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Solvent-free synthesis and spectral linearity of some (E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2H cyclopenta[b]thiophene-3-carboxamides

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EN
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EN
Some (E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2H-cyclopenta[b]thiophene-3-carboxamide derivatives have been synthesized by SiO2:H3PO4 catalyzed solvent-free condensation of 2-amino-N-(3-chloro-4-fluorophenyl)-hexahydro-2H-cyclopenta [b]thiophene-3-carboxamide and various substituted benzaldehydes in microwave irradiation. The yield of the imine-carboximido derivatives has been found to be more than 85 %. The purity of all imine-carboximido derivatives has been checked using their physical constants and spectral data. The spectral data of the imine-carboximido derivatives such as infrared ? (cm-1) of CO, NH, C-N, C-Cl, C-F, C=N, and the NMR chemical shifts (?, ppm) of NH, CH, CO and C=N have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analysis, the effects of substituent on the above spectral group absorptions have been discussed.
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160--174
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Bibliogr. 72 poz., rys., tab., wykr.
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Bibliografia
  • [1] Lau K. Y., Mayr A., Cheung K. K., Inorg. Chim. Acta. 285 (1999) 223-225.
  • [2] Shawali A. S., Harb N. M. S., J. Heterocycl. Chem. 22 (1985) 1397-1403.
  • [3] Mustapha M., Thorat SudhirSawant B. R., Atram R. G., Yamgar R., J. Chem. Pharm. Res. 3(4) (2011) 5-9.
  • [4] Yamgar R., Kamat P., Khandekar D., Sawant S., J. Chem. Pharm. Res. 3 (2011) 188-198.
  • [5] Gupta K. C., Sutar A. K. Coord. Chem. Rev. 252 (2008)1420-1450.
  • [6] Yuan M., Zhao F., Zhang W., Wang Z. M., Gao S., Inorg. Chem. 46 (2007) 11235-11242.
  • [7] Fukuda H., Amimoto K., Koyama H., Kawato T. Tetrahedron Lett. 50 (2009) 5376-5378.
  • [8] Lee J. Y., Lee Y. M., Kotani H., Nam W., Fukuzumi S., Inorg. Chem. Commun. 12 (2009) 704-706.
  • [9] Leungs A. C. W., MacLachlan M. J., J. Inorg. Organomett. Poly. Mat. 17 (2007) 57-89.
  • [10] Zishen W., Zhiping L., Zhenhuan Y., Trans. Metal Chem. 18 (1993) 291-294.
  • [11] Netaji K., Rezvani Z., Massoumi B., Dyes and Pigments. 75 (2007) 653-657.
  • [12] Naderi E., Jafari A. H., Ehteshamzadeh M., Hosseini M. G., Mat. Chem. Phys. 115 (2006) 852-858.
  • [13] Sriram D., Yogeeswari P., Myneedu N. S., Saraswati, V., Bioorg. Med. Chem. Lett. 16 (2006) 2127-2129.
  • [14] Dusek M., Fejfarova K., Khalaji A. D., Acta Chim. Slov. 57 (2010) 257-261.
  • [15] Tiwari V., Meshram J., Ali P., Der Pharm. Chem.. 2 (2010) 187-195.
  • [16] Mistry, K.M., Desai, K.R., E-J. Chem. 1 (2004) 189-193.
  • [17] Sayyed M., Mokle S., Bokhare M., Mankar A., Bhusare S., Vibhute Y., Arkivoc. 2 (2006) 187-192.
  • [18] Bakibaev A. A., Gorshkova V. K., Saratikov A. S., Pharm. Chem. J. 31 (1997) 53-67.
  • [19] Patel R. B., Desai P. S., Desai K. R., Chikhalia K. H., Indian J. Chem. 45B (2006) 773-778.
  • [20] Kantevari S., Yempala T., Yogeeswari P., Sriram D., Sridhar B., Bioorg. Med. Chem. Lett. 2 (2011) 4316-4319.
  • [21] Kundu A., Shakil N. A., Saxena D. B., Pankaj Kumar J., Walia S., J. Environ. Sci. Health. 44B (2000) 428-434.
