We have disclosed the synthesis of pyranoquinoline derivatives via a one-pot reaction of 4-nitro benz aldehyde, malononitrile/ethyl cyanoacetate and 8-hydroxyquinoline using 30 mol.% DMAP in ethanol under reflux conditions. The Fourier transform infrared spectra of ethyl 2-amino-4-(4-nitrophenyl)-4H-pyra no[3,2-h]quinoline-3-carboxylate were recorded within the range 4000–400 cm–1. The Hartree–Fock and density functional theory on the 6-311G basis set have been utilized to calculate molecular geometry, vibrational frequencies, atomic charges and thermodynamic parameters. Further, the vibrational energy distribution analysis program was applied to assign the vibrational wavenumbers based on potential energy distribution. The HOMO–LUMO energies, the temperature dependence of the thermodynamic properties, the total electron density, and molecular electrostatic potential maps are also studied.
Similar content being viewed by others
References
S. M. Wickel, C. A. Citron, and J. S. Dickschat, Eur. J. Org. Chem., 2906–2913 (2013).
J. A. Makawana, M. P. Patel, and R. G. Patel, Arch. Pharm., 345, 314–322 (2012).
Y. Deng, J. P. Lee, M. Tianasoa-Ramamonjy, J. K. Synder, S. A. D. Etages, D. Synder, M. P. Kanada, and C. J. Turner, J. Nat. Prod., 63, 1082–1089 (2000).
N. A. Keiko, L. G. Stepanova, M. G. Voronkov, G. I. Potapova, N. O. Gudratov, and E. M. Treshchalina, J. Pharm. Chem., 36, 407–409 (2002).
S. Prado, H. Ledeit, S. Michel, M. Koch, J. C. Darbord, S. T. Cole, F. Tillequin, and P. Brodin, Bioorg. Med. Chem., 14, 5423–5428 (2006).
A. R. Saundane, K. Vijaykumar, and A. V. Vaijinath, Bioorg. Med. Chem. Lett., 23, 1978–1984 (2013).
P. G. Pietta, J. Nat. Prod., 63, 1035–1042 (2000).
M. D. Aytemir and B. Özçelik, Eur. J. Med. Chem., 45, 4089–4095 (2010).
P. W. Smith, S. L. Sollis, P. D. Howes, P. C. Cherry, I. D. Starkey, K. N. Cobley, H. Weston, J. Scicinski, A. Merritt, A. Whittington, P. Wyatt, N. Taylor, D. Green, R. Bethell, S. Madar, R. J. Fenton, P. J. Morley, T. Pateman, and A. Beresford, J. Med. Chem., 41, 787–797 (1998).
A. Venkatesham, R. S. Rao, K. Nagaiah, J. S. Yadav, G. RoopaJones, S. J. Basha, B. Sridhar, and A. Addlagatta, Med. Chem. Commun., 3, 652–658 (2012).
L. Bonsignore, G. Loy, D. Secci, and A. Calignano, Eur. J. Med. Chem., 28, 517–520 (1993).
D. Armetso, W. M. Horspool, N. Martin, A. Ramos, and C. Seoane, J. Org. Chem., 54, 3069–3072 (1989).
K. H. Lee, S. M. Kim, J. Y. Kim, Y. K. Kim, and S. S. Yoon, Bull. Korean Chem. Soc., 31, 2884–2888 (2010).
R. Klingenstein, P. Melnyk, S. R. Leliveld, A. Ryckebusch, and C. Korth, J. Med. Chem., 49, 5300–5308 (2006).
S. Vandekerckhove, H. G. Tran, T. Desmet, and M. D'hooghe, Bioorg. Med. Chem. Lett., 23, 4641–4643 (2013).
K. C. Fang, Y. L. Chen, J. Y. Sheu, T. C. Wang, and C. C. Tzeng, J. Med. Chem., 43, 3809–3812 (2000).
A. K. Sadana, Y. Mirza, K. R. Aneja, and O. Prakash, Eur. J. Med. Chem., 38, 533–536 (2003).
Y. L. Chen, I. L. Chen, C. M. Lu, C. C. Tzeng, L. T. Tsao, and J. P. Wang, Bioorg. Med. Chem., 12, 387–392 (2004).
G. Barbosa-Lima, A. M. Moraes, A. S. Araújo, E. T. Silva, C. S. Freitas, Y. R. Vieira, A. Marttorelli, J. C. Neto,
P. T. Bozza, M. V. N. Souza, and T. M. L. Souza, Eur. J. Med. Chem., 127, 334–340 (2017).
K. Rurack, A. Danel, K. Rotkiewicz, D. Grabka, M. Spieles, and W. Rettig, Org. Lett.,4, 4647–4650 (2002).
F. Liang, Z. Xie, L. Wang, X. Jing, and F. Wang, Tetrahedron Lett., 43, 3427–3430 (2002).
N. J. Parmar, R. A. Patel, B. D. Parmar, and N. P. Talpada, Bioorg. Med. Chem. Lett., 23, 1656 (2013).
P. Gunasekaran, P. Prasanna, and S. Perumal, Tetrahedron Lett., 55, 329 (2014).
Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford, CT (2013).
M. H. Jamroz, Vibrational Energy Distribution Analysis VEDA 4, Warsaw (2004).
A. D. Becke, J. Chem. Phys., 98, 5648 (1993).
A. D. Becke, Phys. Rev. A, 38, 3098 (1988).
C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, 785 (1988).
A. Frisch, A. B. Neilson, and A. J. Holder, GAUSSVIEW User Manual, Gaussian Inc. Pittsburgh, PA (2000).
R. S. Mulliken, J. Chem. Phys., 23, 1833 (1955).
H. Tanak, Y. Köysal, Y. Ünver, M. Yavuz, S. Isık, and K. Sancak, Mol. Phys., 108, 127 (2010).
S. Muthu and E. I. Paulraj, Solid State Sci., 14, 476 (2012).
R. Mathammal, N. Jayamani, and N. Geetha, J. Spectrosc., 2013, 171735 (2013).
E. Kavitha, N. Sundaraganesan, and S. Sebastian, Ind. J. Pure Appl. Phys., 48, 20–30 (2010)
A. Jayaprakash, V. Arjunan, and S. Mohan, Spectrochim. Acta, A, 81, 620–630 (2011).
J. BevanOtt and J. Boerio-Goates, Chemical Thermodynamics: Principles and Applications, Academic Press, San Diego (2000).
I. Fleming, Frontier Orbitals and Organic Chemical Reactions, John Wiley and Sons, New York (1976).
J. M. Semanario, Recent Developments and Applications of Modern Density Functional Theory, 4, Elsevier, The Netherlands (1996).
T. Yesilkaynak, G. Binzer, F. Mehmet Emen, U. Florke, N. Kulcu, and H. Arslan, Eur. J. Chem., 1, 1 (2010).
B. Kosar and C. Albayrak, Spectrochim. Acta, A, 78, 96 (2011).
Author information
Authors and Affiliations
Corresponding author
Additional information
Abstract of article is published in Zhurnal Prikladnoi Spektroskopii, Vol. 86, No. 4, p. 666, July–August, 2019.
Rights and permissions
About this article
Cite this article
Kour, P., Kumar, A., Uppal, A. et al. Synthesis and Computational Studies of Molecular Structure and Vibrational Spectra of 2-Amino-4-(4-Nitrophenyl)-4H-Pyrano-[3,2-H]Quinolines. J Appl Spectrosc 86, 715–725 (2019). https://doi.org/10.1007/s10812-019-00885-3
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10812-019-00885-3