Nitrogenous educts through oxidative amidation of phenols: The bimolecular reaction

被引:60
作者
Canesi, S
Bouchu, D
Ciufolini, MA
机构
[1] Univ Lyon 1, CNRS, UMR 5181, Lab Synth & Methodol Organ, F-69622 Villeurbanne, France
[2] Ecole Super Chim Phys & Elect, F-69622 Villeurbanne, France
[3] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
关键词
D O I
10.1021/ol048094v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The elusive oxidative amidation of phenols to 4-aza-substituted dienones in the bimolecular mode may be achieved by treatment with iodobenzene diacetate ("DIB") in a mixture of hexafluoro-2-propanol and acetonitrile.
引用
收藏
页码:175 / 177
页数:3
相关论文
共 30 条
[1]   New oxidative transformations of phenolic and indolic oxazolines: An avenue to useful azaspirocyclic building blocks [J].
Braun, NA ;
Ousmer, M ;
Bray, JD ;
Bouchu, D ;
Peters, K ;
Peters, EM ;
Ciufolini, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4397-4408
[2]   Synthesis of spirolactams from tyrosine amides and related substances [J].
Braun, NA ;
Ciufolini, MA ;
Peters, K ;
Peters, EM .
TETRAHEDRON LETTERS, 1998, 39 (26) :4667-4670
[3]   Fully stereocontrolled total syntheses of (-)-cylindricine C and (-)-2-epicylindricine C: A departure in sulfonamide chemistry [J].
Canesi, S ;
Bouchu, D ;
Ciufolini, MA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (33) :4336-4338
[4]   Efficient oxidative spirocyclization of phenolic sulfonamides [J].
Canesi, S ;
Belmont, P ;
Bouchu, D ;
Rousset, L ;
Ciufolini, MA .
TETRAHEDRON LETTERS, 2002, 43 (29) :5193-5195
[5]  
CANESI S, 2004, ANGEW CHEM, V116, P4436
[6]   Reactive dienes: Intramolecular aromatic oxidation of 3-(2-hydroxyphenyl)-propionic acids [J].
Drutu, I ;
Njardarson, JT ;
Wood, JL .
ORGANIC LETTERS, 2002, 4 (04) :493-496
[7]   N-IODO-AMIDES - CYCLIZATION OF SUBSTITUTED BIPHENYL-2-CARBOXAMIDES [J].
GLOVER, SA ;
GOOSEN, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (06) :653-657
[8]   N-ALKOXY-N-ACYLNITRENIUM IONS IN INTRAMOLECULAR AROMATIC ADDITION-REACTIONS [J].
GLOVER, SA ;
GOOSEN, A ;
MCCLELAND, CW ;
SCHOONRAAD, JL .
TETRAHEDRON, 1987, 43 (11) :2577-2592
[9]   THE NITRATION OF 4-METHYLPHENOL, 3,4-DIMETHYLPHENOL AND 3,4,5-TRIMETHYLPHENOL WITH NITROGEN-DIOXIDE [J].
HARTSHORN, MP ;
JUDD, MC ;
VANNOORT, RW ;
WRIGHT, GJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (05) :689-697
[10]  
HASHIMOTO Y, 1979, TETRAHEDRON LETT, P1611