Synthesis of trimethylammoniumphenylthio-substituted phthalocyanines with different pattern of substitution

被引：29
|
作者：
Giuntini, F
Nistri, D
Chiti, G
Fantetti, L
Jori, G
Roncucci, G
机构：
[1] Molteni Farmaceut, I-50018 Scandicci, FI, Italy
[2] Univ Padua, Dipartimento Fotobiol, I-35121 Padua, Italy
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 03期
关键词：
zinc(II)phthalocyanines; phthalonitriles; cationic photosensitizers; PDT;
D O I：
10.1016/S0040-4039(02)02597-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The base-catalyzed cyclotetramerization of 3-, 4- and 4,5-dimethylaminophenylthio phthalonitriles with zinc(II)acetate afforded 1(4),8(11),15(18),22(25)- and 2(3),9(10),16(17),23(24)-tetrasubstituted and 2,3,9,10,16,17,23,24-octasubstituted Zn(II)phthalocyanines, respectively. The statistical mixed condensation of the same phthalonitriles with 1,2-dicyanobenzene gave the corresponding mono- and disubstituted derivatives. Methylation of such products afforded a series of cationic Zn(II)phthalocyanines with different pattern of substitution, with potential use as photodynamic agents in microbial infections. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：515 / 517
页数：3
相关论文
共 20 条
  • [1] Synthesis of substituted phthalocyanines
    Nemykin, Victor N.
    Lukyanets, Evgeny A.
    ARKIVOC, 2010, : 136 - 208
  • [2] Synthesis of sulfonamide-substituted phthalocyanines
    Carvalho, Eliana F. A.
    Calvete, Mario J. F.
    Tome, Augusto C.
    Cavaleiro, Jose A. S.
    TETRAHEDRON LETTERS, 2009, 50 (49) : 6882 - 6885
  • [3] Aromatic Nucleophilic Substitution as a Side Process in the Synthesis of Alkoxy- and Crown-Substituted (Na)phthalocyanines
    Martynov, Alexander G.
    Berezhnoy, Georgy S.
    Safonova, Evgeniya A.
    Polovkova, Marina A.
    Gorbunova, Yulia G.
    Tsivadze, Aslan Yu
    MACROHETEROCYCLES, 2019, 12 (01): : 75 - 81
  • [4] Synthesis and antimycotic activity of new unsymmetrical substituted zinc phthalocyanines
    Cosimelli, B
    Roncucci, G
    Dei, D
    Fantetti, L
    Ferroni, F
    Ricci, M
    Spinelli, D
    TETRAHEDRON, 2003, 59 (50) : 10025 - 10030
  • [5] Phthalocyanine synthesis in ionic liquids: Preparation of differently substituted phthalocyanines in tetrabutylammonium bromide
    Lo, PC
    Cheng, DYY
    Ng, DKP
    SYNTHESIS-STUTTGART, 2005, (07): : 1141 - 1147
  • [6] Synthesis of non-peripherally substituted tetra(dihexylmalonate) alcohol soluble phthalocyanines
    Korkut, Sibel Eken
    Avciata, Ulvi
    Sener, M. Kasim
    JOURNAL OF COORDINATION CHEMISTRY, 2011, 64 (16) : 2936 - 2944
  • [7] Phthalocyanines and related compounds: XLIII. Synthesis of poly[phenyl(alkyl)sulfanyl]-substituted phthalonitriles and some phthalocyanines based thereon
    K. A. Volkov
    G. V. Avramenko
    V. M. Negrimovskii
    E. A. Luk’yanets
    Russian Journal of General Chemistry, 2007, 77 : 1108 - 1116
  • [8] Phthalocyanines and related compounds: XLVIII. Stepwise nucleophilic substitution in tetrachlorophthalonitrile: Synthesis of polysubstituted phthalonitriles
    K. A. Volkov
    V. M. Negrimovskii
    G. V. Avramenko
    E. A. Luk’yanets
    Russian Journal of General Chemistry, 2008, 78 : 1794 - 1801
  • [9] Phthalocyanines and Related Compounds: XLVIII. Stepwise Nucleophilic Substitution in Tetrachlorophthalonitrile: Synthesis of Polysubstituted Phthalonitriles
    Volkov, K. A.
    Negrimovskii, V. M.
    Avramenko, G. V.
    Luk'yanets, E. A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (09) : 1794 - 1801
  • [10] Synthesis and Spectral Properties of Low-Symmetry Phenoxy(chloro) and Phenylsulfanyl(chloro) Substituted Phthalocyanines
    Koptyaev, Andrey I.
    Galanin, Nikolay E.
    Shaposhnikov, Gennady P.
    MACROHETEROCYCLES, 2015, 8 (02): : 156 - 161
12