Expeditious Synthesis of Highly Substituted Indolizinones via a Palladium-Catalyzed Domino Sequence

被引:48
作者
Kim, Ikyon [1 ]
Kim, Kyungsun [1 ]
机构
[1] Korea Res Inst Chem Technol, Med Chem Res Ctr, Taejon 305600, South Korea
关键词
EFFICIENT SYNTHESIS; ORGANIC HALIDES; O-ALKYNYLPHENOLS; STRATEGIC USE; CONSTRUCTION; HETEROCYCLES; CYCLIZATION; ALKYNES; BONDS; ARYL;
D O I
10.1021/ol1006778
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct one-pot approach to polysubstituted indolizinones from tertiary propargylic alcohols using a palladium-catalyzed domino process involving aminopalladation, reductive elimination, and 1,2-shift is described.
引用
收藏
页码:2500 / 2503
页数:4
相关论文
共 39 条
[1]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[2]   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
[3]   Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[4]   Cyclisations involving attack of carbo- and heteronucleophiles on carbon-carbon π-bonds activated by organopalladium complexes [J].
Balme, G ;
Bouyssi, D ;
Lomberget, T ;
Monteiro, N .
SYNTHESIS-STUTTGART, 2003, (14) :2115-2134
[5]  
Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671
[6]   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
[7]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[8]   2,3-disubstituted indoles through the palladium-catalyzed reaction of aryl chlorides with o-alkynyltrifluoroacetanilides [J].
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Goggiamani, Antonella .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (10-11) :1301-1305
[9]   Efficient synthesis of highly substituted indolizinones via iodocyclization and 1,2-shift [J].
Choi, Jihyun ;
Lee, Ge Hyeong ;
Kim, Ikyon .
SYNLETT, 2008, (08) :1243-1249
[10]   Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of 2-(1-alkynyl)benzaldimines and organic halides [J].
Dai, GX ;
Larock, RC .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :920-928