  • [22] Yadav R., Srivastava S. D., Srivastava S. K., Indian J. Chem. 44B (2005) 1262-1265.
  • [23] McBurney R. T., Fernando P. C., Walton J. C., Royal Society of Chemistry Advances. 12 (2012) 11264-1274.
  • [24] Nagendrappa G., Resonance. (2002) 59-68.
  • [25] Adib M., Sheibani E., Bijanzadeh H. R., Zhu L. G., Tetrahedron 64 (2008) 10681-10686.
  • [26] Chakraborti A. K., Bhagat S., Rudrawar S., Tetrahedron Lett. 45 (2004)7641-7644.
  • [27] Weintraub P. M., Sabol J. S., Kane J. M., Borcherding D. R., Tetrahedron. 59 (2003) 2953-2989.
  • [28] Movrin M., Maysinger D., Pharmaize 34 (1979) 535-536.
  • [29] Barluenga J., Agustin J. A., Aznar F., Valdes C., J. Am. Chem. Soc. 131 (2009) 4031-4041.
  • [30] Bandyophayay D., Mukherjee S., Rodriguez R. R., Banik B. K., Molecules, 15 (2010) 4207-4212.
  • [31] Samanta S. K., Kylanlathi I., Kauhaluoma J. Y., Bioorg. Med. Chem. Lett. 15 (2005) 3717-3719.
  • [32] Conn H. J., 1953. A Handbook on the Nature and Uses of the Dyes Employed in the Biological Laboratory” Sixth Edition, The Williams & Wilkins Company, Baltimore- 2, Maryland, USA.
  • [33] Mather B. D., Viswanathan K., Miller K. M., Long T. E., Prog. Poly. Sci. 31 (2006) 487-531.
  • [34] Martin, S. F., Pure Appl. Chem. 81 (2009) 195-204.
  • [35] Dash A. C., Dash B., Panda D., J. Org. Chem. 50 (1985) 2905-2910.
  • [36] Bergbreiter D. E., Newcombe M., 1983. Asymmetric Synthesis, Vol. 2A, J. D. Morrison (Ed.), pp. 243. Academic Press, Orlando, FL.
  • [37] Xie J. H., Zhu S. F., Zhou Q. L., Chem. Rev. 111 (2011) 1731-1760.
  • [38] Denmark S. E., Beutner G. L., Angew. Chem. Int. Ed. 47 (2008)1560-1638.
  • [39] Suares A., Downey C. W., Fu G. C., J. Am. Chem. Soc. 127 (2005) 11244-11245.
  • [40] Paquin L., Hamelin J., Texier-Boullet F., Synthesis. (2006) 1635-1638.
  • [41] Abid M., Savolainen M., Landge S., Hu J., Suryaprakash G. K., Olah G. A., Torok, B., J. Flu. Chem. 128 (2007) 587-594.
  • [42] Barr D. A., Donegn G., Grigg R., J. Chem. Soc. Perkin Trans. 1 (1989) 1550-1551.
  • [43] Blackburn L., Taylor R. J. K., Org. Lett. 3 (2001) 1637-1639.
  • [44] Gopalakrishnan M., Sureshkumar P., Kanagarajan V., Thanusu J., Res. Chem. Intermed. 33 (2007) 541-548.
  • [45] Varma R. S., Green Chem. (1999) 43-45.
  • [46] Dutheuil G., Bonnaire S. C., Pannecoucke X., Angew. Chem. Int. Ed. Eng. 119 (2007) 1312-1314.
  • [47] Lipshutz, B. H., Shimizu, H., Angew. Chem. Int. Ed. 43 (2004) 2228-2230.
  • [48] Ali E., Jamal M. R. N., Efficient synthesis of imines by MCM-41-SO3H nanaocatalyst. No. A006, 14th international conference on synthetic organic chemistry, (ESCOC-14), 1-30, Nov. 2010.
  • [49] Hasaninejad A., Zare A., Sharghi H., Shekouhy,M., Arkicov. 11 (2008) 64-74.
  • [50] Zhang H., Syed S., Barbas, C. F., Org. Lett. 12 (2010) 708-711.
  • [51] Bode C. M., Ting A., Schaus S. E. A., Tetrahedron. 62 (2006) 11499-11505.
