Dichlofenac (2-[(2,6-Dichloroanilino)Phenyl]Acetic Acid) As A Precursor To New Heterocyclic Compounds
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.
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.
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.
Details
| Primary Language | English |
|---|---|
| Subjects | Engineering |
| Journal Section | Articles |
| Authors | |
| Publication Date | December 4, 2018 |
| Published in Issue | Year 2018Issue: 4 |
