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
来源：
DYES AND PIGMENTS | 2020年 / 173卷
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
  • [21] Pd(II)-Catalyzed C-H Iodination Using Molecular I2 as the Sole Oxidant
    Wang, Xiao-Chen
    Hu, Yi
    Bonacorsi, Samuel
    Hong, Yang
    Burrell, Richard
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (28) : 10326 - 10329
  • [22] Synthesis of Amides from Aliphatic Acids and Amines by using of I2/TBHP at Room Temperature
    Sirgamalla, Rambabu
    Kommakula, Ashok
    Banoth, Sonyanaik
    Dharavath, Ravi
    Adem, Kurumanna
    Madhu, P.
    Boda, Sakram
    CHEMISTRYSELECT, 2018, 3 (04): : 1062 - 1065
  • [23] Regioselective synthesis of α-iodoacetates from alkenes/ammonium acetate/I2 by Woodward's reaction
    Myint, YY
    Pasha, MA
    SYNTHETIC COMMUNICATIONS, 2004, 34 (24) : 4477 - 4482
  • [24] Synthesis of Tricyclic Spiranoid Lactones via I2/Sm(II)- and I2/Pd(0)-Mediated Cyclizations of a Common Cycloalkylmethylene Precursor
    Mostinski, Yelena
    Valerio, Viviana
    Lankri, David
    Tsvelikhovsky, Dmitry
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21): : 10464 - 10473
  • [25] Synthesis of vinyl sulfones from terminal olefins and sulfonyl chloride derivatives catalyzed by copper(I) chloride/I2
    Sun, W. (wsun@licp.cas.cn), 1600, Science Press, 16 Donghuangchenggen North Street, Beijing, 100717, China (27):
  • [26] An I2/amine synergistic catalysis enables 2,2′-bipyridine synthesis from oxime esters and enals
    Jin, Xiao-Kun
    Zhou, Jia-Hao
    Zeng, Han-Ying
    Zheng, Mei-Jun
    Li, Zi-Hao
    Wei, Ye
    Jiang, Kun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (13) : 3081 - 3092
  • [27] The convenient synthesis of benzimidazole derivatives catalyzed by I2 in aqueous media
    Sun, Peipei
    Hu, Zhixin
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (03) : 773 - 775
  • [28] Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions
    Zhang, Zhenlei
    Yang, Jiusi
    Yu, Renjie
    Wu, Kairui
    Bu, Jiping
    Li, Shaoke
    Qian, Peng
    Sheng, Liangquan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (37) : 5209 - 5212
  • [29] Synthesis and characterization of complex containing ferroceneyl Cd(dppf)I2
    Huang, ZX
    Wang, XL
    Liu, SX
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2002, 18 (11) : 1119 - 1122
  • [30] PROSTAGLANDIN-I2 (PG I2 - PROSTACYCLIN) SYNTHESIS BY HUMAN GASTRIC-MUCOSA
    SINZINGER, H
    SILBERBAUER, K
    SEYFRIED, H
    WINTER, M
    WIENER KLINISCHE WOCHENSCHRIFT, 1979, 91 (22) : 768 - 771
12345