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
  • [21] A convenient synthesis of some new indeno[1,2-b]pyridines and indeno[1,2-b]thieno[3,2-e]pyridine derivatives with potential biological activity
    El-Ossaily, Yasser A.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (05) : 1109 - 1117
  • [22] An Eco-Friendly Stereoselective Synthesis of Novel Derivatives of Indeno[1,2-b]Pyrrole and Indeno[1,2-c]Pyridazine
    Gein, Vladimir L.
    Nosova, Natalia V.
    Yankin, Andrei N.
    Bazhina, Alina Y.
    Dmitriev, Maksim V.
    POLYCYCLIC AROMATIC COMPOUNDS, 2021, 41 (03) : 540 - 552
  • [23] Efficient synthesis of chiral isoquinoline and pyrido[1,2-b]isoquinoline derivatives via intramolecular Heck reactions
    Sánchez-Sancho, F
    Mann, E
    Herradón, B
    ADVANCED SYNTHESIS & CATALYSIS, 2001, 343 (04) : 360 - 368
  • [24] NOVEL PHTHALIDEISOQUINOLINE SYNTHESIS FROM BENZ[D]INDENO[1,2-B]AZEPINE
    KAMETANI, T
    HIRATA, S
    IHARA, M
    FUKUMOTO, K
    HETEROCYCLES, 1975, 3 (05) : 405 - 411
  • [25] One-Pot Strategy for the Synthesis of Indeno[1,2-b]Chromene Derivatives
    Sedighimehr, Iman
    Karami, Bahador
    Farahi, Mahnaz
    CHEMISTRY OF NATURAL COMPOUNDS, 2022, 58 (02) : 249 - 253
  • [26] Synthesis of Benzo[c]azocanones and Indeno[1,2-b]pyrroles from Oxoindanecarboxylates
    Behler, Florian
    Habecker, Florian
    Saak, Wolfgang
    Kluener, Thorsten
    Christoffers, Jens
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (22) : 4231 - 4240
  • [27] One-Pot Strategy for the Synthesis of Indeno[1,2-b]Chromene Derivatives
    Iman Sedighimehr
    Bahador Karami
    Mahnaz Farahi
    Chemistry of Natural Compounds, 2022, 58 : 249 - 253
  • [28] SYNTHESIS AND SUBSTITUTION REACTIONS OF ACENAPHTHO (1,2-B)THIOPHENE AND 1-METHYLACENAPHTHO(1,2-B)PYRROLE
    HAUPTMANN, S
    SCHOLZ, M
    KOHLER, HJ
    HOFMANN, HJ
    JOURNAL FUR PRAKTISCHE CHEMIE-PRACTICAL APPLICATIONS AND APPLIED CHEMISTRY, 1969, 311 (04): : 614 - +
  • [29] Convenient two-step one-pot synthesis of 3-substituted imidazo[1,2-a]pyridines and imidazo[1,2-b]pyridazines
    Hongli Fan
    Fenghai Li
    Journal of Chemical Sciences, 2018, 130
  • [30] Convenient two-step one-pot synthesis of 3-substituted imidazo[1,2-a]pyridines and imidazo[1,2-b]pyridazines
    Fan, Hongli
    Li, Fenghai
    JOURNAL OF CHEMICAL SCIENCES, 2018, 130 (05)