Singlet oxygen-mediated transformation of furans into aromatic nitrogen-containing polycycles in water

被引:7
|
作者
Kalaitzakis, Dimitris [1 ]
Montagnon, Tamsyn [1 ]
Ioannou, Georgios I. [1 ]
Antonatou, Eirini [1 ]
Vassilikogiannakis, Georgios [1 ]
机构
[1] Univ Crete, Dept Chem, Iraklion 71003, Crete, Greece
基金
欧洲研究理事会;
关键词
Singlet oxygen; furans; water; sustainable chemistry; green chemistry; indole; tryptamine; Pictet-Spengler; ONE-POT SYNTHESIS; ECONOMY; PHOTOOXIDATION; SYNTHESIZE; PRODUCTS;
D O I
10.3998/ark.5550190.p008.973
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using a sustainable, green and one-pot protocol, simple furans are transformed into complex aromatic nitrogen-bearing polycycles that are synthetically important. The reaction, which is performed in water, begins with the highly selective and mild photooxidation of the furan substrate with singlet oxygen.
引用
收藏
页码:154 / 166
页数:13
相关论文
共 50 条
  • [1] From Simple Furans to Complex Nitrogen-Bearing Aromatic Polycycles by Means of a Flexible and General Reaction Sequence Initiated by Singlet Oxygen
    Kalaitzakis, Dimitris
    Montagnon, Tamsyn
    Antonatou, Eirini
    Bardaji, Nuria
    Vassilikogiannakis, Georgios
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (31) : 10119 - 10123
  • [2] Regiocontrolled Synthesis of γ-Hydroxybutenolides via Singlet Oxygen-Mediated Oxidation of 2-Thiophenyl Furans
    Kotzabasaki, Vasilild
    Vassilikogiannakis, Georgios
    Stratakis, Manolis
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10): : 4406 - 4411
  • [3] Polyhedral phenylnickelsodiumsiloxanolate transformation in the presence of aromatic nitrogen-containing ligands
    Anisimov, Anton A.
    Vysochinskaya, Yulia S.
    Kononevich, Yuriy N.
    Dolgushin, Fedor M.
    Muzafarov, Aziz M.
    Shchegolikhina, Olga, I
    INORGANICA CHIMICA ACTA, 2021, 517
  • [4] TRANSFORMATION OF NITROGEN-CONTAINING AROMATIC RADICAL CATIONS INTO PROTONATED SUBSTRATES
    HANDOO, KL
    CHENG, JP
    PARKER, VD
    ACTA CHEMICA SCANDINAVICA, 1993, 47 (06): : 626 - 628
  • [5] Singlet oxygen-mediated damage to proteins and its consequences
    Davies, MJ
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2003, 305 (03) : 761 - 770
  • [6] Singlet oxygen-mediated synthesis of malarial chemotherapeutic agents
    Malik, Sachin
    Khan, Suroor A.
    Ahuja, Priya
    Arya, Satish K.
    Sahu, Shikha
    Sahu, Kapendra
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (12) : 5633 - 5653
  • [7] Singlet oxygen-mediated synthesis of malarial chemotherapeutic agents
    Sachin Malik
    Suroor A. Khan
    Priya Ahuja
    Satish K. Arya
    Shikha Sahu
    Kapendra Sahu
    Medicinal Chemistry Research, 2013, 22 : 5633 - 5653
  • [8] Singlet oxygen-mediated formation of protein peroxides within cells
    Davies, MJ
    Hawkins, C
    Wright, A
    FREE RADICAL BIOLOGY AND MEDICINE, 2002, 33 : S420 - S420
  • [9] Kinetic parameters of the transformation of nitrogen-containing compounds in natural water
    Ryzhakov, A. V.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2013, 83 (13) : 2618 - 2623
  • [10] Kinetic parameters of the transformation of nitrogen-containing compounds in natural water
    A. V. Ryzhakov
    Russian Journal of General Chemistry, 2013, 83 : 2618 - 2623