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
  • [1] Synthesis of some new derivatives of 2-methyl imidazole
    Ganguly, S
    Razdan, B
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 14 (03) : 253 - 254
  • [2] IMINOPHOSPHORANE-MEDIATED IMIDAZOLE RING FORMATION - A NEW AND GENERAL ENTRY TO APLYSINOPSIN-TYPE ALKALOIDS OF MARINE ORIGIN
    MOLINA, P
    ALMENDROS, P
    FRESNEDA, PM
    TETRAHEDRON, 1994, 50 (07) : 2241 - 2254
  • [3] Iminophosphorane-mediated synthesis of 1-acyl-beta-carbolines: A new access to the alkaloids eudistomin T, S and xestomanzamine A of marine origin
    Molina, P
    Fresneda, PM
    GarciaZafra, S
    TETRAHEDRON LETTERS, 1996, 37 (52) : 9353 - 9356
  • [4] Reduction of 2,5-bis(3′-indolyl)pyrazines to 2,5-bis(3′-indolyl)piperazines:: Synthesis of bisindolylpiperazine marine alkaloids dragmacidin A, B, and C
    Tonsiengsom, F
    Miyake, FY
    Yakushijin, K
    Horne, DA
    SYNTHESIS-STUTTGART, 2006, 1 (01): : 49 - 54
  • [5] Electrochemical synthesis of new derivatives of 2-(2′-furyl)benz-imidazole
    Aleksandrov, AA
    Galikyan, TG
    Elchaninov, MM
    Popova, OV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2001, (08): : 1131 - 1132
  • [6] SYNTHESIS OF NEW IMIDAZOLE DERIVATIVES AS POTENTIAL INHIBITORS OF THROMBOXANE SYNTHETASE .2.
    BANFI, A
    BENEDINI, F
    SALA, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (02) : 401 - 404
  • [7] NEW SYNTHESIS OF IMIDAZOLE DERIVATIVES .1. PREPARATION OF 2-SUBSTITUTED IMIDAZOLE-4-ALCOHOLS
    DZIURON, P
    SCHUNACK, W
    ARCHIV DER PHARMAZIE, 1973, 306 (05) : 347 - 350
  • [8] Synthesis of some new imidazole-2-thiols and their derivatives as potent antimicrobial agents
    Dhawas, Amol K.
    Thakare, Suresh S.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2014, 53 (05): : 642 - 646
  • [9] Studies on the synthesis of Strychnos indole alkaloids from 2-(3-indolyl)piperidine derivatives.: A new synthetic entry to the indolo[3,2-a]quinolizidine system
    Amat, M
    Llor, N
    Coll, MD
    Casamitjana, N
    Bosch, J
    ARKIVOC, 2004, : 14 - 25
  • [10] Nagelamide I and 2,2′-Didebromonagelamide B, New Dimeric Bromopyrrole-Imidazole Alkaloids from a Marine Sponge Agelas sp.
    Iwai, Takahiro
    Kubota, Takaaki
    Fromont, Jane
    Kobayashi, Jun'ichi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2014, 62 (02) : 213 - 216