SYNTHESIS OF 2-DIMETHYLAMINOIMIDAZOLE DERIVATIVES - A NEW ACCESS TO INDOLYL-IMIDAZOLE ALKALOIDS OF MARINE ORIGIN

被引:29
|
作者
DALKAFOUKI, A [1 ]
ARDISSON, J [1 ]
KUNESCH, N [1 ]
LACOMBE, L [1 ]
POISSON, JE [1 ]
机构
[1] COLL FRANCE,CNRS,CHIM INTERACT MOLEC LAB,F-75231 PARIS 05,FRANCE
关键词
INDOLYL-IMIDAZOLES; ALKALOIDS; APLYSINOPSIN; 2-DIMETHYLAMINOIMIDAZOLE; MARINE PRODUCTS;
D O I
10.1016/S0040-4039(00)92376-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first preparation of 2-dimethylaminoimidazole 1a, a structural feature of several marine products was undertaken and its reactivity investigated. The synthesis of natural alkaloids 5 and 12b was achieved by direct coupling of the easily accessible oxidized 2-dimethylaminoimidazoles 7 and 8 with indole-3-carboxaldehyde and indole respectively, demonstrating the usefulness of this approach for other structurally related natural products.
引用
收藏
页码:5325 / 5328
页数:4
相关论文
共 50 条
  • [21] Design, Synthesis, and Biological Evaluation of New 1H-Imidazole-2-Carboxylic Acid Derivatives as Metallo-β-Lactamase Inhibitors
    Li, Rong
    Su, Huilin
    Chen, Wei
    Yan, Yu-Hang
    Zhou, Cong
    Mou, Luohe
    Yang, Huan
    Qian, Shan
    Wang, Zhouyu
    Yang, Lingling
    Li, Guo-Bo
    BIOORGANIC & MEDICINAL CHEMISTRY, 2022, 72
  • [22] A New and Efficient Synthesis of Derivatives of Octahydro-4H-pyrrolo-[1,2-c]pyrido[1′,2′-a]imidazole
    Rouchaud, Anne
    Braekman, Jean-Claude
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (12) : 2346 - 2353
  • [23] Synthesis, Biological Evaluation, Molecular Docking and Kinetic Investigation of New 2,4,5-Trisubstituted Imidazole Derivatives as Antidiabetic Agents
    Kumar, Pawan
    Syal, Bindu
    Seboletswe, Pule
    Cele, Nosipho
    Olofinsan, Kolawole
    Singh, Parvesh
    Shahidul Islam, Md.
    Singh, Deepika
    Gupta, Princy
    CHEMISTRYSELECT, 2023, 8 (31):
  • [24] Access to newly functionalized imidazole derivatives: efficient synthesis of novel 5-amino-2-thioimidazoles using propylphosphonic anhydride (®T3P)
    Lasalle, Manuel
    Picon, Sylvain
    Boulahjar, Rajaa
    Hoguet, Vanessa
    Van Obbergen, Jolien
    Roussel, Pascal
    Deprez, Benoit
    Charton, Julie
    TETRAHEDRON LETTERS, 2015, 56 (08) : 1011 - 1014
  • [25] Direct access to marine pyrrole-2-aminoimidazoles, oroidin, and derivatives, via new acyl-1,2-dihydropyridin intermediates
    Schroif-Gregoire, Cosima
    Travert, Nathalie
    Zaparucha, Anne
    Al-Mourabit, Ali
    ORGANIC LETTERS, 2006, 8 (14) : 2961 - 2964
  • [26] Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide
    Ragno, Rino
    Coluccia, Antonio
    La Regina, Giuseppe
    De Martino, Gabriella
    Piscitelli, Francesco
    Lavecchia, Antonio
    Novellino, Ettore
    Bergamini, Alberto
    Ciaprini, Chiara
    Sinistro, Anna
    Maga, Giovanni
    Crespan, Emanuele
    Artico, Marino
    Silvestri, Romano
    JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (11) : 3172 - 3184
  • [27] SYNTHESIS OF NEW IMIDAZOLE 3-OXIDES; UNEXPECTED DEOXYGENATION OF SOME DERIVATIVES IN THE REACTION WITH 2,2,4,4-TETRAMETHYLCYCLOBUTANE-1,3-DITHIONE
    Mloston, Grzegorz
    Jasinski, Marcin
    Rygielska, Dorota
    Heimgartner, Heinz
    HETEROCYCLES, 2011, 83 (04) : 765 - 776
  • [28] Synthesis and antibacterial activity of some new imidazole, Imidazo[2,1-c] triazole and Imidazo[1,2-e] tetrazole derivatives
    Al-Tamamy, Hussein A.
    Fattah, M. E. Abdel
    ORIENTAL JOURNAL OF CHEMISTRY, 2010, 26 (02) : 421 - 427
  • [29] Synthesis and evaluation of anti-tubercular and antibacterial activities of new 4-(2,6-dichlorobenzyloxy)phenyl thiazole, oxazole and imidazole derivatives. Part 2
    Lu, Xiaoyun
    Liu, Xiaobo
    Wan, Baojie
    Franzblau, Scott G.
    Chen, Lili
    Zhou, Changlin
    You, Qidong
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 49 : 164 - 171
  • [30] New access to 1,3-dialkyl-2,3-dihydro-2-imino-1H-imidazoles and their application to the first total synthesis of naamine B, a marine 2,3-dihydro-2-imino-1,3-dimethyl-1H-imidazole alkaloid
    Kawasaki, I
    Nakamura, S
    Kakuno, A
    Yamashita, M
    Ohta, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (23): : 3095 - 3099