  • [52] Lidstrom P., Tierney J., Wathey B., Westman J., Tetrahedron. 57 (2001) 9225-9283.
  • [53] Vazquez M. A., Landa M., Reyes L., Tamariz M. J., Francisco, D., Synth. Commun. 34 (2004) 2705-2718.
  • [54] Hudlicky M., Oxidations in Organic Chemistry, ACS Monograph series, ACS, Washington 1990, DC.
  • [55] Landge S. M., Atanassova V., Thimmaiah M., Torok B., Tetrahedron Lett. 48 (2007) 5161-5164.
  • [56] France S., Shah M. H., Weatherwax A., Wack H., Roth J. P., Lectka T., J. Am. Chem. Soc. 127 (2004) 1206-1215
  • [57] Thirunarayanan G., Iup. J. Chem. 3(4) (2010) 35-54.
  • [58] Thirunarayanan G., Mayavel P., Thirumurthy K., Spectrochim. Acta. 75A (2012) 18-22.
  • [59] Thirunarayanan G., Ananthakrishna Nadar P. J. Korean Chem. Soc. 50 (2006) 183-190.
  • [60] Thirunarayanan G., Vanangamudi G., Sathiyendiran V., Ravi K., Indian J. Chem. 50B (2011) 593-604.
  • [61] Suresh R., Kamalakkannan D., Ranganathan K., Arulkumaran R., Sundararajan R., Sakthinathan S. P., Vijayakumar S., Sathiyamoorthy K. Mala V., Vanangamudi G., Thirumurthy K., Mayavel P., Thirunarayanan G., Spectrochim. Acta. 101A, (2013) 239-248.
  • [62] Swain C. G., Lupton Jr, E. C., J. Am. Chem. Soc. 90 (1968) 4328-4337.
  • [63] Mohan S. Saravanan J., Asian J. Chem. 14 (2002) 1331-1334.
  • [64] Janaki P., Sekar K. G., Thirunarayanan G., Organic Chemistry: An Indian J. 9(1) (2013) 68-80.
  • [65] Satyendra Deka, 2005. M. Pharm. Dissertation, PES College of Pharmacy, Banalore-560050.
  • [66] Janaki P., Sekar K. G., Thirunarayanan G., J. Saudi Chem. Soc. (2013) Doi.10.1016/j.jscs.2012.11.013
  • [67] Thirunarayanan G., Int. J. Chem. 1(4) (2012) 535-541.
  • [68] Arulkumaran R., Vijayakumar S., Sundararajan R., Sakthinathan S. P., Kamalakkannan D., Suresh R., Ranganathan K., Vanangamudi G., Thirunarayanan G., Int. Lett. Chem. Phys. Astro. 4 (2012) 17-38.
  • [69] Ranganathan K., Suresh R., Kamalakkannan D., Arulkumaran R., Sundararajan R., Sakthinathan S. P., Vijayakumar S., Vanangamudi G., Thirumurthy K., Mayavel P., Thirunarayanan G., Int. Lett. Chem. Phys. Astro. 4 (2012) 66-75.
  • [70] Arulkumaran R., Vijayakumar S., Sundararajan R., Sakthinathan S. P., Kamalakkannan D., Suresh R., Ranganathan Rajakumar P. R., Vanangamudi G., Thirunarayanan G., Int. Lett. Chem. Phys. Astro. 5 (2013) 21-38.
  • [71] Sakthinathan S. P., Suresh R., Mala V., Sathiyamoorthi K., Kamalakkannan D.,
  • Ranganathan, K., Arulkumaran, R., Vijayakumar, S., Sundararajan, R., Vanangamudi G., Thirunarayanan G., Int. Lett. Chem. Phys. Astro. 6 (2013) 77-90, 2013.
  • [72] Sathiyamoorthi K., Mala V., Suresh R., Sakthinathan S. P., Kamalakkannan D., Ranganathan K., Arulkumaran R., Sundararajan R., Vijayakumar S., Vanangamudi G., Thirunarayanan G., Int. Lett. Chem. Phys. Astro. 7(2) (2013) 102-119.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BPS2-0070-0007
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