Palladium catalyzed synthesis of sugar-fused indolines via C(sp2)-H/N-H activation

被引：7
|
作者：
Verma, Ashish Kumar [1 ]
Chennaiah, Ande [1 ]
Dubbu, Sateesh [1 ]
Vankar, Yashwant D. [1 ]
机构：
[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
CARBOHYDRATE RESEARCH | 2019年 / 473卷
关键词：
C(sp(2))-H/N-H activation in carbohydrates; Annulated sugars; Sugar-fused indolines; Sugar-fused indoles; C-H ACTIVATION; PD(II)-CATALYZED AMINATION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; C(SP(3))-H BONDS; NATURAL-PRODUCTS; CELL-ADHESION; ISOCHROMANS; ACCESS;
D O I：
10.1016/j.carres.2018.12.015
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A simple Pd(OAc)(2) catalyzed strategy for the synthesis of sugar-fused indolines from 2-N-oxalylamido-2-deoxy-C-aryl glycosides is reported by utilizing N-oxalylamido group as an auxiliary via C(sp(2))-H/N-H Activation. The reaction is successfully applied on glucose as well as galactose derived differently substituted 2-N-oxalylamido-2-deoxy-C-aryl glycosides to give sugar-fused indolines in moderate to good yields. The utility of this strategy in the synthesis of sugar-fused indoles is also described.
引用
收藏
页码：57 / 65
页数：9
相关论文
共 50 条
  • [1] Synthesis of Fused 1-Aminoindole Polycycles by a Sequence of Palladium-Catalyzed N-H and C(sp2)-H Arylations
    Thi Thanh Huyen Luong
    Brion, Jean-Daniel
    Alami, Mouad
    Messaoudi, Samir
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02): : 751 - 761
  • [2] Palladium-NHC Catalyzed Enantioselective Synthesis of Fused Indolines via Inert C(sp3)-H Activation
    Nakanishi, Masafumi
    Katayev, Dmitry
    Besnard, Celine
    Kuendig, E. Peter
    CHIMIA, 2012, 66 (04) : 241 - 243
  • [3] Allene C(sp2)-H Activation and Alkenylation Catalyzed by Palladium
    Schreib, Benedikt S.
    Son, Mina
    Aouane, Francoise A.
    Baik, Mu-Hyun
    Carreira, Erick M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (51) : 21705 - 21712
  • [4] Palladium(II)-Catalyzed Cycloamidination via C(sp2)-H Activation and Isocyanide Insertion
    Wang, Yong
    Zhu, Qiang
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (10) : 1902 - 1908
  • [5] Efficient palladium-catalyzed C(sp2)-H activation towards the synthesis of fluorenes
    Song, Juan
    Li, Yali
    Sun, Wei
    Yi, Chenglong
    Wu, Hao
    Wang, Haotian
    Ding, Keran
    Xiao, Kang
    Liu, Chao
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (11) : 9030 - 9033
  • [6] Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C-H activation
    Rago, Alexander J.
    Dong, Guangbin
    GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (02): : 216 - 227
  • [7] Palladium-Catalyzed Synthesis of Fluorenes by Intramolecular C(sp2)-H Activation at Room Temperature
    Tanji, Yutaka
    Tsuji, Yasushi
    Fujihara, Tetsuaki
    SYNLETT, 2020, 31 (08) : 805 - 808
  • [8] Highly Efficient Syntheses of Azetidines, Pyrrolidines, and Indolines via Palladium Catalyzed Intramolecular Amination of C(sp3)-H and C(sp2)-H Bonds at γ and δ Positions
    He, Gang
    Zhao, Yingsheng
    Zhang, Shuyu
    Lu, Chengxi
    Chen, Gong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) : 3 - 6
  • [9] Synthesis of Unsymmetrically Substituted Tetraphenylenes through Palladium-Catalyzed C(sp2)-H Activation
    Wan, Bin
    Zhang, Yanghui
    SYNTHESIS-STUTTGART, 2021, 53 (18): : 3299 - 3306
  • [10] Direct synthesis of 8-acylated quinoline N-oxides via palladium-catalyzed selective C-H activation and C(sp2)-C(sp2) cleavage
    Li, Guang-Hui
    Dong, Dao-Qing
    Yu, Xian-Yong
    Wang, Zu-Li
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (04) : 1667 - 1670
12345