European Journal of Chemistry

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



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Abdulaziz Alnajjar
Marzouq Alsaiedi
Morsy Ahmed El-Apasery

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).

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Alnajjar, A.; Alsaiedi, M.; El-Apasery, M. A. An Efficient Route for the Synthesis of Some Monoazo Disperse Dyes Derived from Nicotinic Acid Derivatives. Eur. J. Chem. 2013, 4, 53-57.

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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

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The Public Authority for Applied Education and Training (Transform grant TS-07-11) of Kuwait.
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