Palladium-Catalyzed Domino Cyclization (5-exo/3-exo), Ring-Expansion by Palladium Rearrangement, and Aromatization: An Expedient Synthesis of 4-Arylnicotinates from Morita-Baylis-Hillman Adducts

被引：20
作者：
Kim, Ko Hoon [1 ,2 ]
Kim, Se Hee [1 ,2 ]
Lee, Hyun Ju [1 ,2 ]
Kim, Jae Nyoung [1 ,2 ]
机构：
[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea
[2] Chonnam Natl Univ, Inst Basic Sci, Kwangju 500757, South Korea
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 10期
基金：
新加坡国家研究基金会;
关键词：
4-arylnicotinates; Morita-Baylis-Hillman adducts; palladium; palladium rearrangement; pyridines; REGIOSELECTIVE SYNTHESIS; CROSS-METATHESIS; IN-SITU; DERIVATIVES; ACCESS; EFFICIENT; PYRIDINES; CONSTRUCTION; ELIMINATION; INVERSION;
D O I：
10.1002/adsc.201300211
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Various 4-arylnicotinate derivatives were synthesized via a palladium-catalyzed cascade reaction of N-(2-bromoallyl)-N-cinnamyltosylamides in a one-pot procedure in good yields. The reaction involves a domino 5-exo/3-exo carbopalladation, ring-expansion by palladium rearrangement, and an aromatization process.
引用
收藏
页码：1977 / 1983
页数：7
相关论文
共 59 条
  • [1] Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues
    Banwell, MG
    Crasto, CF
    Easton, CJ
    Karoli, T
    March, DR
    Nairn, MR
    O'Hanlon, PJ
    Oldham, MD
    Willis, AC
    Yue, WM
    [J]. CHEMICAL COMMUNICATIONS, 2001, (21) : 2210 - 2211
  • [2] Recent advances in the Baylis-Hillman reaction and applications
    Basavaiah, D
    Rao, AJ
    Satyanarayana, T
    [J]. CHEMICAL REVIEWS, 2003, 103 (03) : 811 - 891
  • [3] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry
    Basavaiah, Deevi
    Reddy, Bhavanam Sekhara
    Badsara, Satpal Singh
    [J]. CHEMICAL REVIEWS, 2010, 110 (09) : 5447 - 5674
  • [4] Total Synthesis of the Bridged Indole Alkaloid Apparicine
    Bennasar, M. -Lluisa
    Zulaica, Ester
    Sole, Daniel
    Roca, Tomas
    Garcia-Diaz, Davinia
    Alonso, Sandra
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) : 8359 - 8368
  • [5] Sequential ring-closing metathesis-vinyl halide Heck cyclization reactions: access to the tetracyclic ring system of ervitsine
    Bennasar, M-Lluisa
    Zulaica, Ester
    Sole, Daniel
    Alonso, Sandra
    [J]. TETRAHEDRON, 2012, 68 (24) : 4641 - 4648
  • [6] A synthetic entry to 3,5-disubstituted pyridines
    Bennasar, ML
    Zulaica, E
    Roca, T
    Alonso, Y
    Monerris, M
    [J]. TETRAHEDRON LETTERS, 2003, 44 (25) : 4711 - 4714
  • [7] Intramolecular Heck couplings and cycloisomerizations of bromodienes and enynes with 1′,1′-disubstituted methylenecyclopropane terminators:: Efficient syntheses of [3]dendralenes
    Bräse, S
    Wertal, H
    Frank, D
    Vidovic, D
    de Meijere, A
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (19) : 4167 - 4178
  • [8] Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines
    Bull, James A.
    Mousseau, James J.
    Pelletier, Guillaume
    Charette, Andre B.
    [J]. CHEMICAL REVIEWS, 2012, 112 (05) : 2642 - 2713
  • [9] Pd2(dba)3-promoted synthesis of 3-N-substituted 4-aryl-1,2,3,6-tetrahydropyridine
    Chang, Meng-Yang
    Lin, Chung-Han
    Chen, Yeh-Long
    Hsu, Ru-Ting
    Chang, Ching-Yao
    [J]. TETRAHEDRON LETTERS, 2010, 51 (37) : 4886 - 4889
  • [10] Ciganek E., 1997, ORGANIC REACTIONS, V51, S., P201, DOI DOI 10.1002/0471264180.OR051.02
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