Pseudo-Multicomponent Reactions of Arynes with N-Aryl Imines

被引:31
作者
Castillo, Juan-Carlos [1 ]
Quiroga, Jairo [2 ]
Abonia, Rodrigo [2 ]
Rodriguez, Jean [1 ]
Coquerel, Yoann [1 ]
机构
[1] Aix Marseille Univ, Cent Marseille, CNRS, iSm2 UMR 7313, F-13397 Marseille, France
[2] Univ Valle, Dept Quim, Cali, Colombia
关键词
ARYLATION; INSERTION; TANDEM; ANILINES; BENZYNE; ACCESS;
D O I
10.1021/acs.joc.5b01564
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pseudo-three-component reactions are described for the conversion of simple N-aryl imines into 1,2-dihydroisoquinoline-type products. The approach relies on a regioselective cascade reaction involving two equivalents of the aryne component iteratively as a dienophile and as an electrophile. Some examples of related, more complex pseudo-four-component cascade processes are also reported.
引用
收藏
页码:9767 / 9773
页数:7
相关论文
共 34 条
[1]   An Efficient Synthesis of 7-(Arylmethyl)-3-tert-butyl-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazines [J].
Abonia, Rodrigo ;
Castillo, Juan ;
Insuasty, Braulio ;
Quiroga, Jairo ;
Nogueras, Manuel ;
Cobo, Justo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (33) :6454-6463
[2]   Novel reactions of [2.2]paracyclophane-azomethines with benzyne [J].
Aly, AA ;
Mourad, AFE ;
El-Shaieb, KM ;
Hopf, H .
SYNTHETIC COMMUNICATIONS, 2001, 31 (04) :637-644
[3]   Tandem [4+2]/[2+2] Cycloaddition Reactions Involving Indene or Benzofurans and Arynes [J].
Bhojgude, Sachin Suresh ;
Thangaraj, Manikandan ;
Suresh, Eringathodi ;
Biju, Akkattu T. .
ORGANIC LETTERS, 2014, 16 (13) :3576-3579
[4]   Efficient Synthesis of 9-Aryldihydrophenanthrenes by a Cascade Reaction Involving Arynes and Styrenes [J].
Bhojgude, Sachin Suresh ;
Bhunia, Anup ;
Gonnade, Rajesh G. ;
Biju, Aldcattu T. .
ORGANIC LETTERS, 2014, 16 (03) :676-679
[5]   Stereoselective Multiple Bond-Forming Transformations (MBFTs): The Power of 1,2-and 1,3-Dicarbonyl Compounds [J].
Bonne, Damien ;
Constantieux, Thierry ;
Coquerel, Yoann ;
Rodriguez, Jean .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (07) :2218-2231
[6]   The Aryne aza-Diels-Alder Reaction: Flexible Syntheses of Isoquinolines [J].
Castillo, Juan-Carlos ;
Quiroga, Jairo ;
Abonia, Rodrigo ;
Rodriguez, Jean ;
Coquerel, Yoann .
ORGANIC LETTERS, 2015, 17 (13) :3374-3377
[7]   Synthesis and characterization of oxadisilole-fused phenanthridines and dioxatrisilole-fused phenanthridines from benzyne [J].
Chen, Jingda ;
Chen, Yali ;
Wang, Xueli ;
Kong, Kundi ;
Cao, Weiguo ;
Chen, Jie .
TETRAHEDRON, 2015, 71 (32) :5130-5136
[8]   α-Monoarylation and tandem arylation-insertion of malonates with arynes [J].
Chen, Qian ;
Zhang, Changyuan ;
Chen, Lili ;
Wen, Chunxiao ;
Du, Zhiyun ;
Chen, Huixiong ;
Zhang, Kun .
TETRAHEDRON LETTERS, 2015, 56 (16) :2094-2097
[9]   THE INTERMOLECULAR BENZYNE CYCLO-ADDITION (IBC) APPROACH TO PROTOBERBERINES - HIGHLY CONVERGENT SYNTHESIS OF 8-OXYPSEUDOPALMATINE [J].
COBAS, A ;
GUITIAN, E ;
CASTEDO, L ;
SAA, JM .
TETRAHEDRON LETTERS, 1988, 29 (20) :2491-2492
[10]  
Coquerel Y., 2010, ADV SYNTHETIC CHEM, P187, DOI DOI 10.1002/9783527630554.CH9