Studies on Synthesis of Aldimines: Part-III. Synthesis, Spectral Characterization and Bioactivity of Salicylaldimines

Authors

  • C. J. Patil Organic Research Laboratory, Department of Chemistry, Smt. G. G. Khadse College, Muktainagar-425 306, (MS), India
  • Manisha C. Patil Dr. A. G. D. Bendale Mahila College, Jalgaon-425 001, (MS), India
  • Mrunmayee C. Patil Department of Pharmaceutical Science and Technology, Nathalal Parekh Marg, Institute of Chemical Technology, Matunga, Mumbai-400 019, M.S., India

DOI:

https://doi.org/10.25081/rrst.2019.11.5270

Keywords:

Imine, Aldimine or Azomethine, Salicylaldehyde, TLC and biological activity

Abstract

Compounds containing >C=N- (azomethine) were prepared from Salicylaldehyde with Aniline derivatives by conventional chemical synthesis method. The products are tested in process and the completion of reaction product formation was ascertained by TLC. The final products were characterized by physical viz. m.p., analytical viz. TLC, Instrumental viz. UV-Vis and FTIR spectral techniques. Results showed that all the marked activity coefficients(biopotential) for the studied compounds are less than the standard drug, Ketoconazole.

Downloads

Download data is not yet available.

