European Journal of Chemistry 2012, 3(1), 44-50. doi:10.5155/eurjchem.3.1.44-50.517

Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol


Hitendra Mangubhai Patel (1,*)

(1) Department of Chemistry, Vithalbhai Patel and Rajratna Purushotamdas Tulsibhai Patel Science College, Sardar Patel University, Vallabh Vidyanagar, Gujarat, 388120, India
(*) Corresponding Author

Received: 31 Aug 2011, Accepted: 15 Nov 2011, Published: 31 Mar 2012

Abstract


Aniline derivatives were diazotized and coupled with 3-aminocrotononitrile to give the corresponding 2-arylhydrazono-3-ketiminobutyronitriles. Cyclization of these arylhydrazono derivatives with hydrazine monohydrate afforded 5-amino-4-arylazo-3-methyl-1H-pyrazoles which were subsequently diazotized and coupled with malononitrile to yield a series of pyrazolylhydrazonomalononitriles. These compounds were then reacted with hydrazine monohydrate to provide, heterocyclic dyes, which were further diazotized and coupled with 4-hexylbenzene-1,3-diol to produce novel heterocyclic tetraazo dyes which were characterized by elemental analysis and spectral methods. The antimicrobial activity and absorption characteristics of the dyes were also examined in detail.

3_1_44_50_800


Keywords


Pyrazole; Solvatochromism; Heterocyclic dyes; Antimicrobial activity; 3-Aminocrotononitrile; 4-Hexylbenzene-1,3-diol

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.3.1.44-50.517

Article Metrics


This Abstract was viewed 685 times | PDF Article downloaded 892 times

Citations

/


[1]. H.M. Patel, D.P. Rajani, M.G. Sharma, H.G. Bhatt
Synthesis, Molecular Docking and Biological Evaluation of Mannich Products Based on Thiophene Nucleus using Ionic Liquid
Letters in Drug Design & Discovery  16(2), 119, 2018
DOI: 10.2174/1570180815666180502123743
/


[2]. Ş.Güniz Küçükgüzel, Sevil Şenkardeş
Recent advances in bioactive pyrazoles
European Journal of Medicinal Chemistry  97, 786, 2015
DOI: 10.1016/j.ejmech.2014.11.059
/


[3]. Javad Mokhtari, Bahareh Babaii, Abolfath Akbarzadeh, Parnian Ferdowsi
Synthesis and evaluation of novel antibacterial monoazo disperse dyes based on sulfonamide derivatives on polyester
Pigment & Resin Technology  46(6), 440, 2017
DOI: 10.1108/PRT-10-2016-0093
/


References

[1]. Elnagdi, M. H.; Sallam, M. M. M; Fahmy, H. M.; Ibrahim, S. A. M.; Elias, M. A. M. Helv. Chim. Acta 1976, 59(2), 551-557.
http://dx.doi.org/10.1002/hlca.19760590220

[2]. Elnagdi, M. H.; Elgemeie, G. E. H.; Abdelaal, F. A. E. Heterocycles 1985, 23(12), 3121-3153.
http://dx.doi.org/10.3987/R-1985-12-3121

[3]. Freeman, F. Synthesis-Stuttgart 1981, 12, 925-954.
http://dx.doi.org/10.1055/s-1981-29653

[4]. Tominaga, Y.; Honkawa, Y.; Hara, M.; Hosomi, A. J. Heterocycl. Chem. 1990, 27(3), 775-783.
http://dx.doi.org/10.1002/jhet.5570270355

[5]. Mohareb, R. M.; Sherif, S. M.; Gaber, H. M.; Ghabrial, S. S.; Aziz, S. I. Hetero. Chem. 2004, 15(1), 15-20.
http://dx.doi.org/10.1002/hc.10205

[6]. Hanefeld, U.; Rees, C. W.; White, A. J. P.; Williams, D. J. J. Chem. Soc. Perkin Trans. 1996, 13, 1545-1552.

[7]. Ho, Y. W. Dyes Pigm. 2005, 64(3), 223-230.
http://dx.doi.org/10.1016/j.dyepig.2004.06.007

[8]. Karcı, F.; Demirçalı, A. Dyes Pigm. 2007, 74(2), 288-297.
http://dx.doi.org/10.1016/j.dyepig.2006.02.007

[9]. Elagamey, A. G. A.; Mohamed, F.; Eltaweel, A. A. J. Prak. Chem. 1991, 333(2), 333-338.
http://dx.doi.org/10.1002/prac.19913330220

[10]. Karcı, F.; Sener, I.; Demircalı, A.; Burukoglu, N. Color. Technol. 2006, 122, 264-269.
http://dx.doi.org/10.1111/j.1478-4408.2006.00035.x

[11]. Karcı, F.; Karcı, F. Dyes Pigm. 2008, 76(1), 97-103.
http://dx.doi.org/10.1016/j.dyepig.2006.08.011

[12]. Karcı, F.; Demircalı, A.; Karcı, F.; Kara, I.; Ucun, F. J. Mol. Struct. 2009, 935(1-3), 19-26.
http://dx.doi.org/10.1016/j.molstruc.2009.06.040

[13]. Senga, K.; Novinson, T.; Springer, R. H.; Rao, R. P.; Obrian, D. E.; Robins, R. K. J. Med. Chem. 1975, 18(3), 312-314.
http://dx.doi.org/10.1021/jm00237a021
PMid:1094116

[14]. Dias, L. R. S.; Alvim, M. J.; Freitas, A. C. C.; Barreiro, E. J.; Miranda, A. L. P. Pharm. Acta Helv. 1994, 69(3), 163-169.
http://dx.doi.org/10.1016/0031-6865(94)90019-1

