PYRROLYL COMPOUNDS OF MAIN GROUP ELEMENTS - SYNTHESIS OF GROUP 14 5-METALATED PYRROLE-2-CARBALDEHYDES

被引:21
作者
DENAT, F [1 ]
GASPARDILOUGHMANE, H [1 ]
DUBAC, J [1 ]
机构
[1] UNIV TOULOUSE 3,ORGANOMET LAB,CNRS,URA 477,118 ROUTE NARBONNE,F-31062 TOULOUSE,FRANCE
关键词
D O I
10.1016/0022-328X(92)83112-U
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New group 14 5-metallated pyrrole-2-carbaldehydes 5-R3E(C4H2NR')CHO (E - Si, Ge, Sn; R = Mc, El, (n)Bu; R' = H, Me) have been regiospecifically prepared from corresponding pyrrole-2-carbaldehydes by either (i) 5-lithiation after protection of the aldehyde function by treatment with lithium N-methylpiperazide or by formation of an azafulvene dimer or (ii) metallation by R3EX (X = Cl, Br). The 5-silylated compound (E = Si, R = R' = Me) has been also obtained from 1-methyl-2,5-bis(trimethylsilyl)pyrrole.
引用
收藏
页码:173 / 182
页数:10
相关论文
共 33 条
[1]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF SOME SUBSTITUTED PYRROLES [J].
ABRAHAM, RJ ;
LAPPER, RD ;
SMITH, KM ;
UNSWORTH, JF ;
ROBINSON, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (09) :1004-1009
[2]   PREPARATION CHEMISTRY AND SPECTRA OF (SILYLMETHYL)PYRROLES [J].
ASHBY, BA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1966, 5 (05) :405-&
[4]   PHOTOISOMERIZATION OF 2-(TRIMETHYLSILYL)PYRROLES [J].
BARTON, TJ ;
HUSSMANN, GP .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5881-5882
[5]   5-CO-ORDINATED SILICON-COMPOUNDS - GEOMETRY OF FORMATION BY INTRAMOLECULAR COORDINATION - CRYSTAL-STRUCTURE OF 2-(DIMETHYLAMINOMETHYL)PHENYL-1-NAPHTHYLSILANE [J].
BOYER, J ;
BRELIERE, C ;
CARRE, F ;
CORRIU, RJP ;
KPOTON, A ;
POIRIER, M ;
ROYO, G ;
YOUNG, JC .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1989, (01) :43-51
[6]   N-(TRIISOPROPYLSILYL)PYRROLE - A PROGENITOR PAR EXCELLENCE OF 3-SUBSTITUTED PYRROLES [J].
BRAY, BL ;
MATHIES, PH ;
NAEF, R ;
SOLAS, DR ;
TIDWELL, TT ;
ARTIS, DR ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6317-6328
[7]   CHEMOSELECTIVE PROTECTION OF HETEROAROMATIC ALDEHYDES AS IMIDAZOLIDINE DERIVATIVES - PREPARATION OF 5-SUBSTITUTED FURAN-2-CARBOXALDEHYDE AND THIOPHENE-2-CARBOXALDEHYDE VIA METALLO-IMIDAZOLIDINE INTERMEDIATES [J].
CARPENTER, AJ ;
CHADWICK, DJ .
TETRAHEDRON, 1985, 41 (18) :3803-3812
[8]  
CHADWICK DJ, 1979, J CHEM SOC PERK T 1, P2845, DOI 10.1039/p19790002845
[9]   LITHIATIONS OF 1-TRIALKYLSILYLPYRROLES - N TO C SILYL GROUP REARRANGEMENT [J].
CHADWICK, DJ ;
HODGSON, ST .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (08) :1833-1836
[10]   ORTHO METALATION DIRECTED BY ALPHA-AMINO ALKOXIDES [J].
COMINS, DL ;
BROWN, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (06) :1078-1083