TFA-promoted (hetero)arylation/hydroxylation of quinoxaline-2-one derivatives with electron-rich aromatic compounds

被引:0
|
作者
Jatoth, Ramanna [1 ]
Gugulothu, Kishan [1 ]
Ravi, Nidhi [2 ]
Gayathri, Ranamalla [2 ]
Chandrakumar, Shravani Parehosahalli [2 ]
Kumar, K. Shiva [1 ,2 ]
机构
[1] Osmania Univ, Dept Chem, Hyderabad 500007, India
[2] Cent Univ Kerala, Sch Phys Sci, Dept Chem, Kasaragod 671320, Kerala, India
关键词
ONE-POT SYNTHESIS; DIARYLIODONIUM SALTS; ARYLATION; QUINOXALINONES; INDOLES;
D O I
10.1039/d4ob00882k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal- and solvent-free, one-pot and TFA-promoted method for the construction of hetero/aryl-substituted quinoxalin-2-ones, pyrazin-2(1H)-ones, and pyrimidin-4(3H)-ones is reported. This method involves the reaction of chloro-derivatives of nitrogen heterocycles with electron-rich arenes/heteroarenes, followed by hydroxylation. This protocol is easy to use, providing access to (hetero)aryl-substituted N-heterocycles in good yields.
引用
收藏
页码:313 / 317
页数:5
相关论文
共 12 条
  • [1] Lithium perchlorate assisted one-pot three-component aminoalkylation of electron-rich aromatic compounds
    Saidi, MR
    Azizi, N
    Naimi-Jamal, MR
    TETRAHEDRON LETTERS, 2001, 42 (45) : 8111 - 8113
  • [2] Lewis acid-promoted imine synthesis by the insertion of isocyanides into C-H bonds of electron-rich aromatic compounds
    Tobisu, Mamoru
    Yamaguchi, Seiji
    Chatani, Naoto
    ORGANIC LETTERS, 2007, 9 (17) : 3351 - 3354
  • [3] REACTIVITY OF 3,6-DIMETHOXY-3,6-DIMETHYLCYCLOHEXA-1,4-DIENE .2. REGIOSELECTIVE ARYLATION OF ELECTRON-RICH AROMATIC-COMPOUNDS
    ALONSO, F
    YUS, M
    TETRAHEDRON, 1991, 47 (02) : 313 - 316
  • [4] [Omim][BF4] ionic liquid, a green and recyclable medium for one-pot aminomethylation of electron-rich aromatic compounds
    Arzephoni, Amene Yaghoubi
    Naimi-Jamal, M. Reza
    Sharifi, Ali
    Abaee, M. Saeed
    Mirzaei, Mojtaba
    JOURNAL OF CHEMICAL RESEARCH, 2013, (04) : 216 - 218
  • [5] Palladium-Catalyzed Direct C2-Arylation of Benzo[b]thiophenes with Electron-Rich Aryl Halides: Facile Access to Thienoacene Derivatives
    Ichioka, Fumiki
    Itai, Yuhei
    Nishii, Yuji
    Miura, Masahiro
    SYNLETT, 2017, 28 (20) : 2812 - 2816
  • [6] HIGH-PRESSURE-PROMOTED (2 + 2) CYCLOADDITIONS OF IMINES WITH ELECTRON-RICH ALKENES - A SIMPLE ROUTE TO AZETIDINES AND BETA-AMINO CARBONYL-COMPOUNDS
    ABEN, RWM
    SMIT, R
    SCHEEREN, JW
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03): : 365 - 370
  • [7] Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride. Part 2: The Friedel-Crafts allylation and cyclopropylation of electron-rich aromatic compounds
    Kirihara, Masayuki
    Noguchi, Takuya
    Kakuda, Hiroko
    Akimoto, Tatsuhiro
    Shimajiri, Akihiro
    Morishita, Minori
    Hatano, Akihiko
    Hirai, Yoshiro
    TETRAHEDRON LETTERS, 2006, 47 (22) : 3777 - 3780
  • [8] PENTAATOMIC HETEROAROMATIC CATIONS .15. 2-SUBSTITUTED 1,3-BENZOXATHIOLIUM TETRAFLUOROBORATES AS USEFUL ACYLATING AGENTS OF ELECTRON-RICH AROMATIC AND HETEROAROMATIC-COMPOUNDS
    CADAMURO, S
    DEGANI, I
    FOCHI, R
    GATTI, A
    REGONDI, V
    SYNTHESIS-STUTTGART, 1987, (03): : 311 - 314
  • [9] Hetero-Diels-Alder reactions of perfluoroalkyl thioamides with electron-rich 1,3-dienes: synthesis of new 2-aminosubstituted-3,6-dihydro-2H-thiopyrans and related compounds
    Kanishchev, Oleksandr S.
    Sanselme, Morgane
    Bouillon, Jean-Philippe
    TETRAHEDRON, 2013, 69 (04) : 1322 - 1336
  • [10] Cycloaddition reaction of 2-azadienes derived from β-amino acids with electron-rich and electron-deficient alkenes and carbonyl compounds.: Synthesis of pyridine and 1,3-oxazine derivatives
    Palacios, F
    Herrán, E
    Rubiales, G
    Ezpeleta, JM
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07): : 2131 - 2135