Synthesis of a pyrrolo[1,4]benzodiazepinequinone

被引：8
|
作者：
Tapia, RA [1 ]
Centella, CR [1 ]
Valderrama, JA [1 ]
机构：
[1] Pontificia Univ Catolica Chile, Fac Quim, Santiago 22, Chile
来源：
SYNTHETIC COMMUNICATIONS | 1999年 / 29卷 / 12期
关键词：
D O I：
10.1080/00397919908086212
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Condensation of 3,6-dimethoxy-2-nitrobenzoyl chloride with L-proline methyl ester afforded amide 4, which underwent reductive cyclization with iron(II) sulfate and ammonium hydroxide to yield pyrrolobenzodiazepine 5. Oxidation of 5 with ammonium cerium(IV) nitrate led to the new heterocyclic quinone 6 in 53% overall yield.
引用
收藏
页码：2163 / 2168
页数：6
相关论文
共 50 条
  • [41] A SYNTHETIC METHOD FOR PYRROLO[1,4]-BENZODIAZEPINE ANTITUMOR ANTIBIOTICS
    KANEKO, T
    WONG, H
    DOYLE, TW
    HETEROCYCLES, 1984, 21 : 434 - 434
  • [42] PYRROLO[1,2-A][1,4] BENZODIAZEPINES - AN ORIGINAL 3-STEP SYNTHESIS FROM ANTHRANILONITRILE
    RAULT, I
    RAULT, S
    ROBBA, M
    TETRAHEDRON LETTERS, 1993, 34 (12) : 1929 - 1930
  • [43] SYNTHESIS AND REACTIONS OF PYRROLO[2,4-C][1,2,4]BENZOTRIAZINE AND 4-OXO-4H-PYRROLO[2,4-C][1,4]BENZOXAZINE
    CHEESEMAN, GW
    RAFIQ, M
    ROY, PD
    TURNER, CJ
    BOYD, GV
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (10): : 2018 - +
  • [44] Synthesis of DNA-Interactive Pyrrolo[2,1-c][1,4]benzodiazepines (PBDs)
    Antonow, Dyeison
    Thurston, David E.
    CHEMICAL REVIEWS, 2011, 111 (04) : 2815 - 2864
  • [45] PYRROLO[2,1-C][1,4]BENZODIAZEPINES - SYNTHESIS OF N-SUBSTITUTED AMIDINES
    FOLOPPE, MP
    RAULT, I
    RAULT, S
    ROBBA, M
    HETEROCYCLES, 1993, 36 (01) : 63 - 69
  • [46] Synthesis and biological activity of fused tetracyclic Pyrrolo[2,1-c][1,4] benzodiazepines
    Annor-Gyamfi, Joel K.
    Jarrett, John M.
    Osazee, Joseph O.
    Bialonska, Dobrusia
    Whitted, Crystal
    Palau, Victoria E.
    Shilabin, Abbas G.
    HELIYON, 2018, 4 (02):
  • [47] SYNTHESIS AND CHARACTERIZATION OF PYRROLO[2,1-C][1,4]BENZODIAZEPINE-CIRCUMDATIN CONJUGATES
    Srinivas, B.
    Devi, N. Saritha
    Sreenivasulu, G. K.
    Parameshwar, R.
    HETEROCYCLIC LETTERS, 2015, 5 (03): : 459 - 466
  • [48] Synthesis of new pyrrolo[2,1-b]quinazolinones by original rearrangement of pyrrolo [2,1-c][1,4]benzodiazepines
    Jolivet-Fouchet, S.
    Fabis, F.
    Bovy, P.
    Ochsenbein, P.
    Tetrahedron Letters, 39 (08):
  • [49] First Synthesis of 4H-Furo[3,2-f]pyrrolo[1,2-a] [1,4]diazepines
    Feng, X.
    Lancelot, J.-C.
    Prunier, H.
    Rault, S.
    Journal of Heterocyclic Chemistry, 1996, 33 (06)
  • [50] Annelated Pyrrolo[1,2-a][1,4]diazepines in Mannich Reaction
    Stroganova, Tatyana A.
    Red'kin, Viktor M.
    Vasilin, Vladimir K.
    Krapivin, Gennady D.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (04) : 854 - 858
12345