Pyrroles and Indolizidines from Deprotonated α-(Alkylideneamino)nitriles

被引:11
作者
Schaefer, Ines [1 ,2 ]
Opatz, Till [1 ]
机构
[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany
[2] Univ Hamburg, Dept Chem, D-20146 Hamburg, Germany
来源
SYNTHESIS-STUTTGART | 2011年 / 11期
关键词
heterocycles; carbanions; pyrroles; Umpolung; Michael addition; ONE-POT SYNTHESIS; POLYSUBSTITUTED PYRROLIDINES; AZOMETHINE YLIDES; 2-AZAALLYL ANIONS; SYNTHETIC EQUIVALENTS; ALPHA-AMINONITRILES; CYCLOADDITIONS; KETONES; ESTERS; N-(1-CYANOALKYL)IMINES;
D O I
10.1055/s-0030-1260415
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Their ready availability from simple starting materials in only two synthetic steps and their versatility as building blocks for the construction of highly substituted amines and N-heterocycles renders alpha-(alkylideneamino)nitriles useful synthetic intermediates. Herein, short syntheses of tri- and tetrasubstituted pyrroles including the northern half of the HMG-CoA reductase inhibitor atorvastatin as well as an access to 3-substituted indolizidines will be described.
引用
收藏
页码:1691 / 1704
页数:14
相关论文
共 46 条
[1]   A novel pyrrole synthesis [J].
Agarwal, S ;
Knölker, HJ .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (21) :3060-3062
[3]   SILYL NITRONATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF 3(H-2)-FURANONES [J].
ANDERSEN, SH ;
SHARMA, KK ;
TORSSELL, KBG .
TETRAHEDRON, 1983, 39 (13) :2241-2245
[4]   ORGANOCUPRATES IN A NEW SYNTHESIS OF PURE ENANTIOMERIC AMINO-ACIDS [J].
BAJGROWICZ, JA ;
ELHALLAOUI, A ;
JACQUIER, R ;
PIGIERE, C ;
VIALLEFONT, P .
TETRAHEDRON, 1985, 41 (10) :1833-1843
[5]   Pyrrole syntheses by multicomponent coupling reactions [J].
Balme, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6238-6241
[6]  
BERGNER I, 2009, THESIS U HAMBURG GER
[7]   Modular one-pot synthesis of tetrasubstituted Pyrroles from α-(Alkylideneamino)nitriles [J].
Bergner, Ines ;
Opatz, Till .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7083-7090
[8]   Synthesis of γ-amino acid esters by 1,4-addition of deprotonated α-aminonitriles and α-(alkylideneamino)nitriles to α,β-unsaturated esters [J].
Bergner, Ines ;
Opatz, Till .
SYNTHESIS-STUTTGART, 2007, (06) :918-928
[9]   Cyclocondensation of α-Aminonitriles and Enones: A Short Access to 3,4-Dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-Trisubstituted Pyrroles [J].
Bergner, Ines ;
Wiebe, Christine ;
Meyer, Nino ;
Opatz, Till .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8243-8253
[10]  
Bruylants P., 1924, Bull. Soc. Chim. Belg, V33, P467