SYNTHESIS AND CYCLOADDITION OF 2,4-DIHYDROPYRROLO[3,4-B]INDOLES

被引:19
作者
JEEVANANDAM, A [1 ]
SRINIVASAN, PC [1 ]
机构
[1] UNIV MADRAS,DEPT ORGAN CHEM,MADRAS 600025,TAMIL NADU,INDIA
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 20期
关键词
D O I
10.1039/p19950002663
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Friedel-Crafts acylation of 2-methyl-1-phenylsulfonylindole 6 gave: the 3-acyl derivatives 7 which upon side chain bromination with N-bromosuccinimide (NBS) followed by treatment with primary amines afforded the title compounds 9. Diels-Alder reaction of 9 with dimethyl acetylenedicarboxylate (DMAD) gave the polysubstituted carbazoles 12.
引用
收藏
页码:2663 / 2665
页数:3
相关论文
共 18 条
[1]   SYNTHESES AND DIELS-ALDER CYCLOADDITION REACTIONS OF 4H-FURO[3,4-B]INDOLES - A REGIOSPECIFIC DIELS-ALDER SYNTHESIS OF ELLIPTICINE [J].
GRIBBLE, GW ;
KEAVY, DJ ;
DAVIS, DA ;
SAULNIER, MG ;
PELCMAN, B ;
BARDEN, TC ;
SIBI, MP ;
OLSON, ER ;
BELBRUNO, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5878-5891
[2]   DICHLOROCARBENE-INDUCED DEAMINATION OF NAPHTHALEN-1,4-IMINES AND ANTHRACEN-9,10-IMINES [J].
GRIBBLE, GW ;
ALLEN, RW ;
LEHOULLIER, CS ;
EATON, JT ;
EASTON, NR ;
SLAYTON, RI ;
SIBI, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (05) :1025-1026
[3]  
GRIBBLE GW, 1976, TETRAHEDRON LETT, V17, P3673
[4]   N-BENZOYLINDOLE-2,3-QUINODIMETHANE - DIELS-ALDER REACTIVITY AND SYNTHETIC APPLICATIONS FOR [B]ANNELLATED INDOLES [J].
HABER, M ;
PINDUR, U .
TETRAHEDRON, 1991, 47 (10-11) :1925-1936
[5]   THE INDOLE-2,3-QUINODIMETHANE STRATEGY FOR THE SYNTHESIS OF INDOLE ALKALOIDS [J].
MAGNUS, P ;
GALLAGHER, T ;
BROWN, P ;
PAPPALARDO, P .
ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (01) :35-41
[6]   GENERATION AND CYCLOADDITION REACTIONS OF INDOLE-2,3-QUINODIMETHANES [J].
MARINELLI, ER .
TETRAHEDRON LETTERS, 1982, 23 (27) :2745-2748
[7]   SYNTHESIS OF THE STAUROSPORINE AGLYCONE [J].
MOODY, CJ ;
RAHIMTOOLA, KF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (23) :1667-1668
[8]   SYNTHESIS OF THE CARBAZOLE ALKALOIDS CARBAZOMYCIN-A AND CARBAZOMYCIN-B AND HYELLAZOLE [J].
MOODY, CJ ;
SHAH, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (02) :376-377
[9]   A CONVENIENT SYNTHESIS OF 2-AMINO-6-METHOXY-1-METHYLCARBAZOLE AND 2-AMINO-6-METHOXY-1,4-DIMETHYLCARBAZOLE DERIVATIVES AND THEIR 6-AZA ANALOGS [J].
MORON, J ;
LANDRAS, C ;
BISAGNI, E .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (06) :1573-1576
[10]  
NAGARATHNAM D, 1983, SYNTHESIS-STUTTGART, P156