aza-annulation of tetrahydroisoquinoline derived enamines:: Efficient and convergent routes to novel functionalized benzo[a]quinolizin-4-ones and pyrimido[6,1-a]isoquinoline derivatives

被引：18
作者：
Chakrabarti, S
Srivastava, MC
Ila, H [1 ]
Junjappa, H
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
[2] BioOrgan & Appl Mat Pvt Ltd, Bangalore 560058, Karnataka, India
来源：
SYNLETT | 2003年 / 15期
关键词：
aza-annulations; enamines; 1,3-biselectrophiles; benzo[alquinolizin-4-ones; pyrimido[6,1-a]isoquinolines;
D O I：
10.1055/s-2003-42120
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 1,2,3,4-tetrahydroisoquinoline derived push-pull enaminones and nitroenamine have been investigated in aza-annulation reactions with various 1,3-biselectrophiles leading to the synthesis of novel functionalized benzo[a]quinolizin-4-ones and pyrimido[6,1-a]isoquinoline derivatives.
引用
收藏
页码：2369 / 2373
页数：5
相关论文
共 34 条
[1]   Ring annulation with tetrahydroisoquinoline-derived enaminones:: Highly convergent routes to functionalized pyrrolo[2,1-a]- and indolo[2,1-a]isoquinolines [J].
Barun, O ;
Chakrabarti, S ;
Ila, H ;
Junjappa, H .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4457-4461
[2]  
Barun O, 2000, SYNLETT, P653
[3]   Aza-annulation as a versatile approach to the synthesis of non-benzodiazepene compounds for the treatment of sleep disorders [J].
Benovsky, P ;
Stille, JR .
TETRAHEDRON LETTERS, 1997, 38 (49) :8475-8478
[4]   STUDIES ON THE SYNTHESIS OF THE BENZO[A]QUINOLIZIDIN-2-ONE RING-SYSTEM - PREPARATION OF A 1,1-DIMETHYL DERIVATIVE [J].
BOSCH, J ;
DOMINGO, A ;
LINARES, A .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1075-1080
[5]   SYNTHESEVERSUCHE IN DER EMETIN-REIHE .3. 2-HYDROXY-HYDROBENZO[A]CHINOLIZINE [J].
BROSSI, A ;
CHOPARDDITJEAN, LH ;
SCHNIDER, O .
HELVETICA CHIMICA ACTA, 1958, 41 (06) :1793-1806
[6]   SYNTHESEVERSUCHE IN DER EMETINREIHE RAC EMETIN-ISOMERE DER 2,3-CIS-REIHE [J].
BROSSI, A ;
SCHNIDER, O .
HELVETICA CHIMICA ACTA, 1962, 45 (06) :1899-&
[7]   SYNTHESIS AND AMOEBICID PROPERTIES OF EMETIN ANALOGS - ANALYSIS OF NEW COMPOUNDS BY C-13-NMR .1. B-C CIS-FUSED OR TRANS-FUSED (+/-) 1-ALKYL-3-DESETHYL-EMETIN [J].
BUZAS, A ;
CAVIER, R ;
COSSAIS, F ;
FINET, JP ;
JACQUET, JP ;
LAVIELLE, G ;
PLATZER, N .
HELVETICA CHIMICA ACTA, 1977, 60 (07) :2122-2134
[8]   SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF A SERIES OF SPIRO[1,3,4,6,7,11B-HEXAHYDRO-2H-BENZO[A]QUINOLIZINE-2,5'-OXAZOLIDIN-2'-ONE]S [J].
CAROON, JM ;
CLARK, RD ;
KLUGE, AF ;
LEE, CH ;
STROSBERG, AM .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (10) :1426-1433
[9]   TRICYCLIC PYRIDINE-DERIVATIVES WITH HIGH-AFFINITY TO THE CENTRAL BENZODIAZEPINE RECEPTOR [J].
FISCHER, U ;
MOHLER, H ;
SCHNEIDER, F ;
WIDMER, U .
HELVETICA CHIMICA ACTA, 1990, 73 (04) :763-781
[10]  
Helmuth R., 1967, ALKALOIDS CHEMISTRY, V9, P41
1234