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5-(3'-Amino-4'-arilazo-1H-pirazol-5'-il azo) barbitürik asit boyarmaddelerin sentezi ve spektroskopik özelliklerinin incelenmesi

Yıl 2018, Cilt: 24 Sayı: 7, 1293 - 1297, 28.12.2018

Öz

Bu
çalışmada öncelikle anilin türevleri diazolanmış ve daha sonra diazolanan bu
bileşikler, aril-azo-malononitril (1a-1m) bileşiklerini sentezlemek için
malononitril ile reaksiyona sokulmuştur. İkinci olarak
4-arilazo-3,5-diamino-1H-pirazol (2a-2m) türevleri, aril-azo-malononitril
(1a-1m) bileşikleri ile hidrazin monohidrat etkileştirilerek sentezlenmiştir.
Son olarak bu bileşiklerin diazonyum tuzları barbitürik asit ile reaksiyona
sokulmuş ve hedef bileşikler olan 5-(3'-amino-4'-arilazo-1H-pirazol-5'-il-azo)
barbitürik asit (3a-3m) bileşikleri elde edilmiştir. 3a-3m bileşiklerinin
yapıları AT-IR, 1H-NMR ve Ultraviyole–görünür bölge spektroskopisi gibi
spektral yöntemlerle karakterize edilmiştir. Sonuç olarak azo boyarmadde ve
tekstil literatürüne 13 adet yeni pirazol türevi dispers disazo boyarmaddeleri
kazandırılmıştır.

Kaynakça

  • Dawson JF. “The Structure and properties of disperse dyes ın polyester coloration”. Journal of The Society of Dyers and Colourists, 99, 183, 1983.
  • Dawson JF. “Developments in disperse dyes”. Review of Progress in Coloration and Related Topics, 9, 25-35, 1978.
  • Dawson JF. “Fifty years of disperse dyes (1934-1984)”. Review of Progress in Coloration and Related Topics, 14, 90-97, 1984.
  • Schwander HR. “Heterocyclic azo coupling components”. Dyes and Pigments, 3, 133-160, 1982.
  • Sabnis RW, Rangnekar DW. “Synthesis of 2-Azo-3-cyano-5-carbethoxy thiophene derivatives and their application on polyester fibers”. Journal Chem. Tech. Biotechnol, 47, 39-46, 1990.
  • Sabnis RW, Kazem G, Rangnekar DW. “Synthesis and application of 5-arylazothiophene derivatives”. Bulletin of the Chemical Society of Japan, 64, 3768-3770, 1991.
  • Hanna MA, Girges MM, Fadda AA. “New Dyestuffs for polyester fibers-synthesis and comparative tinctorial behavior of 3-alkyl-4-arylhydrazono-n-1-picolinoyl-2-pyrazolin-5-ones and their ısomeric pyrid-3-yl analogs and pyrid-4-yl analogs”. Journal of Chemical Technology and Biotechnogy, 55, 9-16, 1992.
  • Ayyangar NR, Lahoti RJ, Lugagade, AG. “Synthesis of monoazo disperse dyes from 5-amino-3-Methyl-1-(3',5'-disubstituted) S-triazinylpyrazoles and a study of their visible absorption and dyeing properties”. Journal of the Society Dyers andColourists, 102, 176-181, 1986.
  • Mikroyannidis JA, Tsagkournos DV, Balraju P, Sharma GD. “Low band gap dyes based on 2-styryl-5-phenylazo-pyrrole: Synthesis and application for efficient dye-sensitized solar cells”. Journal of Power Sources, 196, 4152-4161, 2011.
  • Adegoke OA, Adesuji TE, Thomas OE. “Novel colorimetric sensors for cyanide based on azo-hydrazone tautomeric skeletons”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 128, 147-152, 2014.
  • Yousefi H, Yahyazadeh A, Moradi Rufchahi EO, Rassa M. “Synthesis, spectral properties, biological activity and application of new 4-(benzyloxy)phenol derived azo dyes for polyester fiber dyeing”. Journal of Molecular Liquids, 180, 51-58, 2013.
  • Karcı F, Karcı F, Demirçalı A, Yamaç M. “Synthesis, solvatochromic properties and antimicrobial activities of some novel pyridone-based disperse disazo dyes”. Journal of Molecular Liquids, 187, 302-1308, 2013.
  • Karcı F, Demircalı A, Karcı F, Kara I, Ucun F. “The synthesis, spectroscopic properties and theoretical calculation of some novel disperse disazo dyes derived from 3-amino-5-hydroxy-1-phenylpyrazole”. Journal of Molecular Structure, 935, 19–26, 2009.
  • Karci F, Demircali A. “Synthesis of disazo pyrazolo [1,5-a] pyrimidines”. Dyes Pigments 74, 288-297, 2007.
  • Karci F, Karci F. “Synthesis and absorption spectra of some novel heterocyclic disazo dyes derived from pyridone and pyrazolone derivatives”. Dyes Pigments, 76, 147-157, 2008.
  • Zayed MA, Mohamed GG, Abdullah SAM. “Synthesis, structure investigation, spectral characteristics and biological activities of some novel azodyes”. Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 78, 1027-1036, 2011.
  • Yazdanbakhsh MR, Yousefi H, Mamaghani M, Moradi EO, Rassa M. Pouramir H., Bagheri M., “Synthesis, spectral characterization and antimicrobial activity of some new azo dyes derived from 4,6-dihydroxypyrimidine”. Journal of Molecular Liquids, 169, 21-26, 2012.
  • Yousefi H, Yahyazadeh A, Moradi Rufchahi EO, Rassa M. “Synthesis, spectral properties, biological activity and application of new 4-(benzyloxy)phenol derived azo dyes for polyester fiber dyeing”. Journal of Molecular Liquids, 180, 51–58, 2013.

