Dichlofenac (2-[(2,6-Dichloroanilino)Phenyl]Acetic Acid) As A Precursor To New Heterocyclic Compounds

Mohammed A. Al-ıraqı; Ahmad W. Kasım

Research Article

Dichlofenac (2-[(2,6-Dichloroanilino)Phenyl]Acetic Acid) As A Precursor To New Heterocyclic Compounds

Year 2018, Issue: 4, 296 - 302, 04.12.2018

Mohammed A. Al-ıraqı Ahmad W. Kasım

Abstract

A
new series of five and six membered ring heterocyclic compounds were
synthesized using 2-[(2,6-dichloroanilino) phenyl] acetic acid (Dichlofenac)
(1) as starting material. This compound was converted to its ethyl ester
derivative (2) via the acid catalyzed esterification. The ester (2) was
converted to the hydrazide derivative (3) through its reaction with hydrazine
hydrate. The hydrazide (3) was used as precursor to synthesize the heterocycle
containing compounds. Moreover, the hydrazide (3) was converted to the
thiosemicarbazide derivatives (5-7) by their reaction with isothiacyanate
compounds. The compounds (5-7) were converted to five membered ring
heterocyclic compounds, such as, 1,3,4-triazols (8, 9, 12, 13),
1,3,4-thiadiazoles (10, 11) and 1,3,4-oxadiazol (14) under the influence of a
miscellaneous of reagents. The cabohydrazide (3) was incorporated in to
1,3,4-oxadiazol (4), phthalimido derivative (15), tetrazine
compound (17), pyrazolines (18-22) and isocyanate compound (24). All the
synthesized compounds were characterized by physical and spectral data.

Keywords

1-3-4 oxadiazole , 1-3-4 thiadiazole , 1-3-4 triazole , Tetrazine , Thiosemicarbazide

References

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Year 2018, Issue: 4, 296 - 302, 04.12.2018

Mohammed A. Al-ıraqı Ahmad W. Kasım

Abstract

References

A. Palomer, F. Cabre, J. Pascual, J. Campos, M.A. Trugillo, A. Entrena, M.A. Gallo, L. Garcia, D. Maclcon, and A. Espinosa, (2002), J. Med. Chem., 45, 1402-1411. S. Sivaraj, P. Muthumani, S. Venkataraman, J. Raamamurthy, R. Siva Kumar, and P. Kumarnallasivan, (2012), Der. Pharma. Chemica., 4(3), 1339-1349. M. Duflas, M.R. Norrison, J. Brelet, J. Courant, G. Le Baut, N. Grimaud and J. Petit, (2001), Eur. J. Med. Chem.,36, 545-553. A.S. Kalgutkar, A.B. Marnett, B.C. Crews, R.P. Remmel, and L.J. Marnett, (2000), J. Med. Chem. 43, 2860-2870. P. L. Somashekar, P. N. Sanjaypai and G. RAO, (2013), Chem. Sci. Trans., 2(3), 813-820. A. Hasan, N. F. Tomas and S. Gapil, (2011), Molecules, 16, 1297-1309. V. Padmavathi, G.S. Reddy, A.V. N. Mohan and K. Mahesh, (2008), Arkivock (xvii), 48-60. M. Amir and K. Shikha, (2004), Eur. J. Med. Chem., 39(6), 535-545. S. Hussain, J. Sharma and M. Amir, (2008), E-Journal of Chemistry, 5(4), 963-968. K.M. Daoud, A.W. Al-Obaydi,( 2008), National Journal of Chemistry, 31, 531-542. A.A. Abu-Hashem and A.S. Aly, (2012), Arch. Pharm. Res., 35(3), 437-445. M. A. El-Hashash and S. A. Rizk, (2012), Middle-East J. Sci. Res., 11(4), 541-549. J. Al-Hamadany and A. M. Hamdy, J. Edu. &Sci, 2(18), 42-50, (2006). V. Jakubkiene, Z. Kacnova, M. M. Burbuliene and P. Vainilavicius, (2010), Arkivoc, xi, 39-48. T. Sasaki, Sh. Eguchi and T. Okano, (1980), Synthesis, 472-475. R.M. Silverstein, (2005)” Spectrometric identification of organic compounds”.7th ed. John Wiley and Sons, Inc. New York. E. Pretch, (2009), ”Structure determination of organic compounds”, 4th ed. Springer - Verlag Berlin Heidelberg.

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Details

Primary Language	English
Subjects	Engineering
Journal Section	Articles
Authors	Mohammed A. Al-ıraqı Ahmad W. Kasım
Publication Date	December 4, 2018
Published in Issue	Year 2018 Issue: 4

Cite

APA	Al-ıraqı, M. A., & Kasım, A. W. (2018). Dichlofenac (2-[(2,6-Dichloroanilino)Phenyl]Acetic Acid) As A Precursor To New Heterocyclic Compounds. The Eurasia Proceedings of Science Technology Engineering and Mathematics(4), 296-302.