Two-Component Approach Toward a Fully Substituted N-Fused Pyrrole Ring

被引:92
作者
Chernyak, Dmitri [1 ]
Skontos, Cathy [1 ]
Gevorgyan, Vladimir [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
基金
美国国家卫生研究院;
关键词
CATALYZED CYCLOISOMERIZATION; EFFICIENT SYNTHESIS; CONTAINING HETEROCYCLES; EXPEDITIOUS SYNTHESIS; TOPOISOMERASE-I; LAMELLARIN-D; INDOLIZINES; DERIVATIVES; CYCLIZATION;
D O I
10.1021/ol1011949
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient two-component palladium-catalyzed arylation/cyclization cascade approach toward a variety of N-fused pyrroloheterocycles has been developed. This transformation proceeds via the palladium-catalyzed coupling of aryl halides with propargylic esters or ethers followed by the 5-endo-dig cyclization leading to highly functionalized pyrroloheterocycles in good to excellent yield.
引用
收藏
页码:3242 / 3245
页数:4
相关论文
共 25 条
[1]  
Bailly Christian, 2004, Current Medicinal Chemistry - Anti-Cancer Agents, V4, P363, DOI 10.2174/1568011043352939
[2]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[3]   Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles [J].
Chernyak, Dmitri ;
Gadamsetty, Surendra Babu ;
Gevorgyan, Vladimir .
ORGANIC LETTERS, 2008, 10 (11) :2307-2310
[4]   Cytotoxicities and Structure-Activity Relationships of Natural and Unnatural Lamellarins toward Cancer Cell Lines [J].
Chittchang, Montakarn ;
Batsomboon, Paratchata ;
Ruchirawat, Somsak ;
Ploypradith, Poonsakdi .
CHEMMEDCHEM, 2009, 4 (03) :457-465
[5]  
Facompré M, 2003, CANCER RES, V63, P7392
[6]   Lamellarins and related pyrrole-derived alkaloids from marine organisms [J].
Fan, Hui ;
Peng, Jiangnan ;
Hamann, Mark T. ;
Hu, Jin-Feng .
CHEMICAL REVIEWS, 2008, 108 (01) :264-287
[7]   Electronic effects in the pt-catalyzed cycloisomerization of propargylic esters: Synthesis of 2,3-disubstituted indolizines as a mechanistic probe [J].
Hardin, Alison R. ;
Sarpong, Richmond .
ORGANIC LETTERS, 2007, 9 (22) :4547-4550
[8]   Synthesis and structure-activity relationship study of lamellarin derivatives [J].
Ishibashi, F ;
Tanabe, S ;
Oda, T ;
Iwao, M .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (04) :500-504
[9]   A novel Cu-assisted cycloisomerization of alkynyl imines: Efficient synthesis of pyrroles and pyrrole-containing heterocycles [J].
Kel'in, AV ;
Sromek, AW ;
Gevorgyan, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :2074-2075
[10]   A novel and efficient approach to highly substituted indolizines via 5-endo-trig iodocyclization [J].
Kim, Ikyon ;
Won, Hye Kyoung ;
Choi, Jihyun ;
Lee, Ge Hyeong .
TETRAHEDRON, 2007, 63 (52) :12954-12960