Synthesis and nucleophilic dearomatization of highly electrophilic [1,2,5]selenadiazolo[3,4-b]pyridines

被引：0
|
作者：
V. V. Ivanova
A. K. Fedorenko
A. M. Starosotnikov
M. A. Bastrakov
机构：
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
来源：
Russian Chemical Bulletin | 2022年 / 71卷
关键词：
fused pyridines; C-nucleophiles; nucleophilic addition; 1,4-dihydropyridines; dearomatization; [1,2,5]selenadiazoles;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A number of [1,2,5]selenadiazolo[3,4-b]pyridines were synthesized on the basis of readily available 5-R-2,3-diaminopyridines. It was found that these compounds can be involved into the reactions with C-nucleophiles (1,3-dicarbonyl compounds, indoles) under mild conditions, in some cases with no base required. As a result, stable products of nucleophilic addition to the pyridine ring, 1,4-dihydropyridines fused with selenadiazole ring, were formed in up to 94% yield.
引用
收藏
页码：1826 / 1829
页数：3
相关论文
共 50 条
  • [1] Synthesis and nucleophilic dearomatization of highly electrophilic [1,2,5]selenadiazolo[3,4-b]pyridines
    Ivanova, V. V.
    Fedorenko, A. K.
    Starosotnikov, A. M.
    Bastrakov, M. A.
    RUSSIAN CHEMICAL BULLETIN, 2022, 71 (08) : 1826 - 1829
  • [2] Synthesis and reactivity of [1,2,5]thiadiazolo[3,4-b]pyridines and [1,2,5]selenadiazolo[3,4-b]pyridines (microreview)
    Bastrakov, Maxim A.
    Ivanova, Victoria V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2024, 60 (1-2) : 38 - 40
  • [3] [1,2,5]Selenadiazolo[3,4-b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions
    Konstantinova, Lidia S.
    Bobkova, Irina E.
    Nelyubina, Yulia V.
    Chulanova, Elena A.
    Irtegova, Irina G.
    Vasilieva, Nadezhda V.
    Camacho, Paula S.
    Ashbrook, Sharon E.
    Hua, Guoxiong
    Slawin, Alexandra M. Z.
    Woollins, J. Derek
    Zibarev, Andrey V.
    Rakitin, Oleg A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (25) : 5585 - 5593
  • [4] [1,2,5]Selenadiazolo[3,4-c][1,2,5]thiadiazole and [1,2,5]Selenadiazolo[3,4-c][1,2,5jthiadiazolidyl -: A synthetic, structural, and theoretical study
    Bagryanskaya, Irina Yu.
    Gatilov, Yuri V.
    Gritsan, Nina P.
    Ikorskii, Vladimir N.
    Irtegova, Irina G.
    Lonchakov, Anton V.
    Lork, Enno
    Mews, Ruediger
    Ovcharenko, Victor I.
    Semenov, Nikolay A.
    Vasilieva, Nadezhda V.
    Zibarev, Andrey V.
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2007, 30 (30) : 4751 - 4761
  • [5] Pyrazolo[3,4-b]pyridine in heterocyclic synthesis:: synthesis of new pyrazolo[3,4-b]pyridines, imidazo[1′,2′:1,5]pyrazolo[3,4-b]pyridines, and pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines
    Gad-Elkareem, Mohamed A. M.
    Abdel-Fattah, Azza M.
    Elneairy, Mohamed A. A.
    CANADIAN JOURNAL OF CHEMISTRY, 2007, 85 (09) : 592 - 599
  • [6] CHEMISTRY OF 1,2,5-THIADIAZOLES .5. SYNTHESIS OF 3,4-DIAMINO-1,2,5-THIADIAZOLE AND [1,2,5]THIADIAZOLO[3,4-B]PYRAZINES
    KOMIN, AP
    CARMACK, M
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (01) : 13 - 22
  • [7] Synthesis of pyrazolo[3,4-b]pyridines
    Lloyd, AW
    DRUG DISCOVERY TODAY, 1996, 1 (09) : 400 - 400
  • [8] A simple synthesis of 1Н-pyrazolo[3,4-b]pyridines
    Ekaterina E. Sizova
    Evgenii V. Arshinov
    Yana A. Kotsareva
    Larisa V. Glizdinskaya
    Galina P. Sagitullina
    Chemistry of Heterocyclic Compounds, 2017, 53 : 1026 - 1032
  • [9] CONDENSED HETEROCYCLES .13. SYNTHESIS OF "[1,2,5]THIADIAZOLO[3,4-C]QUINOLINES AND [1,2,5]SELENADIAZOLO[3,4-C]QUINOLINES
    SHARMA, KS
    SINGH, RP
    KUMARI, S
    SYNTHESIS-STUTTGART, 1983, (07): : 581 - 581
  • [10] A facile synthesis of substituted pyridines and pyrazolo[3,4-b]pyridines
    Kidwai, M
    Thakur, R
    Saxena, S
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (06) : 1181 - 1183
12345