Microwave-assisted synthesis of α-aminophosphine oxides by the Kabachnik-Fields reaction applying amides as the starting materials

被引:10
|
作者
Tripolszky, Anna [1 ]
Zoboki, Lili [1 ]
Balint, Erika [1 ]
Koti, Janos [2 ]
Keglevich, Gyorgy [1 ]
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary
[2] Gedeon Richter Plc, Budapest, Hungary
关键词
alpha-Aminophosphine oxides; carboxylic acid amides; Kabachnik-Fields reaction; microwave; AMINO PHOSPHONATES; SOLVENT-FREE; IONIC LIQUID; EFFICIENT; CATALYST; INHIBITORS; BIS; CONVENIENT; FACILE; ROUTE;
D O I
10.1080/00397911.2019.1584675
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of acylated alpha-aminophosphine oxides were synthesized by the microwave-assisted Kabachnik-Fields reaction of a series of carboxylic acid amides, formaldehyde and secondary phosphine oxides. To compensate the lower reactivity of the -NH2 reagents, they had to be used in an excess. The solvolytic condensations furnished the alpha-aminophosphine oxides in yields of 58-93% after purification by chromatography.
引用
收藏
页码:1047 / 1054
页数:8
相关论文
共 50 条
  • [31] Camphor-derived thioureas: Synthesis and application in asymmetric Kabachnik-Fields reaction
    Reddy, Pogula Sreekanth
    Reddy, Motakatla Venkata Krishna
    Reddy, Peddiahgari Vasu Govardhana
    CHINESE CHEMICAL LETTERS, 2016, 27 (06) : 943 - 947
  • [32] First synthesis of α-aminophosphonates from natural porphyrin derivatives by the Kabachnik-Fields reaction
    Kabachnic, MM
    Zobnina, EV
    Pavlov, VV
    Konstantinov, IO
    Ponomarev, GV
    Beletskaya, IP
    RUSSIAN CHEMICAL BULLETIN, 2005, 54 (01) : 262 - 265
  • [33] Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik-Fields Condensation
    Tajti, Adam
    Toth, Nora
    Ravai, Bettina
    Csontos, Istvan
    Szabo, Pal Tamas
    Balint, Erika
    MOLECULES, 2020, 25 (14):
  • [34] Synthesis of covalent organic frameworks via Kabachnik-Fields reaction for water treatment
    Wu, Wen-Xiu
    Li, Fei
    Yao, Bing-Jian
    Ding, Luo-Gang
    Kan, Jing-Lan
    Liu, Fei
    Zhao, Guo-Yan
    Wang, Song
    Dong, Yu-Bin
    JOURNAL OF HAZARDOUS MATERIALS, 2022, 433
  • [35] Camphor-derived thioureas: Synthesis and application in asymmetric Kabachnik-Fields reaction
    Pogula Sreekanth Reddy
    Motakatla Venkata Krishna Reddy
    Peddiahgari Vasu Govardhana Reddy
    Chinese Chemical Letters, 2016, 27 (06) : 943 - 947
  • [36] T3P®-promoted Kabachnik-Fields reaction: an efficient synthesis of α-aminophosphonates
    Milen, Matyas
    Abranyi-Balogh, Peter
    Dancso, Andras
    Frigyes, David
    Pongo, Laszlo
    Keglevich, Gyoergy
    TETRAHEDRON LETTERS, 2013, 54 (40) : 5430 - 5433
  • [37] An ultra-sound assisted synthesis of α-aminophosphonates from benzyl halides via sequential Kornblum and Kabachnik-fields reaction
    Amin, Rabia
    Ara, Tabassum
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2023, 198 (05) : 417 - 423
  • [38] Microwave-assisted synthesis of tetrazolyl pyrazole amides
    Hu, Jun
    Wang, Jikui
    Zhou, Taoyu
    Xu, Yanhua
    JOURNAL OF CHEMICAL RESEARCH, 2011, (09) : 525 - 527
  • [39] Facile Synthesis of α-Amino Phosphonates in Water by Kabachnik-Fields Reaction Using Magnesium Dodecyl Sulfate
    Ando, Kaori
    Egami, Tomoe
    HETEROATOM CHEMISTRY, 2011, 22 (3-4) : 358 - 362
  • [40] The Kabachnik-Fields Reaction in the Synthesis of Polyaminophosphonate Derivatives of p-tert-Butylthiacalix[4]arene
    Shibaeva, K. S.
    Mostovaya, O. A.
    Nazarova, A. A.
    Shurpik, D. N.
    Shiabiev, I. E.
    Kuznetsova, D. I.
    Stoykov, I. I.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (09) : 1812 - 1817