MICROWAVE ASSISTED SYNTHESIS, SPECTRAL CORRELATION AND ANTIMICROBIAL EVALUATION OF SOME ARYL IMINES
- Solvent-free synthesis,
- SiO2-H3PO4,
- Aryl imines,
- IR and NMR spectra,
- Spectral correlation study
- Antimicrobial activities ...More
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Abstract
A series of aryl imines have been synthesized by SiO2-H3PO4 catalyzed microwave assisted condensation of amine and aldehyde under solvent-free conditions. The yield of the imines has been found to be more than 80%. The purity of all imines has been checked using their physical constants and spectral data as published earlier in literature. The UV λmax(nm), infrared νC=N(cm-1), NMR δ(ppm) of C-H and C=N spectral data have been correlated with Hammett substituent constants and F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effect of substituents on the above spectral data has been studied. The antimicrobial activities of all imines have been studied using Bauer-Kirby method.
References
- A. S. Shawali, N. M. S. Harb, K. O. Badahdah, J. Heterocycl.Chem. 22, 1397 (1985).
- M. Mustapha, B. R. Thorat, S.Sawant, R. G. Atram, R. Yamgar, J. Chem. Pharm. Res. 3(4), 5 (2011).
- K. C. Gupta, A. K. Sutar. Co. ord. Chem. Rev. 252, 1420 (2008).
- M. Yuan, F. Zhao, W. Zhang, Z. M. Wang, S. Gao, Inorg. Chem. 46, 11235 (2007).
- H. Fukuda, K. Amimoto, H. Koyama, T. Kawato, Tetrahedron Lett. 50, 5376 (2009).
- Y.C. Liu, C.Y. Yang, Inorg. Chem. Commun., 12, 704 (2009).
- A. C. W. Leung, M. J. Mac Lachlan, J. Inorg. Organomet.Polym.Mater. 17, 57 (2007).
- W. Zishen, L. Zhiping, Y. Zhenhuan Transit. Met. Chem. 18 291 (1993).
- K. Nejati, Z. Rezvani, B. Massoumi, Dyes Pigment. 75 653 (2007).
- E. Naderi, A. H. Jafari, M. Ehteshamzadeh, M.G. Hosseini, Met. Chem. Phys. 115 852 (2006).
- D. Sriram, P. Yogeeswari, N.S. Myneedu, V. Saraswati, Bioorg. Med. Chem. Lett. 16, 2127 (2006).
- V. Stilinovic, D. Cincic, B. Kaitner, Acta. Chim.Slov. 55, 874 (2008).
- V. Tiwari, J. Meshram, P. Ali, Der. Pharm. Chim. 2, 187 (2010).
- J.J. Bhatt, B.R. Shah, H.P. Shah, P.B. Trivedi, N.K. Undavia, N.C. Desai, Indian. J. Chem. 33B, 189 (1994).
- A. A. Bakibaev, V. K. Gorshkova, O. V. Arbit, V. D. Filimonov, A. S. Saratikov, Pharm. Chem. J. 31, 53 (1997).
- R.B. Patel, P.S. Desai, K.R. Desai, K.H. Chikhalia, Indian J. Chem. 45B, 773 (2006).
- S. Kantevari, T. Yempala, P. Yogeswari, D. Sriram, B. Sridhar, Bioorg. Med. Chem. Lett. 15, 4316 (2011).
- A. Kundu, N. A. Shakil, D. B. Saxena, J. Pankaj Kumar and S. Walia, J. Env. Sci. Health. 44B 428 (2000).
- R. Yadav, S.D. Srivastava, S.K. Srivastava, Indian. J. Chem. 44B, 1262 (2005).
- R. T. McBurney, P. C. Fernando, J. C. Walton, RSC Adv. 12, 1264 (2012).
- M. Adib, E. Sheibani, H. R. Bijanzadeh, L. G. Zhu, Tetrahedron. 64, 10681 (2008).
- A. K. Chakraborti, S. Bhagat, S. Rudrawar, Tetrahedron Lett. 45, 7641 (2004).
- M. Movrin, D. Maysinger, Pharmaize, 34, 535 (1979).
- J. Barluenga, J. A. Agustin, F. Aznar, C. Valdes, J. Am. Chem. Soc. 131, 4031 (2009).
- D. Bandyophayay, S. Mukherjee, R. R. Rodriguez, B. K. Banik. Molecules, 15, 4207 (2010).
- S. K. Samanta, I.Kylanlathi and J. Y. Kauhaluoma, Bioorg. Med. Chem. Lett. 15, 3717 (2005).
