Synthesis of benzofulvenes through chemoselective Sonogashira and Barluenga couplings of ortho ethynyl-N-tosylhydrazones and cycloisomerization

被引:10
作者
Aziz, Jessy [1 ]
Brion, Jean-Daniel [1 ]
Alami, Mouad [1 ]
Hamze, Abdallah [1 ]
机构
[1] Univ Paris 11, CNRS, BioCIS UMR 8076,Fac Pharm, Lab Chim Therapeut,Equipe Labellisee Ligue Canc,L, F-92296 Chatenay Malabry, France
关键词
BOND FORMATION; 3-SUBSTITUTED INDAZOLES; METAL CARBENE; ARYL HALIDES; DERIVATIVES; HYDRAZONES; AMINES; ROUTE;
D O I
10.1039/c5ra14459k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chemoselective synthesis of ortho ethynylhydrazones 7 derived from 2-iodoacetophenone via a Sonogashira coupling is reported for the first time. In this challenging transformation, a site-selective coupling in the presence of a hydrazone function was developed. These compounds represent useful intermediates for the synthesis of benzofulvenes through a sequence of palladium-catalyzed cross-coupling and palladium-catalyzed 5-exo-dig cyclization.
引用
收藏
页码:74391 / 74398
页数:8
相关论文
共 24 条
[1]   Copper-Catalyzed Coupling of N-Tosylhydrazones with Amines: Synthesis of Fluorene Derivatives [J].
Aziz, Jessy ;
Frison, Gilles ;
Gomez, Montserrat ;
Brion, Jean-Daniel ;
Hamze, Abdallah ;
Alami, Mouad .
ACS CATALYSIS, 2014, 4 (12) :4498-4503
[2]   Gold versus Palladium: A Regioselective Cycloisomerization of Aromatic Enynes [J].
Aziz, Jessy ;
Frison, Gilles ;
Le Menez, Patrick ;
Brion, Jean-Daniel ;
Hamze, Abdallah ;
Alami, Mouad .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (17) :3425-3436
[3]   Copper Acetoacetonate [Cu(acac)2]/BINAP-Promoted Csp3-N Bond Formation via Reductive Coupling of N-Tosylhydrazones with Anilines [J].
Aziz, Jessy ;
Brion, Jean-Daniel ;
Hamze, Abdallah ;
Alami, Mouad .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) :2417-2429
[4]   THE DECOMPOSITION OF TOLUENE-PARA-SULPHONYLHYDRAZONES BY ALKALI [J].
BAMFORD, WR ;
STEVENS, TS .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (DEC) :4735-4740
[5]   Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].
Barluenga, Jose ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500
[6]   Tosylhydrazide-Promoted Palladium-Catalyzed Reaction of β-Aminoketones with o-Dihaloarenes: Combining Organocatalysis and Transition-Metal Catalysis [J].
Barluenga, Jose ;
Quinones, Noelia ;
Cabal, Maria-Paz ;
Aznar, Fernando ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (10) :2350-2353
[7]   Pd-Catalyzed Reaction of Sterically Hindered Hydrazones with Aryl Halides: Synthesis of Tetra-Substituted Olefins Related to iso-Combretastatin A4 [J].
Brachet, Etienne ;
Hamze, Abdallah ;
Peyrat, Jean-Francois ;
Brion, Jean-Daniel ;
Alami, Mouad .
ORGANIC LETTERS, 2010, 12 (18) :4042-4045
[8]  
Creary X., 1986, ORG SYNTH, V64, P207, DOI DOI 10.15227/ORGSYN.064.0207
[9]   Copper-catalyzed reductive coupling of tosylhydrazones with amines: A convenient route to α-branched amines [J].
Hamze, Abdallah ;
Treguier, Bret ;
Brion, Jean-Daniel ;
Alami, Mouad .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (18) :6200-6204
[10]   Auto-Tandem Catalysis: Synthesis of Acridines by Pd-Catalyzed C=C Bond Formation and C(sp2)-N Cross-Coupling [J].
Huang, Zhongxing ;
Yang, Yang ;
Xiao, Qing ;
Zhang, Yan ;
Wang, Jianbo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (33) :6586-6593