A powerful new strategy for diversity-oriented synthesis of pyrroles from donor - Acceptor cyclopropanes and nitriles

被引:112
作者
Yu, M [1 ]
Pagenkopf, BL [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
D O I
10.1021/ol036180+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Lewis acid activated donor-acceptor cyclopropanes react with aliphatic, aromatic, and alpha,beta-unsaturated nitriles in a novel cascade [3 + 2] dipolar cycloaddition, dehydration, and tautomerization sequence to afford pyrroles in moderate to excellent overall yield. This cost-effective and regiospecific method is ideally suited for the preparation of combinatorial libraries.
引用
收藏
页码:5099 / 5101
页数:3
相关论文
共 67 条
[21]   SYNTHESIS OF CYCLIC AND ACYCLIC ENOL ETHERS (VINYL ETHERS) [J].
GASSMAN, PG ;
BURNS, SJ ;
PFISTER, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1449-1457
[22]   GENERAL-METHOD FOR THE SYNTHESIS OF ENOL ETHERS (VINYL ETHERS) FROM ACETALS [J].
GASSMAN, PG ;
BURNS, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5574-5576
[23]   Synthesis of aromatic heterocycles [J].
Gilchrist, TL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (20) :2849-2866
[24]   Synthesis of aromatic heterocycles [J].
Gilchrist, TL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03) :615-628
[25]   Synthesis and applications of β-aminocarboxylic acids containing a cyclopropane ring [J].
Gnad, F ;
Reiser, O .
CHEMICAL REVIEWS, 2003, 103 (04) :1603-1623
[26]   Palladium catalysed synthesis of pyrroles from enamines [J].
Grigg, R ;
Savic, V .
CHEMICAL COMMUNICATIONS, 2000, (10) :873-874
[27]   PALLADIUM(0)-CATALYZED SYNTHESES OF INDOLOQUINONES [J].
HEGEDUS, LS ;
MULHERN, TA ;
MORI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4282-4288
[28]   The synthesis of eta(2)-beta-vinylpyrrole complexes and their conversion to highly substituted indoles [J].
Hodges, LM ;
Spera, ML ;
Moody, MW ;
Harman, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) :7117-7127
[29]  
Hover JA, 2003, HETEROCYCLES, V60, P791
[30]   Efficient one-pot synthesis of polysubstituted pyrroles [J].
Katritzky, AR ;
Huang, TB ;
Voronkov, MV ;
Wang, MY ;
Kolb, H .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8819-8821