Reductive alkylation of aromatic amines with enol ethers

被引:13
作者
Reddy, TJ [1 ]
Leclair, M [1 ]
Proulx, M [1 ]
机构
[1] Virochem Pharma Inc, Laval, PQ H7V 4A7, Canada
关键词
reductive alkylation; aromatic amines; 2-methoxypropene; trimethylsilylenol ethers; sodium triacetoxyborohydride;
D O I
10.1055/s-2005-863704
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reductive alkylation of aromatic amines with 2-methoxypropene using 1.0 equivalent of HOAc and NaBH(OAc)(3) in 1,2-dichloroethane (DCE) at room temperature furnished N-isopropyl amines in 50-98% yields. This method was successfully extended to trimethylsilyl enol ethers. The mild reaction conditions provide a new alternative procedure for the reductive amination of electron deficient aromatic amines.
引用
收藏
页码:583 / 586
页数:4
相关论文
共 50 条
[21]   Continuous flow Reductive Alkylation of Methanol by Aldehydes. Synthesis of O-Methyl Ethers and 1,1-Dimethoxyacetals [J].
Radjagobalou, Robbie ;
Rouffeteau, Virgile ;
Deleu, Alexia ;
Nabokoff, Pierre ;
Cossy, Janine ;
Len, Christophe .
MOLECULAR CATALYSIS, 2022, 524
[22]   BROMINATION OF AROMATIC AMINES [J].
Mustafayeva, F. A. ;
Kakhramanov, N. T. .
IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, 2019, 62 (04) :47-59
[23]   Effective parameters on reaction of reductive alkylation of acetylhydrazine [J].
Pakdehi, SG ;
Moghaddam, AS ;
Farahani, MF ;
Mofrad, RT ;
Alamdari, RF ;
Abolhamd, G .
THEORY AND PRACTICE OF ENERGETIC MATERIALS, VOL 5, PARTS A AND B, 2003, :499-503
[24]   Rapid and convenient microwave-assisted synthesis of primary amines via reductive n-alkylation of methyl carbamate with aldehydes [J].
Lehmann, Fredrik ;
Scobie, Martin .
SYNTHESIS-STUTTGART, 2008, (11) :1679-1681
[25]   Direct reductive alkylation of amino acids: Synthesis of bifunctional chelates for nuclear imaging [J].
Levadala, MK ;
Banerjee, SR ;
Maresca, KP ;
Babich, JW ;
Zubieta, J .
SYNTHESIS-STUTTGART, 2004, (11) :1759-1766
[26]   Intramolecular radical non-reductive alkylation of ketones via transient enamines [J].
Diaba, Faiza ;
Montiel, Juan A. ;
Bonjoch, Josep .
CHEMICAL COMMUNICATIONS, 2016, 52 (97) :14031-14034
[27]   Alkylation of Amines with Alcohols and Amines by a Single Catalyst under Mild Conditions [J].
Zou, Qingzhu ;
Wang, Chao ;
Smith, Jen ;
Xue, Dong ;
Xiao, Jianliang .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (27) :9656-9661
[28]   Haemoglobin adducts of aromatic amines: diamines and polyaromatic amines [J].
Sabbioni, G ;
Beyerbach, A .
JOURNAL OF CHROMATOGRAPHY B, 2000, 744 (02) :377-387
[29]   Chitosan derivatives with thickening properties obtained by reductive alkylation [J].
Alves, Keila dos Santos ;
Lima Vidal, Rosangela Regia ;
Balaban, Rosangela de Carvalho .
MATERIALS SCIENCE & ENGINEERING C-BIOMIMETIC AND SUPRAMOLECULAR SYSTEMS, 2009, 29 (02) :641-646
[30]   Chromium-Catalyzed Alkylation of Amines by Alcohols [J].
Kallmeier, Fabian ;
Fertig, Robin ;
Irrgang, Torsten ;
Kempe, Rhett .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) :11789-11793