Study on the propylphosphonic anhydride (T3P®) mediated Ugi-type three-component reaction. Efficient synthesis of an α-amino amide library

被引：15
|
作者：
Milen, Matyas [1 ]
Dancso, Andras [1 ]
Foldesi, Tamas [1 ]
Volk, Balazs [1 ]
机构：
[1] Egis Pharmaceut Plc, Directorate Drug Subst Dev, POB 100, H-1475 Budapest, Hungary
来源：
TETRAHEDRON | 2017年 / 73卷 / 01期
关键词：
Multicomponent reaction; Three-component Ugi reaction; alpha-Amino amides; T3P (R); Mechanism; DIRECT IMINE ACYLATION; MULTICOMPONENT REACTIONS; CHEMISTRY; DERIVATIVES; ISOCYANIDES; ISONITRILE; AMIDINES;
D O I：
10.1016/j.tet.2016.11.059
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the present work, a mild and simple synthesis of alpha-amino amides has been developed via the one-pot three-component ABC type Ugi reaction of a wide variety of aromatic aldehydes and primary aromatic amines, and two different aliphatic isocyanides. The reactions took place rapidly at room temperature in the presence of 1-propanephosphonic acid cyclic anhydride (T3P (R)), rendering possible the highly efficient preparation of an alpha-amino amide library in medium to excellent yields. This study represents the first case in which T3P (R) has been used in the Ugi reaction. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：70 / 77
页数：8
相关论文
共 50 条
  • [31] T3P catalyzed one pot three-component synthesis of 2,3-disubstituted 3H-quinazolin-4-ones
    Raghavendra, Goravanahalli M.
    Kumar, Chottanahalli S. Pavan
    Suresha, Gejjalagere P.
    Rangappa, Kanchugarakoppal S.
    Mantelingu, Kempegowda
    CHINESE CHEMICAL LETTERS, 2015, 26 (08) : 963 - 968
  • [32] T3P catalyzed one pot three-component synthesis of 2,3-disubstituted 3H-quinazolin-4-ones
    Goravanahalli M.Raghavendra
    Chottanahalli S.Pavan Kumar
    Gejjalagere P.Suresha
    Kanchugarakoppal S.Rangappa
    Kempegowda Mantelingu
    Chinese Chemical Letters, 2015, 26 (08) : 963 - 968
  • [33] Copper-Catalyzed Synthesis of α-Amino Imides from Tertiary Amines: Ugi-Type Three-Component Assemblies Involving Direct Functionalization of sp3 C-Hs Adjacent to Nitrogen Atoms
    Ye, Xin
    Xie, Chunsong
    Pan, Yuanyuan
    Han, Laihong
    Xie, Tian
    ORGANIC LETTERS, 2010, 12 (19) : 4240 - 4243
  • [34] Propylphosphonic anhydride (T3P®): an efficient reagent for the one-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles
    Augustine, John Kallikat
    Vairaperumal, Veeramani
    Narasimhan, Sharmila
    Alagarsamy, Padma
    Radhakrishnan, Anbarasi
    TETRAHEDRON, 2009, 65 (48) : 9989 - 9996
  • [35] Selective synthesis of 5,6-dihydrophenanthridines, 5,6-dihydrobenzo[c][1,8]naphthyridines and their fully aromatized analogues via the Pictet-Spengler reaction mediated by peptide coupling agent propylphosphonic anhydride (T3P)
    Augustine, John Kallikat
    Bombrun, Agnes
    Alagarsamy, Padma
    Jothi, Anandh
    TETRAHEDRON LETTERS, 2012, 53 (46) : 6280 - 6287
  • [36] One-pot oxidative Ugi-type three-component reaction of aromatic hydrocarbons of petroleum naphtha: comparing catalytic effect of cellulose- and wool-SO3H supported with manganese dioxide nanostructures
    Shaabani, Ahmad
    Shaabani, Zeinab
    Badali, Elham
    RSC ADVANCES, 2015, 5 (112): : 91966 - 91973
  • [37] New four-component Ugi-type reaction.: Synthesis of 3-methyl-1-oxo-1,3,4,6,11,11a-hexahydro-2H-pyrazino[1,2-b]isoquinoline-3-carboxamides
    Ilyn, Alexey P.
    Trifilenkov, Andrey S.
    Kovrigin, Denis I.
    Yudin, Michail V.
    Ivachtchenko, Alexandre V.
    HETEROCYCLIC COMMUNICATIONS, 2006, 12 (02) : 107 - 110
  • [38] BrOnsted Acid/Rhodium(II) Cooperative Catalytic Asymmetric Three-Component Aldol-Type Reaction for the Synthesis of 3-Amino Oxindoles
    Ren, Lei
    Lian, Xiao-Lei
    Gong, Liu-Zhu
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (10) : 3315 - 3318
  • [39] Zwitterionic-Type Molten Salt: A Mild and Efficient Organocatalyst for the Synthesis of 3-Aminoalkylated Indoles via Three-Component Coupling Reaction
    Kundu, Dhiman
    Bagdi, Avik Kr
    Majee, Adinath
    Hajra, Alakananda
    SYNLETT, 2011, (08) : 1165 - 1167
  • [40] An Efficient, Regioselective, Versatile Synthesis of N-Fused 2-and 3-Aminoimidazoles via Ugi-Type Multicomponent Reaction Mediated by Zirconium(IV) Chloride in Polyethylene Glycol-400
    Guchhait, Sankar K.
    Madaan, Chetna
    SYNLETT, 2009, (04) : 628 - 632
12345