References

1) Schiff H. Mittheilungen aus dem Universitätslaboratorium in Pisa: eine neue Reihe organischer Basen. Justus Liebigs Annalen der Chemie. 1864;131(1):118-9.
2) Uchida M, Tabusa F, Komatsu M, Morita S, Kanbe T and Nakagawa K, Studies on 2 (1H)-quinolinone derivatives as gastric antiulcer active agents. Synthesis and antiulcer activities of optically active alpha-amino acid derivatives of 2(1H)-quinolinone and oxindole, J. Chem. Pharm. Bull. (Tokyo). 1987;35(2):853-856.
3) a) Da Silva CM, Da Silva DL, Modolo LV, Alves RB, De Resende MA, Martins CB, de Fatima A, J. Adv. Res., 2011; 2: 1-8, Schiff bases: A short review of their antimicrobial activities. b) George RS, Joseph R, George KE, Int. J. Poly. Matter, 1993; 23: 17-26, Study of Polyschiff's Base as a Protective Agent in Natural Rubber.
4) Hussain Z, Yousif E, Ahmed A and Altaie A, Org. Med. Chem. Lett., 2014; 4: 1.
5) Bhat MA, Al-Omar MA, Siddiqui N. Antimicrobial activity of Schiff bases of coumarin-incorporated 1, 3, 4-oxadiazole derivatives: an in vitro evaluation. Medicinal Chemistry Research. 2013;22(9):4455-8.
6) Cimerman Z, Miljani? S, Gali? N. Schiff bases derived from aminopyridines as spectrofluorimetric analytical reagents. Croatica Chemica Acta. 2000 Feb 1;73(1):81-95.
7) (a) Kuehne ME, The Application of Enamines to a New Synthesis of ?-Ketonitriles, J. Am. Chem. Soc., 1959; 81(20): 5400-5404; (b) Westheimer FH, Taguchi K, Catalysis by molecular sieves in the preparation of ketimines and enamines, J. Org. Chem., 1971; 36: 1570, DOI: 10.1021/jo00810a033.
8) White WA, Weingarten H, A versatile new enamine synthesis, J. Org. Chem., 1967; 32(2): 213.
9) Abdel-Latif SA, Hassib HB, Issa YM, Studies on some salicylaldehyde Schiff base derivatives and their complexes with Cr(III), Mn(II), Fe(III), Ni(II) and Cu(II), Spectrochim. Acta., Part A: Mole. Biom. Spec., 2007; 67(3–4): 950–957.
10) Kumar S, Dhar DN, Saxena PN, Applications of metal complexes of Schiff bases – a review. J. Sci. Ind. Res., 2009; 68: 181–187.
11) Clougherty LE, Sousa JH, Wyman GM, Notes >C=N-Stretching Frequency in Infrared Spectra of Aromatic Azomethines, J. Org. Chem., 1956; 22: 462.
12) Patil CJ, Madhava AS, Ramachandriah G and Vyas DN, Electrochemical Studies of Schiff Bases: Part-2. Voltammetric Studies of Schiff Bases, Bull. Electrochem., 1993; 9 (2&3): 95.
13) Patil CJ, Madhava AS, Ramachandriah G and Vyas DN, Electrochemical Studies of Schiff Bases: Part-3. Electrometric Studies of the Reduction of Azomethine Bond of Schiff Bases and Effect of Substituent on it, Ind. J. Chem., 1994; 34A: 1037.
14) Patil CJ, Madhava AS, Ramachandriah G and Vyas DN, Electrochemical Studies of Schiff Bases: Part-5. Electrometric Studies of the Reduction of Azomethine Bond of Schiff Bases and Effect of Substituent on it, Bull. Electrochem., 1997; 13(8-9): 370.
15) Madhava AS, Patil CJ, Ramachandriah G and Vyas DN, Electrochemical Studies of Schiff Bases: Part-1. Electrochemical Studies of Schiff Bases, Bull. Electrochem., 1991; 7(6): 283.
16) Madhava AS, Patil CJ, Ramachandriah G and Vyas DN, Electrochemical Studies of Schiff Base Complexes: Part-1. Electrochemical Studies of Cd(II) Schiff Base Complexes, Bull. Electrochem., 1996; 12(5-6): 355.
17) Madhava AS, Patil CJ, Ramachandriah G and Vyas DN, Electrochemical Studies of Schiff Base Complexes: Part-2. Electrochemical Studies of Ni(II) Schiff Base Complexes, Bull. Electrochem., 1995; 11(9): 442.
18) Balamurugan V, Sankar S, Synthesis, Characterization and Biological Studies of Ni(II) and Zn(II) complexes with N,N’-Bis(Benzoin)-1,4-butane diamines, Int. J. Pharm. Pharm. Sci., 2014; 6(1): 758-761.
19) Rudbari HA, Iravani MR, Moazam V, Synthesis, characterization, X-ray crystal structures and antibacterial activities of Schiff base ligands derived from allylamine and their vanadium(IV), cobalt(III), nickel(II), copper(II), zinc(II) and palladium(II) complexes, J. Mol. Stru., 2016; 1125; 113–120.
20) Akbolat N, Yildiz A, Temel H, Ilhan S, Gul K, Antifungal studies of some metal complexes with Schiff base ligands, DUFED., 2012; 1(1): 15-22.
21) Patil CJ, Nehete CA and Mahajan HA, Azomethines and Biological Screening Part-1: An approach towards green sustainable chemistry by environmental friendly grindstone method compared with conventional method and screening of the Benzylideneanilines, Int. J. Green Herbal Chem., 2013; 2(2): 241-246.
22) Syam S, Abdelwahab SI, Al-Mamray MA and Mohan S, Synthesis of Chalcones with Anticancer Activities, Molecules, 2012, 17, 6179-6195.
23) Patil CJ, Patil Manisha C, Patil Mrunmayee C, Studies on Synthesis of Aldimines: Part-I. Synthesis, Characterization and Biological Activity of Aldimines from Benzaldehyde with Substituted anilines, Rec. Res. Sci. Techn., 2018; 10: 23-27.
24) Patil CJ, Patil MC and Nehete CA, Studies on Synthesis of Aldimines: Part-II. Comparison of the Products of conventional and Green Chemical Synthesis and Biological Activity Evaluation, Int. J. Green Herbal Chem., 2018; 2(2): 335-342 and ref. therein.
25) Kolate SS, Waghulde GP, Patil CJ, Sarode CH, Waghulde VS, Patil NK, Chaudhari SP and Patil PJ, Studies on Synthesis of Aldimines: Part-III. Synthesis, Spectral Characterization and Biological Activity of Salicylideneaniline Derivatives. Research Journey, Int. Multidisc. E-Res. J. 2017; 20: 49-54.
26) Patil CJ, Patil Manisha C, Patil Mrunmayee C, Studies on Synthesis of Aromatic Schiff Bases: Part-II. Synthesis, Characterization and Biological Evaluation of Ketimines from Benzophenone with Substituted-anilines, Acta Velit., 2017; 3(3): 52-59 and ref. therein.

Published

08-06-2020

How to Cite

Patil, C. J., Patil, M. C., & Patil, M. C. (2020). Studies on Synthesis of Aldimines: Part-III. Synthesis, Spectral Characterization and Bioactivity of Salicylaldimines. Recent Research in Science and Technology, 11(1). https://doi.org/10.25081/rrst.2019.11.5270

Issue

Section

Articles