Synthesis of 5-(3'-amino-4'-arylazo-1H-pyrazol-5'-yl azo) barbituric acid dyes and investigation of spectroscopic properties

Yıl 2018, Cilt: 24 Sayı: 7, 1293 - 1297, 28.12.2018

Öz

In
this study, firstly aniline derivatives were diazotized and then these
diazotized compounds were reacted with malononitrile for synthesizing the
aril-azo malononitrile compounds (1a-1m). Secondly,
4-arylazo-3,5-diamino-1H-pyrazole (2a-2m) derivatives were synthesized by
effecting hydrazine monohydrate with aril-azo malononitrile compounds (1a-1m). Finally, the diazonium salts of these compounds were reacted with
barbituric acid and 5-(3'-amino-4'-arylazo-1H-pyrazole-5'-yl-azo) barbituric
acid compounds (3a-3m) which target compounds were obtained. The structures of
(3a-3m) compounds were characterized with AT-IR, 1H-NMR and UV–visible
spectroscopy. As a result, it was gained 13 novel disperse disazo dyes to azo
dye and textile literature.

Kaynakça

  • Dawson JF. “The Structure and properties of disperse dyes ın polyester coloration”. Journal of The Society of Dyers and Colourists, 99, 183, 1983.
  • Dawson JF. “Developments in disperse dyes”. Review of Progress in Coloration and Related Topics, 9, 25-35, 1978.
  • Dawson JF. “Fifty years of disperse dyes (1934-1984)”. Review of Progress in Coloration and Related Topics, 14, 90-97, 1984.
  • Schwander HR. “Heterocyclic azo coupling components”. Dyes and Pigments, 3, 133-160, 1982.
  • Sabnis RW, Rangnekar DW. “Synthesis of 2-Azo-3-cyano-5-carbethoxy thiophene derivatives and their application on polyester fibers”. Journal Chem. Tech. Biotechnol, 47, 39-46, 1990.
  • Sabnis RW, Kazem G, Rangnekar DW. “Synthesis and application of 5-arylazothiophene derivatives”. Bulletin of the Chemical Society of Japan, 64, 3768-3770, 1991.
  • Hanna MA, Girges MM, Fadda AA. “New Dyestuffs for polyester fibers-synthesis and comparative tinctorial behavior of 3-alkyl-4-arylhydrazono-n-1-picolinoyl-2-pyrazolin-5-ones and their ısomeric pyrid-3-yl analogs and pyrid-4-yl analogs”. Journal of Chemical Technology and Biotechnogy, 55, 9-16, 1992.
  • Ayyangar NR, Lahoti RJ, Lugagade, AG. “Synthesis of monoazo disperse dyes from 5-amino-3-Methyl-1-(3',5'-disubstituted) S-triazinylpyrazoles and a study of their visible absorption and dyeing properties”. Journal of the Society Dyers andColourists, 102, 176-181, 1986.
  • Mikroyannidis JA, Tsagkournos DV, Balraju P, Sharma GD. “Low band gap dyes based on 2-styryl-5-phenylazo-pyrrole: Synthesis and application for efficient dye-sensitized solar cells”. Journal of Power Sources, 196, 4152-4161, 2011.
  • Adegoke OA, Adesuji TE, Thomas OE. “Novel colorimetric sensors for cyanide based on azo-hydrazone tautomeric skeletons”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 128, 147-152, 2014.
  • Yousefi H, Yahyazadeh A, Moradi Rufchahi EO, Rassa M. “Synthesis, spectral properties, biological activity and application of new 4-(benzyloxy)phenol derived azo dyes for polyester fiber dyeing”. Journal of Molecular Liquids, 180, 51-58, 2013.
  • Karcı F, Karcı F, Demirçalı A, Yamaç M. “Synthesis, solvatochromic properties and antimicrobial activities of some novel pyridone-based disperse disazo dyes”. Journal of Molecular Liquids, 187, 302-1308, 2013.
  • Karcı F, Demircalı A, Karcı F, Kara I, Ucun F. “The synthesis, spectroscopic properties and theoretical calculation of some novel disperse disazo dyes derived from 3-amino-5-hydroxy-1-phenylpyrazole”. Journal of Molecular Structure, 935, 19–26, 2009.
  • Karci F, Demircali A. “Synthesis of disazo pyrazolo [1,5-a] pyrimidines”. Dyes Pigments 74, 288-297, 2007.
  • Karci F, Karci F. “Synthesis and absorption spectra of some novel heterocyclic disazo dyes derived from pyridone and pyrazolone derivatives”. Dyes Pigments, 76, 147-157, 2008.
  • Zayed MA, Mohamed GG, Abdullah SAM. “Synthesis, structure investigation, spectral characteristics and biological activities of some novel azodyes”. Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 78, 1027-1036, 2011.
  • Yazdanbakhsh MR, Yousefi H, Mamaghani M, Moradi EO, Rassa M. Pouramir H., Bagheri M., “Synthesis, spectral characterization and antimicrobial activity of some new azo dyes derived from 4,6-dihydroxypyrimidine”. Journal of Molecular Liquids, 169, 21-26, 2012.
  • Yousefi H, Yahyazadeh A, Moradi Rufchahi EO, Rassa M. “Synthesis, spectral properties, biological activity and application of new 4-(benzyloxy)phenol derived azo dyes for polyester fiber dyeing”. Journal of Molecular Liquids, 180, 51–58, 2013.
Toplam 18 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Makale
Yazarlar