[15]. Lyga, J. W.; Patera, R. M.; Plummer, M. J.; Halling, B. P.; Yuhas, D. A. Pestic. Sci. 1994, 42(1), 29-36.
http://dx.doi.org/10.1002/ps.2780420106

[16]. Genin, M. J.; Biles, C.; Keiser, B. J.; Poppe, S. M.; Swaney, S. M.; Tarpley, W. G. J. Med. Chem. 2000, 43(5), 1034-1040.
http://dx.doi.org/10.1021/jm990383f
PMid:10715167

[17]. Ertan, N. Dyes Pigm. 1999, 44(1), 41-48.
http://dx.doi.org/10.1016/S0143-7208(99)00066-2

[18]. Tsai, P. C.; Wang, I. J. Dyes Pigm. 2005, 64(3), 259-264.
http://dx.doi.org/10.1016/j.dyepig.2004.05.013

[19]. Penchev, A.; Simov, D.; Gadjev, N. Dyes Pigm. 1991, 16(1), 77-81.
http://dx.doi.org/10.1016/0143-7208(91)87022-F

[20]. Sokolwska-Gajda, J. Dyes Pigm. 1991, 15(4), 239-245.
http://dx.doi.org/10.1016/0143-7208(91)80008-W

[21]. Sokolwska-Gajda, J. Dyes Pigm. 1992, 19(2), 149-156.
http://dx.doi.org/10.1016/0143-7208(92)87019-W

[22]. Yen, M. S.; Wang, I. J. Dyes Pigm. 2004, 62(2), 173-180.
http://dx.doi.org/10.1016/j.dyepig.2003.11.018

[23]. Yen, M. S.; Wang, I. J. Dyes Pigm. 2004, 63(1), 1-9.
http://dx.doi.org/10.1016/j.dyepig.2003.12.011

[24]. Desai, C. K.; Desai, K. R. High Perform. Polym. 2000, 12, 315-322.
http://dx.doi.org/10.1088/0954-0083/12/2/306

[25]. Wilkinson, S. C.; Higham, S. M.; Ingram, G. S.; Edgar, W. M. Adv. Dent. Res. 1997, 11, 515-522.
http://dx.doi.org/10.1177/08959374970110042001
PMid:9470512

[26]. Singha, K.; Singha, S.; Taylor, J. A. Dyes Pigm. 2002, 54, 189-196.
http://dx.doi.org/10.1016/S0143-7208(02)00053-0

[27]. Koneman, E. W.; Allen, S. D.; Winn, W. C. Colour atlas and textbook of diagnostic microbiology, Philadelphia, Lippincott Raven Publishers, 1997, 822-824.

[28]. Karcı, F.; Karcı, F. Dyes Pigm. 2008, 76(1), 147-157.
http://dx.doi.org/10.1016/j.dyepig.2006.07.029

[29]. Karcı, F.; Ertan, N. Dyes Pigm. 2002, 55(2-3), 99-108.
http://dx.doi.org/10.1016/S0143-7208(02)00102-X

[30]. Karcı, F. Color. Technol. 2005, 121(5), 275-280.
http://dx.doi.org/10.1111/j.1478-4408.2005.tb00286.x

[31]. Ozturk, A. Abdullah M.I. Sci. Total Environ. 2006, 358 (1-3), 137-142.
http://dx.doi.org/10.1016/j.scitotenv.2005.08.004
PMid:16165191

[32]. Liu, S.; Ma, J.; Zhao, D. Dyes Pigm. 2007, 75(2), 255-262.
http://dx.doi.org/10.1016/j.dyepig.2006.05.004

[33]. Odabasoglu, M.; Albayrak, C.; Ozkanca, R.; Akyan, F. Z.; Lonecke, P. J. Mol. Struct. 2007, 840(1-3), 71-89.
http://dx.doi.org/10.1016/j.molstruc.2006.11.025

[34]. Seferoglu, Z.; Ertan, N.; Yılmaz, E.; Uraz, G. Color. Technol. 2008, 24(1), 27-35.
http://dx.doi.org/10.1111/j.1478-4408.2007.00117.x

[35]. Liu, J.; Sun, G. Dyes Pigm. 2008, 77(2), 380-386.
http://dx.doi.org/10.1016/j.dyepig.2007.06.009

[36]. Shindy, H. A.; El-Maghraby, M. A.; Eissa, F. M. Dyes Pigm. 2006, 70(2), 110-116.
http://dx.doi.org/10.1016/j.dyepig.2005.04.003

[37]. Abd El-Aal, R. M.; Younis, M. Dyes Pigm. 2004, 60(3), 205-214.
http://dx.doi.org/10.1016/S0143-7208(03)00131-1


How to cite


Patel, H. Eur. J. Chem. 2012, 3(1), 44-50. doi:10.5155/eurjchem.3.1.44-50.517
Patel, H. Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol. Eur. J. Chem. 2012, 3(1), 44-50. doi:10.5155/eurjchem.3.1.44-50.517
Patel, H. (2012). Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol. European Journal of Chemistry, 3(1), 44-50. doi:10.5155/eurjchem.3.1.44-50.517
Patel, Hitendra. "Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol." European Journal of Chemistry [Online], 3.1 (2012): 44-50. Web. 23 Oct. 2019
Patel, Hitendra. "Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol" European Journal of Chemistry [Online], Volume 3 Number 1 (31 March 2012)

DOI Link: https://doi.org/10.5155/eurjchem.3.1.44-50.517

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.