Synthesis of Pyrrolo[2,3-b]indole via Iodine(III)-Mediated Intramolecular Annulation

被引:53
|
作者
Tu, Dandan [1 ,2 ]
Ma, Liying [1 ]
Tong, Xiaogang [1 ,2 ]
Deng, Xu [1 ]
Xia, Chengfeng [1 ]
机构
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650201, Peoples R China
[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
HISTONE METHYLTRANSFERASE; CHEMISTRY; INHIBITOR; REVERSAL;
D O I
10.1021/ol302158h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New synthetic procedures for the pyrrolo[2,3-b]indole skeleton have been developed via intramolecular annulation of indole derivatives under iodine(III). A series of indole derivatives with different protecting groups or substitutions were explored to facilitate the corresponding pyrrolo[2,3-b]indole compounds in excellent yields.
引用
收藏
页码:4830 / 4833
页数:4
相关论文
共 50 条
  • [21] HYDROGENATED PYRROLO[2,3-B]PYRIDINES
    MOHRLE, H
    SPECKS, F
    ARCHIV DER PHARMAZIE, 1976, 309 (02) : 120 - 127
  • [22] THE SYNTHESIS OF SUBSTITUTED 2,3-DIHYDROTHIENO[2,3-B]THIOPHENES VIA INTRAMOLECULAR MICHAEL ADDITION
    WILLIAMS, TM
    HUDCOSKY, RJ
    HUNT, CA
    SHEPARD, KL
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (01) : 13 - 16
  • [23] A rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo[2,3-b]indole skeleton, a building block for 10b-hydroxy-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-diones
    Ley, SV
    Cleator, E
    Hewitt, PR
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (20) : 3492 - 3494
  • [24] SYNTHESIS OF BENZAZEPINES AND THEIR REARRANGEMENT INTO QUINOLINES AND PYRROLO(2,3-B)QUINOLINES
    VOGEL, A
    TROXLER, F
    LINDENMANN, A
    HELVETICA CHIMICA ACTA, 1969, 52 (07) : 1929 - +
  • [25] Robustanoids A and B, two novel pyrrolo[2,3-b] indole alkaloids from Coffea canephora: isolation and total synthesis
    Han, Jianxin
    Niu, Sheng-Tong
    Liu, Yushuang
    Gan, Lishe
    Wang, Tianfu
    Lu, Chong-Dao
    Yuan, Tao
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (04): : 586 - 589
  • [26] SYNTHESIS OF ANNELATED NADH MODELS IN BENZOTHIENO[2,3-B]PYRIDINE AND PYRIDO[2,3-B]INDOLE SERIES
    LEVACHER, V
    BOUSSAD, N
    DUPAS, G
    BOURGUIGNON, J
    QUEGUINER, G
    TETRAHEDRON, 1992, 48 (05) : 831 - 840
  • [27] FORMATION OF CERTAIN SUBSTITUTED 5H-PYRROLO[2,3-B]PYRAZINES BY THERMAL CYCLIZATION OF PYRAZINYLHYDRAZONES AND A ROUTE TO 5H-PYRAZINO[2,3-B]INDOLE - SYNTHESIS OF 5H-PYRROLO[2,3-B]PYRAZINE AND SOME OF ITS PROPERTIES
    CLARK, BAJ
    PARRICK, J
    DORGAN, RJJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (13): : 1361 - 1363
  • [28] ANNULATION OF PYRIDINE TO INDOLE BY A TANDEM AZA-WITTIG ELECTROCYCLIZATION STRATEGY - SYNTHESIS OF PYRIDO[2,3-B]INDOLES
    MOLINA, P
    FRESNEDA, PM
    SYNTHESIS-STUTTGART, 1989, (11): : 878 - 880
  • [29] Synthesis of Highly Fused Pyrano[2,3-b]pyridines via Rh(III)- Catalyzed C-H Activation and Intramolecular Cascade Annulation under Room Temperature
    Han, Xu
    Gao, Feng
    Li, Chunpu
    Fang, Daqing
    Xie, Xiong
    Zhou, Yu
    Liu, Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (10): : 6281 - 6294
  • [30] Synthesis of Unexpected Pyrrolo[2,3-b]quinoxaline-2-carbaldehydes via Sonogashira Coupling Reaction
    Keivanloo, Ali
    Bakherad, Mohammad
    Rahimi, Amin
    SYNTHESIS-STUTTGART, 2010, (10): : 1599 - 1602