- A. Lumbroso, F. Chevillier, I. Beaudet, T. Bessan, E. L. Grognet, Tetrahedron. 65 9180 (2009).
- H. J. conn, “A Handbook on the Nature and Uses of the Dyes Employed in the Biological Laboratory” SIXTH EDITION, THE WILLIAMS & WILKINS COMPANY, Baltimore 2, (1953) Maryland, USA.
- B. D. Mather, K. Viswanathan, K. M. Miller, T. E. Long., Prog. Polym. Sci. 31, 487 (2006).
- S. F. Martin, Pure Appl. Chem. 81, 195(2009).
- A. C. Dash, B. Dash, D. Panda, J. Org. Chem. 50, 2905 (1985).
- J. H. Xie, S. F. Zhu, Q. L. Zhou, Chem. Rev. 111, 1731(2011).
- S. E. Denmark, G. L. Beutner, Angew. Chem. Int. Ed. 47, 1560 (2008).
- A. Suares, C. W. Downey, G. C. Fu, J. Am. Chem. Soc. 127, 11244 (2005).
- S. France, M. H. Shah, A. Weatherwax, H. Wack, J. P. Roth, T. Lectka, J. Am. Chem. Soc. 127, 1206 (2005).
- W. Chang, B. J. Ahn, J. Ind. Engg. Chem. 10, 690 (2004).
- M. Abid, M. Savolainen, S.Landge, J. Hu, G. K. Suryaprakash, G. A. Olah, B. Torok, J. Fluo. Chem. 128, 587 (2007).
- D. A. Barr, G. Donegn, R. Grigg, J. Chem. Soc., Perkin Trans. 1, 1550 (1989).
- L. Blackburn, R. J. K. Taylor, Org. Lett. 3, 1637 (2001).
- M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu, Res. Chem. Inter. med. 33, 541 (2007).
- R. S. Varama, Green Chem. (1999) 43.
- G. Dutheuil, S. C. Bonnaire, X. Pannecoucke, Angew. Chem. Int. Ed. Engl .46, 1290 (2007).
- B. H. Lipshutz, H. Shimizu, Angew. Chem. Int. Ed. 43 2228 (2004).
- E. Ali, M. R. N. Jamal, Efficient synthesis of imines by MCM-41-SO3H nanaocatalyst. No. A006, 14th international Conference on synthetic organic chemistry, (ESCOC-14), 1 (2010).
- A. Hasaninejad, A. Zare, H. Sharghi, M. Shekouhy, Arkicov. 11, 64 (2008).
- H. Zhanag, S. Syed, C. F. Barbas, Org. Lett. 12,708 (2010).
- C. M. Bode, A. Ting, S. E. A. Schaus, Tetrahedron. 62, 11499 (2006).
- M. A. Vazquez, M. Landa, L. Reyes, M. J. Tamariz, D. Francisco, Synth. Commun. 34, 2705 (2004).
- M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph series, ACS, Washington, DC, (1990).
- S. M. Landge, V. Atanassova, M.Thimmaiah, B. Torok, Tetrahedron Lett. 48, 5161 (2007).
- G. Thirunarayanan, .Iup. J. Chem. 3(4), 35 (2010).
- A. W. Bauer, W. M. M. Kirby, J. C Sherris, M. Truck, .Am. J. Clin. Pathol. 45, 493 (1996).
- K. Sathiyamoorthi, V. Mala, S.P. Sakthinathan, D. Kamalakkannan, R. Suresh, G. Vanangamudi , G. Thirunarayanan Spectrochimica Acta, 112A, 245 (2013).
- (a). S. P. Sakthinathan, G. Vanangamudi, G. Thirunarayanan Spectrochimica Acta 95A, 693 (2012). (b). G. Thirunarayanan, G. Vanangamudi, Spectrochimica Acta 81A, 390 (2011). (c) G. Thirunarayanan, M. Gopalakrishnan, G.Vanangamudi, Spectrochimica Acta 67(A), 1106 (2007).
- B.Zˇ. Jovanovic´, A.D. Marinkovic´, F.H. Assaleh, J. Csana´d, J. Mol. Str. 744 (2005).
- S. Ž. Drmanić, A. D. Marinković, J. B. Nikolić, B. Jovanović, J. Serb. Chem. Soci. 77, 1 (2012).
- C. G. Swain, E. C. Lupton, J.Amer. Chem. Soc., 90, 4328 (1968).