SYNTHESIS OF PHENANTHROPYRROLES AND PHENANTHROLINOPYRROLES FROM ISOCYANOACETATES - AN EXTENSION OF THE BARTON-ZARD PYRROLE CONDENSATION

被引:55
作者
LASH, TD
NOVAK, BH
LIN, YN
机构
[1] Department of Chemistry, Illinois State University, Normal
关键词
D O I
10.1016/S0040-4039(00)77152-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
9-Nitrophenanthrene (1) and 5-nitro-1,10-phenanthroline (4) condensed with esters of isocyanoacetic acid in the presence of one equivalent of DBU to give the corresponding phenanthropyrroles 2 and phenantholinopyrroles 5, respectively, in excellent yields.
引用
收藏
页码:2493 / 2494
页数:2
相关论文
共 24 条
[1]  
BARTON DHR, 1990, TETRAHEDRON, V46, P7587
[2]   A NEW SYNTHESIS OF PYRROLES FROM NITROALKENES [J].
BARTON, DHR ;
ZARD, SZ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1098-1100
[3]  
BUADER C, 1992, TETRAHEDRON, V48, P5135
[4]   ELECTROPHILIC SUBSTITUTION .3. THE NITRATION OF PHENANTHRENE [J].
DEWAR, MJS ;
WARFORD, EWT .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (SEP) :3570-3572
[5]  
Hartman G. D., 1980, ORG SYNTH, V59, P183
[6]  
Jackson A.H., 1973, TOTAL SYNTHESIS NATU, V1, P143
[7]  
Jackson A. H., 1984, TOTAL SYNTHESIS NATU, V6, P237
[8]   AN IMPROVED SYNTHESIS OF PYRROLES FROM N-PARA-TOLUENESULFONYLGLYCINE ESTERS AND ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES [J].
LASH, TD ;
HOEHNER, MC .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (07) :1671-1676
[9]   GEOCHEMICAL ORIGINS OF SEDIMENTARY BENZOPORPHYRINS AND TETRAHYDROBENZOPORPHYRINS [J].
LASH, TD .
ENERGY & FUELS, 1993, 7 (02) :166-171
[10]   INFLUENCE OF CARBOCYCLIC RINGS ON PORPHYRIN CYCLIZATIONS - SYNTHESIS OF GEOCHEMICALLY SIGNIFICANT CYCLOALKANOPORPHYRINS [J].
LASH, TD ;
BALASUBRAMANIAM, RP ;
CATARELLO, JJ ;
JOHNSON, MC ;
MAY, DA ;
BLADEL, KA ;
FEELEY, JM ;
HOEHNER, MC ;
MARRON, TG ;
NGUYEN, TH ;
PERUN, TJ ;
QUIZON, DM ;
SHINER, CM ;
WATSON, A .
ENERGY & FUELS, 1990, 4 (06) :668-674