European Journal of Chemistry 2013, 4(1), 53-57. doi:10.5155/eurjchem.4.1.53-57.733

An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives


Abdulaziz Alnajjar (1) , Marzouq Alsaiedi (2) , Morsy Ahmed El-Apasery (3,*)

(1) Applied Science Department, College of Technological Studies, Public Authority for Applied Education and Training, Safat, 70654, Kuwait
(2) Applied Science Department, College of Technological Studies, Public Authority for Applied Education and Training, Safat, 70654, Kuwait
(3) Dyeing, Printing and Textile Auxiliaries Department, Textile Research Division, National Research Centre, 12622 Dokki, Giza, Egypt
(*) Corresponding Author

Received: 03 Jan 2013, Accepted: 05 Feb 2013, Published: 31 Mar 2013

Abstract


Ethyl 2-amino-3-cyano-4-phenylnicotinates (8), could be readily synthesized via reacting ethyl propiolate with benzylidenemalononitrile in the presence of L-proline as a catalyst and subsequent rearrangement of the so formed 2-aminopyran (7), with acetic acid in the presence of ammonium acetate. A series of 2-amino and 2-hydroxyarylazonicotinates monoazo disperse dyes (12a-c), were prepared in a good yields via condensation of arylhydrazonals (11a-c), with active methylene nitriles. The compound 9 was also characterized by single crystal X-ray diffraction studies. Crystal data for compound 9, C15H18O6 (M = 294.29): hexagonal, space group P65 (no. 170), a = 11.3311(5) Å, c = 19.5375(10) Å, V = 2172.42(18) Å3, Z = 6, T = 296(2) K, μ(MoKα) = 0.879 mm-1, Dcalc = 1.350 g/mm3, 4546 reflections measured (9.02 ≤ 2Θ ≤ 132.96), 2271 unique (Rint = 0.0921) which were used in all calculations. The final R1 was 0.0686 (>2σ(I)) and wR2 was 0.1691 (all data).

4_1_53_57

Keywords


Enaminones; Nicotinic acid; Disperse dyes; Arylhydrazonals; Dye intermediates; Arylazonicotinates

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.4.1.53-57.733

Article Metrics


This Abstract was viewed 870 times | PDF Article downloaded 189 times

Citations

/


[1]. Morsy Ahmed El-Apasery, Samar Mohamed Ashkar, Marwan Touma, Mohamed Hilmy Elnagdi
A facile synthesis of some biologically active disperse dyes derived from arylazonicotinates and their application on polyester fabrics
European Journal of Chemistry  4(3), 245, 2013
DOI: 10.5155/eurjchem.4.3.245-249.820
/


[2]. Morsy Ahmed El-Apasery, Fawzia Al-Qalaf, Khaledah Almohammad, Huda Mahmoud
Synthesis of some biologically active monoazo disperse dyes derived from nicotinic acid derivatives under microwave irradiation for dyeing polyester fabrics
European Journal of Chemistry  4(3), 211, 2013
DOI: 10.5155/eurjchem.4.3.211-215.783
/


[3]. Saleh Mohammed Al-Mousawi, Morsy Ahmed El-Apasery, Mohamed Hilmy Elnagdi
Arylazoazines and arylazoazoles as interesting disperse dyes: Recent developments with emphasis on our contribution laboratory outcomes
European Journal of Chemistry  5(1), 192, 2014
DOI: 10.5155/eurjchem.5.1.192-200.883
/


References

[1]. Sayed, A. Z.; Aboul-Fetouh, M. S.; Nassar, H. S. J. Mol. Struct. 2012, 1010, 146-151.
http://dx.doi.org/10.1016/j.molstruc.2011.11.046

[2]. Gharanjig, K.; Sadeghi-Kiakhani, M.; Arami, M.; Mahmoodi, N. M.; Khosravi, A. Color. Technol. 2010, 126(1), 37-41.
http://dx.doi.org/10.1111/j.1478-4408.2010.00225.x

[3]. Suesat, J.; Mungmeechai, T.; Suwanruji, P.; Parasuk, W.; Taylor, J. A.; Phillips, D. A. S. Color. Technol. 2011, 127(4), 217-222.
http://dx.doi.org/10.1111/j.1478-4408.2011.00301.x

