Simultaneous formation of 3-(benzimidazol-2-yl)quinoxalin-2(1H)-ones and 2-(benzimidazol-2-yl)quinoxalines from quinoxalin-2(1H)-one-3-carbaldoximes when exposed to 1,2-benzenediamines

被引：3
|
作者：
Mamedov, Vakhid A. [1 ]
Zhukova, Nataliya A. [1 ]
Syakaev, Victor V. [1 ]
Gubaidullin, Aidar T. [1 ]
Kadyrova, Milyausha S. [1 ]
Beschastnova, Tat'yana N. [1 ]
Rizvanov, Il'dar Kh [1 ]
Latypov, Shamil K. [1 ]
机构：
[1] Russian Acad Sci, AE Arbuzov Inst Organ & Phys Chem, FRC Kazan Sci Ctr, Arbuzov Str 8, Kazan 420088, Russia
来源：
TETRAHEDRON | 2020年 / 76卷 / 52期
基金：
俄罗斯科学基金会;
关键词：
Weidenhagen reaction; Mamedov rearrangement; Quinoxalin-2(1H)-one-3-carbaldoximes; 1,2-Benzenediamines; Benzimidazol-2-ylquinoxalin(on)es;
D O I：
10.1016/j.tet.2020.131721
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Interaction of quinoxalin-2(1H)-one-3-carbaldoximes with 1,2-benzenediamine derivatives in AcOH or n-BuOH at reflux in the presence of sulfuric acid as catalyst was found to give 3-(benzimidazol-2-yl)quinoxalin-2(1H)-ones and 2-(benzimidazol-2-yl)quinoxalines in relatively good yields, which formed as a result of the Weidenhagen reaction and Mamedov rearrangement, respectively. The reaction in AcOH afforded 2-(benzimidazol-2-yl)quinoxalines in preference to the 3-(benzimidazol-2-yl)quinoxalin-2(1H)-ones, while the reverse result was obtained in n-BuOH. The synthetic utility of this strategy was illustrated by the concise, one-pot synthesis of 3-(3H-imidazo[4,5-b]pyridin-2-yl)quinoxalin-2(1H)-ones. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：12
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