Unusual dirhodium tetraacetate catalyzed intramolecular cyclization of isoquinoline diazoamides

被引:12
作者
Chelucci, G
Culeddu, N
Saba, A
Valenti, R
机构
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
[2] CNR, Ist Applicaz Tecn Chim Avanzate Problemi Agro, I-07100 Sassari, Italy
关键词
D O I
10.1016/S0040-4039(99)01738-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The dirhodium(II) tetraacetate catalyzed decomposition of an isoquinoline diazoamide leads to the unexpected formation of a 1,3-oxazin-4-one ring which is consistent with a rare example of an intramolecular metal-carbene hydride-abstraction mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8269 / 8270
页数:2
相关论文
共 9 条
[1]   STEREOSPECIFIC COURSE OF A TRANSANNULAR C-H INSERTION PROCESS [J].
CHELUCCI, G ;
SABA, A ;
VALLE, G .
TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :807-810
[2]   Catalytic decomposition of enantiomerically pure 3-methyl and 3-phenyl-6-diazo-4 methyloxazepan-5,7-diones [J].
Chelucci, G ;
Saba, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (05) :699-702
[3]   INTRAMOLECULAR C-H INSERTION OR STYRENE CYCLOPROPANATION IN CATALYTIC DECOMPOSITION OF DICYCLOHEXYLDIAZOMALONIC ESTERS [J].
CHELUCCI, G ;
SABA, A .
TETRAHEDRON LETTERS, 1995, 36 (26) :4673-4676
[4]   (S)-(+)-1,5-DIMETHYL-4-PHENYL-1,5-DIHYDRO-2H-PYRROL-2-ONE AND (R)-(-)-1,5-DIMETHYL-4-PHENYL-1,5-DIHYDRO-2H-PYRROL-2-ONE BY CARBENE RING CONTRACTION AND DECARBOXYLATION OF (2R,3S)(-)-6-DIAZO-3,4-DIMETHYL-2-PHENYLOXAZEPANE-5,7-DIONE AND (2S,3R)-(+)-6-DIAZO-3,4-DIMETHYL-2-PHENYLOXAZEPANE-5,7-DIONE [J].
CHELUCCI, G ;
SABA, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (01) :78-79
[5]  
Doyle M. P., 1997, MODERN CATALYTIC MET
[6]   A NEW CATALYTIC TRANSFORMATION OF DIAZO ESTERS - HYDRIDE ABSTRACTION IN DIRHODIUM(II)-CATALYZED REACTIONS [J].
DOYLE, MP ;
DYATKIN, AB ;
AUTRY, CI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (06) :619-621
[7]   DIRHODIUM TETRAACETATE CATALYZED CARBON-HYDROGEN INSERTION REACTION IN N-SUBSTITUTED ALPHA-CARBOMETHOXY-ALPHA-DIAZOACETANILIDES AND STRUCTURAL ANALOGS - SUBSTITUENT AND CONFORMATIONAL EFFECTS [J].
WEE, AGH ;
LIU, BS ;
ZHANG, L .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) :4404-4414
[8]   ORGANIC-SYNTHESIS WITH ALPHA-DIAZOCARBONYL COMPOUNDS [J].
YE, T ;
MCKERVEY, MA .
CHEMICAL REVIEWS, 1994, 94 (04) :1091-1160
[9]   RHODIUM(II) ACETATE-CATALYZED DECOMPOSITION OF 2-DIAZO-3-OXOBUTANAMIDES DERIVED FROM L-PHENYLALANINE [J].
ZARAGOZA, F ;
ZAHN, G .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1995, 337 (04) :292-298