Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-lodopyridones, alkynes, and organic halides

被引:83
作者
Bossharth, E
Desbordes, P
Monteiro, N
Balme, G
机构
[1] Univ Lyon 1, CNRS, UMR 5622, Lab Chim Organ 1, F-69622 Villeurbanne, France
[2] Bayer CropSci, F-69623 Lyon, France
关键词
D O I
10.1021/ol034644y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic The one-pot assembly of 4-alkoxy-3-iodo-2-pyridones, terminal alkynes, and organic halides has been achieved by integration of two sequential palladium-mediated cross-coupling reactions-Sonogashira and Wacker-type heteroannulation processes-and subsequent deprotection of the alkoxy group to afford furo[2,3-b]pyridones.
引用
收藏
页码:2441 / 2444
页数:4
相关论文
共 52 条
[1]   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
[2]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[3]   Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes [J].
Asao, N ;
Nogami, T ;
Takahashi, K ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :764-765
[4]   Three-component one-pot synthesis of functionalised (Z)-4-benzylidene (and alkenylidene) pyrrolidines [J].
Azoulay, S ;
Monteiro, N ;
Balme, G .
TETRAHEDRON LETTERS, 2002, 43 (51) :9311-9314
[5]  
BALME G, 2002, HDB ORGANOPALLADIUM, P2245
[6]   A PRACTICAL SYNTHESIS OF 5-(CHLOROMETHYL)FURO[2,3-B]PYRIDINE, A KEY INTERMEDIATE FOR THE HIV PROTEASE INHIBITOR, L-754,394 [J].
BHUPATHY, M ;
CONLON, DA ;
WELLS, KM ;
NELSON, JR ;
REIDER, PJ ;
ROSSEN, K ;
SAGER, JW ;
VOLANTE, RP ;
DORSEY, BD ;
HOFFMAN, JM ;
JOSEPH, SA ;
MCDANIEL, SL .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (04) :1283-1287
[7]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[8]  
2-A
[9]   A versatile palladium-mediated three-component reaction for the one-pot synthesis of stereodefined 3-arylidene-(or 3-alkenylidene-)tetrahydrofurans [J].
Bottex, M ;
Cavicchioli, M ;
Hartmann, B ;
Monteiro, N ;
Balme, G .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :175-179
[10]   A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-knorr sequence [J].
Braun, RU ;
Zeitler, K ;
Muller, TJJ .
ORGANIC LETTERS, 2001, 3 (21) :3297-3300