[4]. El-Apasery, M. A.; Al-Mousawi, S. M.; Mahmoud, H.; Elnagdi, M. H. Eur. J. Chem. 2011, 2(2), 168-172.
http://dx.doi.org/10.5155/eurjchem.2.2.168-172.228

[5]. Khalil, K.; Al-Matar, H.; Elnagdi, M. H. Eur. J. Chem. 2010, 1(4), 252-258.
http://dx.doi.org/10.5155/eurjchem.1.4.252-258.211

[6]. Behbehani, H.; Abdel-Khalik, M. M.; Elnagdi, M. H. Org. Prep. Proced. Int. 1999, 31(5), 551-557.
http://dx.doi.org/10.1080/00304949909355339

[7]. Al-Mousawi, S. M.; El-Apasery, M. A.; Mahmoud, H. M. Molecules 2012, 17, 11495-11506.
http://dx.doi.org/10.3390/molecules171011495
PMid:23018924

[8]. Al-Mousawi, S. M.; El-Apasery, M. A. Molecules 2012, 17, 6547-6556.
http://dx.doi.org/10.3390/molecules17066547
PMid:22728352

[9]. Al-Mousawi, S. M.; El-Apasery, M. A.; Mahmoud, H.; Elnagdi, M. H. Int. Res. J. Pure Appl. Chem. 2012, 2, 77-90.

[10]. Kim, K. R.; Rhee, S. D.; Kim, H. Y.; Jung, W. H.; Yang, S. D.; Kim, S. S.; Ahn, J. H.; Cheon, H. Eur. J. Pharm. 2005, 518(1), 63-70.
http://dx.doi.org/10.1016/j.ejphar.2005.05.030

[11]. Zaky, O. S.; Moustafa, M. S.; Selim, M. A.; El-Maghraby, A. M.; Elnagdi, M. H. Molecules 2012, 17(5), 5924-34.
http://dx.doi.org/10.3390/molecules17055924
PMid:22609783

[12]. Mohanta, G. P.; Manna, P. K.; Manavalan, R. Ind. J. Pharm. Sci. 2002, 64(5), 489-491.

[13]. El-Apasery, M. A.; Al-Mousawi, S. M.; Mahmoud, H.; Elnagdi, M. H. Int. Res. J. Pure Appl. Chem. 2011, 1, 69-93.

[14]. Bazhin, D. N.; Kudyakova, Y. S.; Burgart, Y. V.; Saloutin, V. I. Tetrahedron Lett. 2012, 53(15), 1961-1963.
http://dx.doi.org/10.1016/j.tetlet.2012.02.015

[15]. Elnagdi, N. M. H.; Al-Hokbany, N. S. Molecules 2012, 17, 4300-4312.
http://dx.doi.org/10.3390/molecules17044300
PMid:22491679


How to cite


Alnajjar, A.; Alsaiedi, M.; El-Apasery, M. Eur. J. Chem. 2013, 4(1), 53-57. doi:10.5155/eurjchem.4.1.53-57.733
Alnajjar, A.; Alsaiedi, M.; El-Apasery, M. An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives. Eur. J. Chem. 2013, 4(1), 53-57. doi:10.5155/eurjchem.4.1.53-57.733
Alnajjar, A., Alsaiedi, M., & El-Apasery, M. (2013). An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives. European Journal of Chemistry, 4(1), 53-57. doi:10.5155/eurjchem.4.1.53-57.733
Alnajjar, Abdulaziz, Marzouq Alsaiedi, & Morsy Ahmed El-Apasery. "An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives." European Journal of Chemistry [Online], 4.1 (2013): 53-57. Web. 23 Jan. 2019
Alnajjar, Abdulaziz, Alsaiedi, Marzouq, AND El-Apasery, Morsy. "An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives" European Journal of Chemistry [Online], Volume 4 Number 1 (31 March 2013)

DOI Link: https://doi.org/10.5155/eurjchem.4.1.53-57.733

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2018  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 2018 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.