Synthesis, Characterization and Keto-Enol Tautomerism of Novel 2-(Trifluoromethyl)benzohydrazide Derivatives

Ramesh Navudu; Gangadhara Rao Mannem; Hari Babu Bollikolla

doi:10.14233/ajchem.2016.19703

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Issue Published : February 29, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Characterization and Keto-Enol Tautomerism of Novel 2-(Trifluoromethyl)benzohydrazide Derivatives

https://doi.org/10.14233/ajchem.2016.19703

Ramesh Navudu

Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar-522 510, India

Gangadhara Rao Mannem

Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar-522 510, India

Hari Babu Bollikolla

Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar-522 510, India

Corresponding Author(s) : Hari Babu Bollikolla

dr.b.haribabu@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 6 (2016): Vol 28 Issue 6
Article Published : February 29, 2016

Abstract

A series of novel 2-(trifluoromethyl)benzohydrazide derivatives were synthesized starting from 2,2,2-trifluoromethyl benzoic acid in three consecutive steps by using hydrazine hydride and aldehydes at room temperature. In above methodology a total of 21 novel benzohydrazide derivatives (4a-4u) were produced. The proton NMR spectra revealed that all the 2-(trifluoromethyl)benzohydrazide derivatives were showed keto-enol tautomerism. An observation on the keto-enol ratios of various substituents, provided that compounds having electron withdrawing groups gives high enol form compared to the donating groups.

Keywords

2,2,2-Trifluoromethyl benzoic acid Arylaldehydes Benzohydrazide derivatives Keto-enol tautomerism

Navudu, R., Mannem, G. R., & Bollikolla, H. B. (2016). Synthesis, Characterization and Keto-Enol Tautomerism of Novel 2-(Trifluoromethyl)benzohydrazide Derivatives. Asian Journal of Chemistry, 28(6), 1351–1360. https://doi.org/10.14233/ajchem.2016.19703

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References

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References

A.P. Rajput and S.S. Rajput, Int. J. Pharm. Pharm. Sci., 3, 346 (2011).

R. Kalsi, M. Shrimali, T.N. Bhalla and J.P. Barthwal, Indian J. Pharm. Sci., 41, 353 (2006).

Y.S. Rao, I. Aminul, D. Nageswar and B.H. Babu, Indian J. Chem., 54B, 1162 (2015).

Y. Janin, Bioorg. Med. Chem., 15, 2479 (2007); doi:10.1016/j.bmc.2007.01.030.

S.R. Yatcherla, A. Islam, D. Nageswar and B.H. Babu, Asian J. Chem., 27, 3729 (2015); doi:10.14233/ajchem.2015.18945.

E. Gürsoy and N.U. Güzeldemirci, Eur. J. Med. Chem., 42, 320 (2007); doi:10.1016/j.ejmech.2006.10.012.

Y.S. Rao, I. Aminul, D. Nageswar and B.H. Babu, Int. J. Curr. Res. Chem. Pharma. Sci., 2, 25 (2015).

L. Savini, L. Chiasserini, V. Travagli, C. Pellerano, E. Novellino, S. Cosentino and M.B. Pisano, Eur. J. Med. Chem., 39, 113 (2004); doi:10.1016/j.ejmech.2003.09.012.

S. Sundriyal, R.K. Sharma and R. Jain, Curr. Med. Chem., 13, 1321 (2006); doi:10.2174/092986706776873023.

T.R. Li, Z.Y. Yang and B.D. Wang, Chem. Pharm. Bull. (Tokyo), 55, 26 (2007); doi:10.1248/cpb.55.26.

G. Sammaiah and M. Sarangapani, Asian J. Chem., 20, 282 (2008).

G. Sammaiah and M. Sarangapani, Int. J. Chem. Sci., 6, 503 (2008).

G. Sammaiah and M. Sarangapani, Int. J. Chem. Sci., 5, 181 (2007).

C.G. Wermuth, J. Med. Chem., 47, 1303 (2004); doi:10.1021/jm030480f.

G. Kumar, D. Kumar, S. Devi, R. Johari and C.P. Singh, Eur. J. Med. Chem., 45, 3056 (2010); doi:10.1016/j.ejmech.2010.03.036.

S. Gemma, G. Kukreja, C. Fattorusso, M. Persico, M. Romano, M. Altarelli, L. Savini, G. Campiani, E. Fattorusso, N. Basilico, D. Taramelli, V. Yardley and S. Butini, Bioorg. Med. Chem. Lett., 16, 5384 (2006); doi:10.1016/j.bmcl.2006.07.060.

P. Singh and P.K. Jangra, Der Chemica Sinica, 1, 118 (2010).

V. Singh, V.K. Srivastava, G. Palit and K. Shanker, Arzneim-Forsch. Drug Res., 42, 993 (1992).

G. Turan-Zitouni, M.F. Sivaci, S. Kilic and K. Erol, Eur. J. Med. Chem., 36, 685 (2001); doi:10.1016/S0223-5234(01)01252-1.

O. Bekircan, M. Küxük, B. Kahveci and S. Kolayli, Arch. Pharm., 338, 365 (2005); doi:10.1002/ardp.200400964.

B.E. Gilbert and V. Knight, Antimicrob. Agents Chemother., 30, 201 (1986); doi:10.1128/AAC.30.2.201.

K. Akiba and M. Wada, Chem. Abstr., 111, 96964b (1989).

N. Ramalakshmi, R. Vijayakumar, K. Ilango, S. Arunkumar and A. Puratchikody, Int. J. Chem. Sci., 6, 1213 (2008).

S.D. Young, S.F. Britcher, L.O. Tran, L.S. Payne, W.C. Lumma, T.A. Lyle, J.R. Huff, P.S. Anderson, D.B. Olsen and S.S. Carroll, Antimicrob. Agents Chemother., 39, 2602 (1995); doi:10.1128/AAC.39.12.2602.

B.D. Roth, Prog. Med. Chem., 40, 1 (2002); doi:10.1016/S0079-6468(08)70080-8.

K.-H. Ahn, H. Kim, J.R. Kim, S.C. Jeong, T.S. Kang, H.T. Shin and G.J. Lim, Bull. Korean Chem. Soc., 23, 626 (2002); doi:10.5012/bkcs.2002.23.4.626.

D.T. Wong, J.S. Horng, F.P. Bymaster, K.L. Hauser and B.B. Molloy, Life Sci., 15, 471 (1974); doi:10.1016/0024-3205(74)90345-2.

P. Schlagenhauf, Travel Med., 6, 122 (1999); doi:10.1111/j.1708-8305.1999.tb00843.x.

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Synthesis, Characterization and Keto-Enol Tautomerism of Novel 2-(Trifluoromethyl)benzohydrazide Derivatives

Corresponding Author(s) : Hari Babu Bollikolla

Abstract

Keywords

Full Article

Download Citation

References

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