Aykut Demirçalı Bu kişi benim 0000-0002-6879-9993

Yayımlanma Tarihi 28 Aralık 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 24 Sayı: 7

Kaynak Göster

APA Demirçalı, A. (2018). 5-(3’-Amino-4’-arilazo-1H-pirazol-5’-il azo) barbitürik asit boyarmaddelerin sentezi ve spektroskopik özelliklerinin incelenmesi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, 24(7), 1293-1297.
AMA Demirçalı A. 5-(3’-Amino-4’-arilazo-1H-pirazol-5’-il azo) barbitürik asit boyarmaddelerin sentezi ve spektroskopik özelliklerinin incelenmesi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. Aralık 2018;24(7):1293-1297.
Chicago Demirçalı, Aykut. “5-(3’-Amino-4’-Arilazo-1H-Pirazol-5’-Il Azo) barbitürik Asit Boyarmaddelerin Sentezi Ve Spektroskopik özelliklerinin Incelenmesi”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 24, sy. 7 (Aralık 2018): 1293-97.
EndNote Demirçalı A (01 Aralık 2018) 5-(3’-Amino-4’-arilazo-1H-pirazol-5’-il azo) barbitürik asit boyarmaddelerin sentezi ve spektroskopik özelliklerinin incelenmesi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 24 7 1293–1297.
IEEE A. Demirçalı, “5-(3’-Amino-4’-arilazo-1H-pirazol-5’-il azo) barbitürik asit boyarmaddelerin sentezi ve spektroskopik özelliklerinin incelenmesi”, Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, c. 24, sy. 7, ss. 1293–1297, 2018.
ISNAD Demirçalı, Aykut. “5-(3’-Amino-4’-Arilazo-1H-Pirazol-5’-Il Azo) barbitürik Asit Boyarmaddelerin Sentezi Ve Spektroskopik özelliklerinin Incelenmesi”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 24/7 (Aralık 2018), 1293-1297.
JAMA Demirçalı A. 5-(3’-Amino-4’-arilazo-1H-pirazol-5’-il azo) barbitürik asit boyarmaddelerin sentezi ve spektroskopik özelliklerinin incelenmesi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. 2018;24:1293–1297.
MLA Demirçalı, Aykut. “5-(3’-Amino-4’-Arilazo-1H-Pirazol-5’-Il Azo) barbitürik Asit Boyarmaddelerin Sentezi Ve Spektroskopik özelliklerinin Incelenmesi”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, c. 24, sy. 7, 2018, ss. 1293-7.
Vancouver Demirçalı A. 5-(3’-Amino-4’-arilazo-1H-pirazol-5’-il azo) barbitürik asit boyarmaddelerin sentezi ve spektroskopik özelliklerinin incelenmesi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. 2018;24(7):1293-7.





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