Azatripyrrolic and Azatetrapyrrolic Macrocycles from the Mannich Reaction of Pyrrole: Receptors for Anions

被引:27
|
作者
Mani, Ganesan [1 ]
Jana, Debasish [1 ]
Kumar, Rajnish [1 ]
Ghorai, Debasish [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
X-RAY-STRUCTURE; CONVENIENT SYNTHESIS; BINDING PROPERTIES; HOST; RECOGNITION; CALIXPYRROLES; COMPLEXES;
D O I
10.1021/ol101159q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Azatripyrrolic 1 and azatetrapyrrolic 2 macrocycles were synthesized in a single step by the Mannich reaction of pyrrole in the presence of primary amine hydrochloride and were structurally characterized among several other higher analogue azapyrrolic macrocycles. Binding constants for the halide anion complexes are determined by H-1 NMR titrations and they show different binding stoichiometries
引用
收藏
页码:3212 / 3215
页数:4
相关论文
共 50 条
  • [1] Oligopyrrole macrocycles as receptors for cations and anions
    Sessler, Jonathan L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [2] Mannich reaction of pyrrole and dimethylpyrrole with monoamines and diamines
    Jana, Debasish
    Guchhait, Tapas
    Subramaniyan, Vasudevan
    Kumar, Ashok
    Mani, Ganesan
    TETRAHEDRON LETTERS, 2019, 60 (46)
  • [3] POLYAMINE POLYMERS FROM PYRROLE, FORMALIN, AND AMINES BY USE OF MANNICH REACTION
    TSUCHIDA, E
    TOMONO, T
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1973, 11 (04) : 723 - 735
  • [4] Indole-based macrocycles as a class of receptors for anions
    Chang, KJ
    Moon, D
    Lah, MS
    Jeong, KS
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) : 7926 - 7929
  • [5] THE PREPARATION OF SOME MONOSUBSTITUTED DERIVATIVES OF PYRROLE BY THE MANNICH REACTION
    HERZ, W
    DITTMER, K
    CRISTOL, SJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (07) : 1698 - 1700
  • [6] Mannich Reaction: An Alternative Synthetic Approach for Various Pyrrole-Based Anion Receptors and Chelating Ligands
    Guchhait, Tapas
    Roy, Satabdi
    Jena, Priyadarshini
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (34)
  • [7] Reaction of pyrrole anions with carbon disulfide. Synthesis of pyrrole-3-carbodithioates
    Trofimov, BA
    Sobenina, LN
    Mikhaleva, AI
    Demenev, AP
    Tarasova, OA
    Ushakov, IA
    Zinchenko, SV
    TETRAHEDRON, 2000, 56 (37) : 7325 - 7329
  • [8] Ab initio Study of the Reaction of Pyrrole Anions with Carbon Disulfide
    V. B. Kobychev
    N. M. Vitkovskaya
    I. L. Zaitseva
    E. Yu. Larionova
    B. A. Trofimov
    Journal of Structural Chemistry, 2001, 42 : 536 - 543
  • [9] Ab initio study of the reaction of pyrrole anions with carbon disulfide
    Kobychev, VB
    Vitkovskaya, NM
    Zaitseva, IL
    Larionova, EY
    Trofimov, BA
    JOURNAL OF STRUCTURAL CHEMISTRY, 2001, 42 (04) : 536 - 543
  • [10] Ferrocene-amino acid macrocycles as hydrazone-based receptors for anions
    Beeren, Sophie R.
    Sanders, Jeremy K. M.
    CHEMICAL SCIENCE, 2011, 2 (08) : 1560 - 1567