A direct synthesis of 1-aryl- and 1-alkenylcyclopropylamines from aryl and alkenyl nitriles

被引:64
|
作者
Bertus, P [1 ]
Szymoniak, J [1 ]
机构
[1] Univ Reims, CNRS, UMR 6519, F-51687 Reims 2, France
来源
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 18期
关键词
D O I
10.1021/jo034710+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of various aromatic nitriles with 1.1 equiv of Ti(Oi-Pr)(4) and 2.2 equiv of EtMgBr followed by addition of a Lewis acid gave 1-aryl cyclopropylamines in 43-76% yields. Under similar conditions, conjugated alkene-nitriles afford 1-alkenylcyclopropylamines (42-65%).
引用
收藏
页码:7133 / 7136
页数:4
相关论文
共 50 条
  • [31] Synthesis of homophthalimide spironaphthalenones through [5+1] spiroannulation of aryl/alkenyl enaminones with diazo homophthalimides
    Yang, Chun
    Zhang, Xinying
    Fan, Xuesen
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (17) : 4282 - 4288
  • [32] 1,5-hydrogen atom transfer from α, β and γ carbons to an alkenyl or aryl radical in cycloalkanones
    Sha, CK
    Ho, WY
    Mohanakrishnan, AK
    Lin, CL
    Chu, SY
    COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE, 2001, 4 (06): : 439 - 442
  • [33] Alkenyl alane-pyridine complexes in a new synthesis of aryl alk-1-enyl sulfoxides
    Signore, G.
    Calderisi, M.
    Malanga, C.
    Menicagli, R.
    TETRAHEDRON, 2007, 63 (01) : 177 - 182
  • [34] Magnesium amide-promoted one-pot synthesis of aryl amides from aryl nitriles and carboxylic acids
    Cherukuri, S
    Villarreal, V
    Muramulla, S
    Sanchez, R
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U504 - U504
  • [35] Novel synthesis of 1-aryl-1-trifluoromethylallenes
    Han, HY
    Kim, MS
    Son, JB
    Jeong, IH
    TETRAHEDRON LETTERS, 2006, 47 (02) : 209 - 212
  • [36] SYNTHESIS OF (1-ARYL-1-ALKYLETHYL)ALKOXYAMINES
    STEWART, AO
    MARTIN, JG
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05): : 1221 - 1223
  • [37] Synthesis of α-Aryl Primary Amides from α-Silyl Nitriles and Aryl Sulfoxides through [3,3]-Sigmatropic Rearrangement
    Luo, Fan
    Zhou, Hui
    Chen, Xiao-Bei
    Liu, Xue-Jun
    Chen, Xiao-Dong
    Qian, Peng-Fei
    Wu, Xin-Ping
    Wang, Wei
    Zhang, Shi-Lei
    ORGANIC LETTERS, 2022, 24 (08) : 1700 - 1705
  • [38] Redox reaction between benzyl azides and aryl azides: concerted synthesis of aryl nitriles and anilines
    Kim, Yongjin
    Rhee, Young Ho
    Park, Jaiwook
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (07) : 1636 - 1641
  • [39] Direct Synthesis of Aryl Ketones by Palladium-Catalyzed Desulfinative Addition of Sodium Sulfinates to Nitriles
    Liu, Jing
    Zhou, Xianya
    Rao, Honghua
    Xiao, Fuhong
    Li, Chao-Jun
    Deng, Guo-Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (29) : 7996 - 7999
  • [40] Synthesis of [11C]aryl nitriles via [11C]aryl amides
    Gonzalez, Miguel Cortes
    Schou, Magnus
    NUCLEAR MEDICINE AND BIOLOGY, 2022, 108 : S71 - S71