Two-step synthesis of indeno[1,2-b]furazanopyrazines through combination of the SNH and Heck reactions

被引:1
|
作者
Kvashnin, Yuriy A. [1 ,2 ]
Belyaev, Danila V. [1 ,3 ]
Kodess, Mikhail I. [1 ]
Ezhikova, Marina A. [1 ]
Rusinov, Gennady L. [1 ,2 ]
Verbitskiy, Egor V. [1 ,2 ]
Charushin, Valery N. [1 ,2 ]
机构
[1] Russian Acad Sci, Ural Branch, IYa Postovsky Inst Organ Synth, Ekaterinburg 620137, Russia
[2] Ural Fed Univ, Inst Chem Engn, Ekaterinburg 620002, Russia
[3] Natl Med Res Ctr Phthisiopulmonol & Infect Dis, Ural Res Inst Phthisiopulmonol, Ekaterinburg 620039, Russia
关键词
furazanopyrazines; 1; 2; 5]oxadiazolo[3; 4-b]pyrazines; intramolecular Heck reaction; C-H functionalization; SNH reactions; antimycobacterials; indeno[1; 2-b][1; 4-e]pyrazines; DERIVATIVES; SYSTEMS;
D O I
10.1016/j.mencom.2023.10.004
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enamines generated in situ from aliphatic amines and acetone react with 5-(2-bromophenyl)furazano[3,4-b]pyrazines via the nucleophilic substitution of hydrogen atom of the pyrazine ring. A representative of 9H-indeno[1,2-b]furazanopyrazin-9-ylidene ring system has been accessed by exploiting the intramolecular Heck cyclization of the obtained SNH-product. Several compounds derived from furazano[3,4-b]pyrazin-5-yl]prop-1-en-2-amines, proved to exhibit a bacteriostatic activity in vitro against Mycobacterium tuberculosis H37Rv.
引用
收藏
页码:753 / 755
页数:3
相关论文
共 50 条
  • [31] Synthesis of cyclopropa[c]indeno[1,2-b]quinolines through a MCR/Staudinger/aza-Wittig sequence
    Nie, Bing-Jie
    Wu, Li-Hui
    Hu, Ruo-Fei
    Sun, Yang
    Wu, Jing
    He, Ping
    Huang, Nian-Yu
    SYNTHETIC COMMUNICATIONS, 2017, 47 (15) : 1368 - 1374
  • [32] Synthesis of Indeno[1,2-b]indole Derivatives through One-Pot Sequential or Two-Step Iodine-Catalyzed C-O Activation and Palladium-Catalyzed C-H Functionalization
    Xu, Hai-Yan
    Xu, Xiao-Ping
    Wang, Shun-Yi
    Ji, Shun-Jun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (28) : 5440 - 5445
  • [33] SYNTHESIS OF INDENO[1,2-B]PYRAZINE N-OXIDES BY REACTION OF NINHYDRIN WITH 1,2-BISHYDROXYLAMINES
    MAZHUKIN, DG
    TIKHONOV, AY
    VOLODARSKY, LB
    EVLAMPIEVA, NP
    VETCHINOV, VP
    MAMATYUK, VI
    LIEBIGS ANNALEN DER CHEMIE, 1994, (10): : 983 - 987
  • [34] Three-Component Domino Reactions for Selective Formation of Indeno[1,2-b]indole Derivatives
    Jiang, Bo
    Li, Qiu-Yun
    Tu, Shu-Jiang
    Li, Guigen
    ORGANIC LETTERS, 2012, 14 (20) : 5210 - 5213
  • [35] Synthesis of Indeno[1,2-b]benzofurans using TPAB as Highly Efficient and Recoverable Catalyst
    Marjani, Ahmad Poursattar
    Khalafy, Jabbar
    Akbarzadeh, Somayeh
    SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2019, 72 : 160 - +
  • [36] Convenient Synthesis Of New Indeno[1,2-b]Pyridine Derivatives For Antimicrobial And Antioxidant Evaluation
    Kotb, E. R.
    Soliman, H. A.
    El-Dein, E. M. H. Morsy A. Negm
    EGYPTIAN JOURNAL OF CHEMISTRY, 2021, 64 (03): : 1503 - 1514
  • [37] Synthesis of some novel indeno[1,2-b]quinoxalin spiro-β-lactam conjugates
    Rad, Javad Ameri
    Jarrahpour, Aliasghar
    Ersanli, Cem Cuneyt
    Atioglu, Zeliha
    Akkurt, Mehmet
    Turos, Edward
    TETRAHEDRON, 2017, 73 (08) : 1135 - 1142
  • [38] Synthesis of 11H-Indeno[1,2-b]quinolines via the Friedhinder reaction
    Xu, F
    Yang, DQ
    Jiang, KL
    Guo, W
    CHINESE CHEMICAL LETTERS, 2006, 17 (02) : 187 - 190
  • [39] Environmentally Benign Synthesis of Indeno[1,2-b]quinolines via an Intramolecular Povarov Reaction
    Chen, Ming
    Sun, Ning
    Liu, Yuanhong
    ORGANIC LETTERS, 2013, 15 (21) : 5574 - 5577
  • [40] Recent advancement in the synthesis of diverse spiro-indeno[1,2-b]quinoxalines: a review
    Singh, Ruby
    Bhardwaj, Diksha
    Saini, Munna Ram
    RSC ADVANCES, 2021, 11 (08) : 4760 - 4804