Heterocycles from α-Aminonitriles

被引:75
作者
Otto, Nicola [1 ]
Opatza, Till [1 ]
机构
[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, Mainz, Germany
关键词
alpha-aminonitriles; heterocycles; nitrogen heterocycles; synthetic methods; ONE-POT SYNTHESIS; ASYMMETRIC NUCLEOPHILIC ACYLATION; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; 1,3-DIPOLAR CYCLOADDITION REACTIONS; ACYL ANION EQUIVALENTS; CHIRAL AMINO NITRILES; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; CN(R; S); METHOD; POLYSUBSTITUTED PYRROLIDINES;
D O I
10.1002/chem.201403956
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Owing to their various modes of reactivity, alpha-aminonitriles represent versatile building blocks for the construction of a wide range of nitrogen heterocycles. The present Concept article focuses on synthetic methodologies using their bifunctional nature which is the basis of their reactivity as alpha-amino carbanions and as iminium ions. Reactions exclusively taking place on either the amine or on the nitrile moiety will not be considered.
引用
收藏
页码:13064 / 13077
页数:14
相关论文
共 165 条
  • [11] [Anonymous], 2005, ANGEW CHEM INT ED, V44, P5662
  • [12] [Anonymous], 1990, ANGEW CHEM INT ED EN, V29, P179
  • [13] [Anonymous], 1999, ANGEW CHEM INT ED, V38, P2934
  • [14] Imidazolylidenes, imidazolinylidenes and imidazolidines
    Arduengo, AJ
    Krafczyk, R
    Schmutzler, R
    Craig, HA
    Goerlich, JR
    Marshall, WJ
    Unverzagt, M
    [J]. TETRAHEDRON, 1999, 55 (51) : 14523 - 14534
  • [15] Azabicyclic amino acids by stereoselective dearomatizing cyclization of the enolates of N-nicotinoyl glycine derivatives
    Arnott, Gareth
    Clayden, Jonathan
    Hamilton, Stuart D.
    [J]. ORGANIC LETTERS, 2006, 8 (23) : 5325 - 5328
  • [16] 2,4,4-TRISUBSTITUTED 5-AMINO-4H-IMIDAZOLES - A NEW SYNTHETIC APPROACH AND REACTIVITY
    AVENDANO, C
    RAMOS, T
    GOMEZMOLINERO, E
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (02) : 537 - 540
  • [17] NEW 5-AMINOGLYOXALINES AS POTENTIAL ADRENERGIC AGENTS
    BADER, H
    DOWNER, JD
    DRIVER, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1950, (OCT): : 2775 - 2784
  • [18] BARTON DHR, 1990, TETRAHEDRON, V46, P7587
  • [19] Large-scale preparation of 2-methyloxazole-4-carboxaldehyde
    Benoit, Georges-Emmanuel
    Carey, John S.
    Chapman, Alan M.
    Chima, Ranjit
    Hussain, Nigel
    Popkin, Matthew E.
    Roux, Guillaume
    Tavassoli, Bahareh
    Vaxelaire, Carine
    Webb, Michael R.
    Whatrup, David
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (01) : 88 - 95
  • [20] Modular one-pot synthesis of tetrasubstituted Pyrroles from α-(Alkylideneamino)nitriles
    Bergner, Ines
    Opatz, Till
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) : 7083 - 7090