Direct synthesis of nitroaryl acetylenes from acetylenes and nitroarenes via eoxidative nucleophilic substitution of hydrogen

被引：10
|
作者：
Bujok, Robert [1 ]
Makosza, Mieczyslaw [1 ]
机构：
[1] Polish Acad Sci, Inst Organ Chem, Ul Kasprzaka 44-52, PL-01224 Warsaw, Poland
来源：
CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 85期
关键词：
ORGANIC-ANIONS; EFFICIENT SYNTHESIS; DERIVATIVES; HETEROCYCLES; CYCLIZATION; CARBANIONS; AMINATION; INDOLES; ACCESS;
D O I：
10.1039/c6cc07475h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Acetylenic carbanions add to nitroarenes (dinitrobenzenes, nitropyridines, etc.) to form sigma(H)-adducts that are subsequently oxidized by DDQ according to the oxidative nucleophilic substitution of hydrogen (ONSH) pathway to give nitroaryl acetylenes.
引用
收藏
页码：12650 / 12652
页数：3
相关论文
共 50 条
  • [41] Synthesis of dithienoquinazolines from pyrimidines via intramolecular nucleophilic aromatic substitution of hydrogen
    Egor V. Verbitskiy
    Ekaterina M. Dinastiya
    Anna A. Baranova
    Oleg S. Eltsov
    Gennady L. Rusinov
    Oleg N. Chupakhin
    Valery N. Charushin
    Chemistry of Heterocyclic Compounds, 2017, 53 : 1156 - 1160
  • [42] Synthesis of dithienoquinazolines from pyrimidines via intramolecular nucleophilic aromatic substitution of hydrogen
    Verbitskiy, Egor V.
    Dinastiya, Ekaterina M.
    Baranova, Anna A.
    Eltsov, Oleg S.
    Rusinov, Gennady L.
    Chupakhin, Oleg N.
    Charushin, Valery N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (10) : 1156 - 1160
  • [43] NITROACETYLENES - SYNTHESIS OF 1-NITRO-2-(TRIALKYLSILYL)ACETYLENES VIA NITRODESILYLATION OF BIS(TRIALKYLSILYL)ACETYLENES
    SCHMITT, RJ
    BOTTARO, JC
    MALHOTRA, R
    BEDFORD, CD
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11): : 2294 - 2297
  • [44] Synthesis of 2,1-Benzisoxazoles by Nucleophilic Substitution of Hydrogen in Nitroarenes Activated by the Azole Ring
    Pokhodylo, Nazariy T.
    Teslenko, Yuriy O.
    Matiychuk, Vasyl S.
    Obushak, Mykola D.
    SYNTHESIS-STUTTGART, 2009, (16): : 2741 - 2748
  • [45] NOVEL SYNTHESIS OF ACETYLENES AND POLYENES VIA DESULFONYLATION REACTION
    MANDAI, T
    YANAGI, T
    ARAKI, K
    MORISAKI, Y
    KAWADA, M
    OTERA, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) : 3670 - 3672
  • [46] SYNTHESIS OF ARYL AND HETEROCYCLIC ACETYLENES VIA COPPER ACETYLIDES
    ATKINSON, RE
    CURTIS, RF
    JONES, DM
    TAYLOR, JA
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (16): : 2173 - +
  • [47] SYNTHESIS OF ARYL AND HETEROCYCLIC ACETYLENES VIA COPPER ACETYLIDES
    ATKINSON, RE
    CURTIS, RF
    JONES, DM
    TAYLOR, JA
    CHEMICAL COMMUNICATIONS, 1967, (14) : 718 - &
  • [48] The synthesis of (±)-aminoglutethimide via vicarious nucleophilic aromatic substitution of hydrogen
    Bushell, SM
    Crump, JP
    Lawrence, NJ
    Pineau, G
    TETRAHEDRON, 1998, 54 (10) : 2269 - 2274
  • [49] HETEROSUBSTITUTED ACETYLENES .30. A NEW MECHANISM OF NUCLEOPHILIC HALOGEN SUBSTITUTION AT ACETYLENE TRIPLE BONDS
    VIEHE, HG
    DELAVARE.SY
    CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (04): : 1216 - &
  • [50] Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen
    Zasada, Aleksandra
    Brzeskiewicz, Jakub
    Antoniak, Damian
    Bechcicka, Malgorzata
    Loska, Rafal
    Makosza, Mieczyslaw
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (05) : 994 - 999
12345