I2/NaH/DMF as oxidant trio for the synthesis of tryptanthrin from indigo or isatin

被引:12
|
作者
Brandao, Pedro [1 ,2 ,3 ]
Pinheiro, Daniela [1 ,2 ]
Sergio Seixas de Melo, J. [1 ,2 ]
Pineiro, Marta [1 ,2 ]
机构
[1] Univ Coimbra, CQC, Rua Larga, P-3004535 Coimbra, Portugal
[2] Univ Coimbra, Dept Chem, Rua Larga, P-3004535 Coimbra, Portugal
[3] Univ Evora, Inst Res & Adv Studies, Ctr Quim Evora, Rua Romao Ramalho, P-7000 Evora, Portugal
关键词
Tryptanthrin; DMF; Oxidation; Isatin; Indigo; OXIDATION; N; N-DIMETHYLFORMAMIDE; DERIVATIVES;
D O I
10.1016/j.dyepig.2019.107935
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Tryptanthrin, a product present in several natural sources used as colorants and very relevant in the field of Medicinal Chemistry, was synthesized from indigo and isatin under mild conditions using microwave irradiation. A plausible mechanism for the synthesis of tryptanthrin using the oxidant system formed by iodine, sodium hydride and DMF, the latter acting with dual activity as solvent and as the oxygen source, is proposed.
引用
收藏
页数:4
相关论文
共 50 条
  • [31] ALKESTIS INSCRIPTION FROM ODESSOS - IGBR I2 222
    CALDER, WM
    AMERICAN JOURNAL OF ARCHAEOLOGY, 1975, 79 (01) : 80 - 83
  • [32] Identification of an I2 binding protein from rabbit brain
    Kimura, A
    Tyacke, RJ
    Minchin, MCW
    Nutt, DJ
    Hudson, AL
    AGMATINE AND IMIDAZOLINES: THEIR NOVEL RECEPTORS AND ENZYMES, 2003, 1009 : 364 - 366
  • [33] Pd-Catalyzed Homo Cross-Dehydrogenative Coupling of 2-Arylpyridines by Using I2 as the Sole Oxidant
    Liu, Wenbo
    Zhu, Youquan
    Li, Chao-Jun
    SYNTHESIS-STUTTGART, 2016, 48 (11): : 1616 - 1621
  • [34] Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands
    Anastassiadou, M
    Danoun, S
    Crane, L
    Baziard-Mouysset, G
    Payard, M
    Caignard, DH
    Rettori, MC
    Renard, P
    BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (03) : 585 - 592
  • [35] I2 or I2/PIFA one-pot induced system for rapid synthesis of chalcogenated enamides, uracils or 2-pyridones under mild conditions
    Sanaa, Hamdi
    Dondasse, Ismael
    Retailleau, Pascal
    Nicolas, Cyril
    Gillaizeau, Isabelle
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (28) : 12793 - 12799
  • [36] I2 mediated one-pot synthesis of 1,2,4-triazoles from amidines and imidates
    Inturi, Surendra Babu
    Kalita, Biswajit
    Ahamed, A. Jafar
    TETRAHEDRON LETTERS, 2016, 57 (21) : 2227 - 2230
  • [37] Synthesis, characterisation and structural investigations of iodine-doped indium(III) and zirconium(IV) diphthalocyanines:: [InPc2]I2 and [ZrPc2]I2
    Janczak, J
    Idemori, YM
    INORGANICA CHIMICA ACTA, 2001, 325 (1-2) : 85 - 93
  • [38] Revolution of iodine electrochemistry: From I-/I2 to I- /I5+
    Zhu, Yunhai
    Cui, Yangfeng
    Yang, Hui Ying
    MATTER, 2024, 7 (08) : 2769 - 2770
  • [39] Synthesis and Characterization of Semiconductor Polymer Doped with FeCl3 and I2
    Daho, Bouabdallah
    Fontanesi, Claudio
    Messori, Massimo
    Dehbi, Abdelkader
    Abdelkader, Belfedal
    SEMICONDUCTORS, 2019, 53 (12) : 1656 - 1664
  • [40] SYNTHESIS OF ISATIN 3-OXIMES FROM 2-NITROACETANILIDES
    KEARNEY, T
    HARRIS, PA
    JACKSON, A
    JOULE, JA
    SYNTHESIS-STUTTGART, 1992, (08): : 769 - 772