An abnormal Barton-Zard reaction leading to the pyrrolo[2,3-b]indole ring system

被引:56
作者
Pelkey, ET [1 ]
Chang, L [1 ]
Gribble, GW [1 ]
机构
[1] DARTMOUTH COLL,DEPT CHEM,HANOVER,NH 03755
关键词
D O I
10.1039/cc9960001909
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of 3-nitro-N-(phenylsulfonyl)indole 1 with ethyl isocyanoacetate 2 under the Barton-Zard pyrrole synthesis conditions gives ethyl 8-(phenylsulfonyl)-1,8-dihydropyrrolo[2,3-b]indole-2-carboxylate 3 rather than the anticipated ethyl 4-(phenylsulfonyl)-2,4-dihydropyrrolo[3,4-b]indole-3-carboxylate 4.
引用
收藏
页码:1909 / 1910
页数:2
相关论文
共 34 条
[1]   A CONVENIENT SYNTHESIS OF 2-CYANOPYRROLES FROM ISOCYANOACETONITRILE [J].
ADAMCZYK, M ;
REDDY, RE .
TETRAHEDRON LETTERS, 1995, 36 (44) :7983-7986
[2]  
[Anonymous], 1990, ADV HETEROCYCLIC NAT
[3]  
BARTON DHR, 1990, TETRAHEDRON, V46, P7587
[4]   A NEW SYNTHESIS OF PYRROLES FROM NITROALKENES [J].
BARTON, DHR ;
ZARD, SZ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1098-1100
[5]   TOTAL SYNTHESIS OF CYCLOPENTENOPORPHYRINS OF SEDIMENTARY ORIGIN - DEOXOPHYLLOERYTHROETIOPORPHYRIN, CHLOROPHYLL-C FOSSILS AND RELATED-COMPOUNDS [J].
BAUDER, C ;
OCAMPO, R ;
CALLOT, HJ .
TETRAHEDRON, 1992, 48 (24) :5135-5150
[6]   A REGIOSELECTIVE DIELS-ALDER SYNTHESIS OF ELLIPTICINE [J].
DAVIS, DA ;
GRIBBLE, GW .
TETRAHEDRON LETTERS, 1990, 31 (08) :1081-1084
[7]   PYRROINDOMYCINS, NOVEL ANTIBIOTICS PRODUCED BY STREPTOMYCES-RUGOSPORUS SP LL-42D005 .1. ISOLATION AND STRUCTURE DETERMINATION [J].
DING, WD ;
WILLIAMS, DR ;
NORTHCOTE, P ;
SIEGEL, MM ;
TSAO, R ;
ASHCROFT, J ;
MORTON, GO ;
ALLURI, M ;
ABBANAT, D ;
MAIESE, WM ;
ELLESTAD, GA .
JOURNAL OF ANTIBIOTICS, 1994, 47 (11) :1250-1257
[8]  
DYKER G, 1988, CHEM ZTG, V112, P235
[9]  
GRIBBLE GW, 1991, SYNLETT, P289
[10]   SYNTHESIS AND DIELS-ALDER REACTIONS OF 1,3-DIMETHYL-4-(PHENYLSULFONYL)-4H-FURO[3,4-B]INDOLE - A NEW ANNULATION STRATEGY FOR THE CONSTRUCTION OF ELLIPTICINE AND ISOELLIPTICINE [J].
GRIBBLE, GW ;
SAULNIER, MG ;
SIBI, MP ;
OBAZANUTAITIS, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4518-4523