides (14)-(18) which by thermal treatment at 230°C are converted into 1-(N-aryl-N-imidazolylamino)isoquinoline-3-carboxylates (19)-(20). The iminophosphoranes (7) and (8) also react with aroyl chlorides to give the oxazolone derivatives (23)-(26).
引用
收藏
页码：1727 / 1731
页数：5
相关论文
共 18 条
[1]  
ARDABILCHI N, 1977, TETRAHEDRON LETT, P4107
[2]  
CROASMAN WR, 1987, 2 DIMENSIONAL NMR SP
[3]  
DUTTA NL, 1971, J INDIAN CHEM SOC, V48, P873
[4]  
GENSLER WJ, 1951, ORG REACTIONS, V6, P191
[5]  
GOSZCZYNSKI S, 1970, ROCZN CHEM, V44, P109
[6]   FORMATION OF INDOLES, ISOQUINOLINES, AND OTHER FUSED PYRIDINES FROM AZIDOACRYLATES [J].
HENN, L ;
HICKEY, DMB ;
MOODY, CJ ;
REES, CW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (09) :2189-2196
[7]   SYNTHESIS OF ISOQUINOLINES FROM AZIDOCINNAMATES - THE EFFECT OF IODINE [J].
HICKEY, DMB ;
MOODY, CJ ;
REES, CW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (01) :3-4
[8]  
JONES G, 1984, COMPREHENSIVE HETERO, V2, P412
[9]   NEW HETEROCYCLIZATION REACTIONS FOR THE PREPARATION OF FUSED [1,2,4]TRIAZOLES - SYNTHESIS OF 1,2,4-TRIAZOLO[4,3-B][1,2,4]TRIAZOLE DERIVATIVES FROM 4-AMINO-1,2,4-TRIAZOLES AND CARBODI-IMIDES OR VIA IMINOPHOSPHORANES AND DISUBSTITUTED THIOUREAS [J].
MOLINA, P ;
ALAJARIN, M ;
FERAO, A ;
DEVEGA, MJP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2667-2672
[10]   CARBODIIMIDE-MEDIATED ANNELATION OF A [1,2,4]TRIAZOLE RING INTO A HETEROCYCLIC RING - SYNTHESIS OF [1,2,4]TRIAZOLO[4,3-B]-TRIAZOLE, IMIDAZO[1,2-B] [1,2,4]TRIAZOLE AND [1,2,4]TRIAZOLO-[1,5-D] [1,2,4]TRIAZINE DERIVATIVES [J].
MOLINA, P ;
ALAJARIN, M ;
FERAO, A ;
LORENZO, A ;
VILAPLANA, MJ ;
ALLER, E ;
PLANES, J .
HETEROCYCLES, 1988, 27 (01) :161-171
12