A facile synthesis of some new pyrazolo[1,5-a]pyrimidine heterocyclic disazo dyes and an evaluation of their solvatochromic behaviour

被引:46
|
作者
Tsai, Pi Chen [1 ]
Wang, Ing Jing [1 ]
机构
[1] Natl Taiwan Univ Sci & Technol, Dept Polymer Engn, Taipei 10772, Taiwan
关键词
hetarylazopyrazole; dihetarylazo-pyrazolo[1,5-a]pyrimidine; disazo dyes; solvents' effect;
D O I
10.1016/j.dyepig.2006.03.022
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Hetarylmalononitriles (thiazolylmalononitrile and benzothiazolylmalononitrile) were prepared by the coupling reaction of malononitrile with heterocyclic amines in nitrosyl sulfuric acid. 4-Hetarylazo-3,5-diaminopyrazole compounds were obtained by the reaction of hetarylmalononitriles with hydrazine hydrate (64%). Both compounds can react with arylazo- and hetarylazornalononitriles to give 3,6-di-(aryl or hetaryl)azo-2,5,7-triaminopyrazolo[1,5-a]pyrimidine heterocyclic disazo dyes. These dyes were characterized by elemental and spectral analyses (IR, H-1 NMR and mass). The solvatochromic behaviour in various solvents was evaluated. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:578 / 584
页数:7
相关论文
共 50 条
  • [1] Synthesis and solvatochromic properties of some disazo dyes derived from pyrazolo[1,5-a]pyrimidine derivatives
    Tsai, PC
    Wang, IJ
    DYES AND PIGMENTS, 2005, 64 (03) : 259 - 264
  • [2] Synthesis and application of disazo reactive dyes derived from sulfatoethylsulfone pyrazolo[1,5-a]pyrimidine derivatives
    Youssef, Y. A.
    Kamel, Magda M.
    Taher, M. S.
    Ali, N. F.
    Abd El Megiede, Saadia A.
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2014, 18 (03) : 220 - 226
  • [3] Synthesis of disazo pyrazolo[1,5-a]pyrimidines
    Karci, Fikret
    Demirçali, Aykut
    DYES AND PIGMENTS, 2007, 74 (02) : 288 - 297
  • [4] Synthesis of Some Novel Pyrazolo[1,5-a]pyrimidine Derivatives and Their Application as Disperse Dyes
    Al-Etaibi, Alya M.
    Al-Awadi, Nouria A.
    El-Apasery, Morsy A.
    Ibrahim, Maher R.
    MOLECULES, 2011, 16 (06) : 5182 - 5193
  • [5] The synthesis of new pyrazolo[1,5-a]pyrimidine derivatives
    Marjani, Ahmad Poursattar
    Khalafy, Jabbar
    Salami, Fatemeh
    Ezzati, Mahnaz
    ARKIVOC, 2015, : 277 - 286
  • [6] HETEROCYCLIC SYNTHESIS WITH NITRILES - SYNTHESES OF SOME NOVEL PYRAZOLO[1,5-A]PYRIMIDINE AND PYRROLO[2',3'-3,4]PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES
    ABDELRAZEK, FM
    JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (03): : 475 - 478
  • [7] Synthesis and Cytotoxic Activity of Some New Pyrazolo[1,5-a]pyrimidine Derivatives
    Gouda, Moustafa A.
    Barnawi, Ibrahim O.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 31 (01) : 119 - 123
  • [8] ALPHA,BETA-UNSATURATED NITRILES IN HETEROCYCLIC SYNTHESIS - SYNTHESIS OF SOME NEW PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES
    ELAGAMEY, AGA
    ABDALLA, SO
    ELMOGHAYAR, MRH
    MONATSHEFTE FUR CHEMIE, 1984, 115 (12): : 1413 - 1419
  • [9] Synthesis and solvatochromic properties of 3,6-bis-hetarylazo dyes derived from pyrazolo[1,5-a]pyrimidine
    Tsai, Pi Chen
    Wang, Ing Jing
    DYES AND PIGMENTS, 2008, 76 (03) : 575 - 581
  • [10] REACTIONS WITH HETEROCYCLIC AMIDINES .3. SYNTHESIS OF SOME NEW PYRAZOLO[1,5-A]PYRIMIDINE AND PYRAZOLO[1,5-C]-AS-TRIAZINE DERIVATIVES
    ELAGAMEY, AGA
    ELTAWEEL, FMA
    AMER, FA
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1986, 51 (10) : 2193 - 2198