Intramolecular cyclization reaction - Palladium(0)-catalyzed cyclization is more effective than tin hydride mediated reaction

被引:32
作者
Majumdar, Krishna C. [1 ]
Debnath, Pradip [1 ]
Taher, Abu [1 ]
Pal, Amarta K. [1 ]
机构
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
关键词
Pd(0) catalyst; CH arylation; intramolecular cyclization; regioselectivity;
D O I
10.1139/V08-023
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Intramolecular CH arylation of pyrone, pyridone, uracil, imidazole, and benzimidazole derivatives are carried out in the presence of a Pd catalyst to form potentially bioactive fused heterocyclic compounds, whereas the n-Bu3SnH-mediated aryl radical cyclization of the precursors 3 afforded mainly halogen-reduced uncyclized products.
引用
收藏
页码:325 / 332
页数:8
相关论文
共 57 条
[1]   Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles [J].
Aldabbagh, F ;
Bowman, WR ;
Mann, E ;
Slawin, AMZ .
TETRAHEDRON, 1999, 55 (26) :8111-8128
[2]   Oxidative radical cyclisations onto imidazoles and pyrroles using Bu3SnH [J].
Aldabbagh, F ;
Bowman, WR ;
Mann, E .
TETRAHEDRON LETTERS, 1997, 38 (45) :7937-7940
[3]   Aromatic homolytic substitution using solid phase synthesis [J].
Allin, SM ;
Bowman, WR ;
Karim, R ;
Rahman, SS .
TETRAHEDRON, 2006, 62 (18) :4306-4316
[4]   Synthetic applications of aryl radical building blocks for cyclisation onto azoles [J].
Allin, SM ;
Bowman, WR ;
Elsegood, MRJ ;
McKee, V ;
Karim, R ;
Rahman, SS .
TETRAHEDRON, 2005, 61 (10) :2689-2696
[5]   Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].
Amatore, C ;
Jutand, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321
[6]  
[Anonymous], PROCESS DEV FINE CHE
[7]   Palladium-catalyzed intramolecular CH arylation of five-membered N-heterocycles [J].
Arai, Nobumichi ;
Takahashi, Masabumi ;
Mitani, Makoto ;
Mori, Atsunori .
SYNLETT, 2006, (18) :3170-3172
[8]   The mechanism of Bu3SnH-mediated homolytic aromatic substitution [J].
Beckwith, ALJ ;
Bowry, VW ;
Bowman, WR ;
Mann, E ;
Parr, J ;
Storey, JMD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :95-98
[9]   Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-lodopyridones, alkynes, and organic halides [J].
Bossharth, E ;
Desbordes, P ;
Monteiro, N ;
Balme, G .
ORGANIC LETTERS, 2003, 5 (14) :2441-2444