Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines:: An easy entry into 2,3-disubstituted furopyridines

被引:155
作者
Arcadi, A
Cacchi, S
Di Giuseppe, S
Fabrizi, G
Marinelli, F
机构
[1] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, Fac Sci, I-67100 Laquila, Italy
[2] Univ Roma La Sapienza, Sostanze Biologicamente Attive, Dipartimento Studi Chim & Tecnol, I-00185 Rome, Italy
关键词
D O I
10.1021/ol0261581
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] 2,3-Disubstituted furo[3,2-b]pyridines, 2,3-disubstituted furo[2,3-b]pyridines, and 2,3-disubstituted furo[2,3-c]pyridines are readily prepared under mild conditions via the palladium-catalyzed cross-coupling of 1-alkynes with o-lodoacetoxy- or o-iodobenzyloxypyridines, followed by electrophilic cyclization by I-2 or by PdCl2 under a balloon of carbon monoxide.
引用
收藏
页码:2409 / 2412
页数:4
相关论文
共 35 条
[1]   Fibrillogenesis of β-amyloid [J].
Allsop, D ;
Howlett, D ;
Christie, G ;
Karran, E .
BIOCHEMICAL SOCIETY TRANSACTIONS, 1998, 26 (03) :459-463
[2]  
Arcadi A, 2002, SYNLETT, P453
[3]   THE PALLADIUM-CATALYZED SYNTHESIS OF 2,3,5-TRISUBSTITUTED FURANS FROM 2-PROPARGYL-1,3-DICARBONYL COMPOUNDS AND VINYLIC OR ARYL TRIFLATES OR HALIDES [J].
ARCADI, A ;
CACCHI, S ;
LAROCK, RC ;
MARINELLI, F .
TETRAHEDRON LETTERS, 1993, 34 (17) :2813-2816
[4]   Palladium-catalyzed reaction of o-ethynylphenols, o-((trimethylsilyl)ethynyl)phenyl acetates, and o-alkynylphenols with unsaturated triflates or halides: A route to 2-substituted-, 2,3-disubstituted-, and 2-substituted-3-acylbenzo[b]furans [J].
Arcadi, A ;
Cacchi, S ;
DelRosario, M ;
Fabrizi, G ;
Marinelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9280-9288
[5]  
ARCADI A, 1986, SYNTHESIS-STUTTGART, P749
[6]  
Arcadi A, 2000, SYNLETT, P1464
[7]   A novel route to 6-substituted and 5,6-disubstituted 2-pyrones [J].
Bellina, F ;
Biagetti, M ;
Carpita, A ;
Rossi, R .
TETRAHEDRON LETTERS, 2001, 42 (15) :2859-2863
[8]   Selective synthesis of natural and unnatural 5,6-disubstituted 2(2H)-pyranones via iodolactonization of 5-substituted (Z)-2-en-4-ynoic acids [J].
Bellina, F ;
Biagetti, M ;
Carpita, A ;
Rossi, R .
TETRAHEDRON, 2001, 57 (14) :2857-2870
[9]   A brief synthesis of beta-iodofurans [J].
Bew, SP ;
Knight, DW .
CHEMICAL COMMUNICATIONS, 1996, (09) :1007-1008
[10]  
Cho SY, 1996, HETEROCYCLES, V43, P1641