Disazo dyes containing pyrazole and benzothiazole moieties: synthesis, characterization, absorption characteristics and tautomeric structures

被引:4
作者
Cicen, Gulsah [1 ]
Atay, Cigdem Karabacak [2 ]
Tilki, Tahir [1 ]
机构
[1] Suleyman Demirel Univ, Fac Sci & Arts, Chem Dept, TR-32260 Isparta, Turkey
[2] Mehmet Akif Ersoy Univ, Educ Fac, Basic Educ Dept, TR-15030 Burdur, Turkey
关键词
Disazo dye; Benzothiazole; Pyrazole; Absorption property; Tautomerization; AZO DYES; DERIVATIVES; DESIGN; AGENTS;
D O I
10.1007/s11164-017-3021-5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Eight newly synthesized disazo disperse dyes containing benzothiazole and pyrazole moieties were prepared by diazotization of 2-aminobenzothiazole, coupling with 3-aminocrotononitrile as active methylene, cyclization reactions with hydrazine hydrate and phenyl hydrazine, diazotization again and finally coupling with dimedone, dioxane, 1-methyl imidazole and 2-methyl imidazole, respectively. Their structures were characterized with spectroscopic methods (FT-IR, H-1-NMR, C-13-NMR) and solvatochromic properties were studied with UV-Vis spectroscopy in different solvents. Tautomeric structures of synthesized dyes were also examined in detail.
引用
收藏
页码:6803 / 6816
页数:14
相关论文
共 17 条
[1]   Antimicrobial activities and absorption properties of disazo dyes containing imidazole and pyrazole moieties [J].
Atay, Cigdem Karabacak ;
Gokalp, Merve ;
Tuncer, Banu Ozden ;
Tilki, Tahir .
JOURNAL OF MACROMOLECULAR SCIENCE PART A-PURE AND APPLIED CHEMISTRY, 2017, 54 (04) :236-242
[2]   Synthesis and spectroscopic characterization of an alkoxysilane dye containing azo-benzothiazole chromophore for nonlinear optical applications [J].
Chen, Lujian ;
Cui, Yuanjing ;
Qian, Guodong ;
Wang, Minquan .
DYES AND PIGMENTS, 2007, 73 (03) :338-343
[3]   Design and synthesis of new potent anticancer benzothiazole amides and ureas featuring pyridylamide moiety and possessing dual B-RafV600E and C-Raf kinase inhibitory activities [J].
El-Damasy, Ashraf Kareem ;
Lee, Ju-Hyeon ;
Seo, Seon Hee ;
Cho, Nam-Chul ;
Pae, Ae Nim ;
Keum, Gyochang .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 115 :201-216
[4]   Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of benzothiazole derivatives [J].
Gabr, Moustafa T. ;
El-Gohary, Nadia S. ;
El-Bendary, Eman R. ;
El-Kerdawy, Mohamed M. ;
Ni, Nanting ;
Shaaban, Mona I. .
CHINESE CHEMICAL LETTERS, 2015, 26 (12) :1522-1528
[5]   Synthesis, characterization and electrochemical studies of azo dyes derived from barbituric acid [J].
Harisha, S. ;
Keshavayya, Jathi ;
Swamy, B. E. Kumara ;
Viswanath, C. C. .
DYES AND PIGMENTS, 2017, 136 :742-753
[6]   Antimicrobial pyrazole dyes: synthesis, characterization, and absorption characteristics [J].
Karabacak, Cigdem ;
Tilki, Tahir ;
Tuncer, Banu Ozden ;
Cengiz, Mustafa .
RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (04) :1985-1999
[7]   Synthesis of some novel pyrazolo[5,1-c][l,2,4]triazine derivatives and investigation of their absorption spectra [J].
Karci, Fati ;
Karci, Fikret .
DYES AND PIGMENTS, 2008, 76 (01) :97-103
[8]   Novel cycloalkylthiophene-imine derivatives bearing benzothiazole scaffold: Synthesis, characterization and antiviral activity evaluation [J].
Ke, Shaoyong ;
Wei, Yanhong ;
Yang, Ziwen ;
Wang, Kaimei ;
Liang, Ying ;
Shi, Liqiao .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (18) :5131-5134
[9]   The immunomodulation potential of the synthetic derivatives of benzothiazoles: Implications in immune system disorders through in vitro and in silico studies [J].
Khan, Khalid Mohammed ;
Mesaik, Mohammad A. ;
Abdalla, Omer M. ;
Rahim, Fazal ;
Soomro, Samreen ;
Halim, Sobia A. ;
Mustafa, Ghulam ;
Ambreen, Nida ;
Khalid, Ahmad Shukralla ;
Taha, Muhammad ;
Perveen, Shahnaz ;
Alam, Muhammad Tanveer ;
Hameed, Abdul ;
Ul-Haq, Zaheer ;
Ullah, Hayat ;
Rehman, Zia Ur ;
Siddiqui, Rafat Ali ;
Voelter, Wolfgang .
BIOORGANIC CHEMISTRY, 2016, 64 :21-28
[10]   Design, synthesis, biological evaluation and preliminary mechanism study of novel benzothiazole derivatives bearing indole-based moiety as potent antitumor agents [J].
Ma, Junjie ;
Bao, Guanglong ;
Wang, Limei ;
Li, Wanting ;
Xu, Boxuan ;
Du, Baoquan ;
Lv, Jie ;
Zhai, Xin ;
Gong, Ping .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 96 :173-186