
This work is licensed under a Creative Commons Attribution 4.0 International License.
Green Synthesis of Spiropyranone 3-Aryl-4-Methylcoumarin Derivatives using Carbonyldiimidazole
Corresponding Author(s) : D. Ashok
Asian Journal of Chemistry,
Vol. 32 No. 1 (2020): Vol 32 Issue 1
Abstract
A series of spiropyranone 3-aryl-4-methylcoumarin derivatives have been synthesized from monospiro-2-hydroxy acetophenone in a novel and efficient green method using imidazolyl intermediates and inorganic base. Imidazolyl intermediates were in turn generated by grinding the respective phenylacetic acid along with carbonyldiimidazole (CDI). Similarly, monospiro-2-hydroxy acetophenone derivatives were prepared selectively by avoiding formation of bis derivatives following literature procedure. The titled compounds were purified by preparative TLC technique and were characterized by IR, 1H NMR, 13C NMR as well as mass spectral methods.
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References
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F. Leonetti, A. Favia, A. Rao, R. Aliano, A. Paluszcak, R. W. Hartmann and A. Carotti, J. Med. Chem., 47, 6792 (2004); https://doi.org/10.1021/jm049535j.
L.M. Kabeya, A.A. de Marchi, A. Kanashiro, N.P. Lopes, C.H.T.P. de Silva, M.T. Pupo and Y.M. Lucisano-Valim, Bioorg. Med. Chem., 15, 1516 (2007); https://doi.org/10.1016/j.bmc.2006.10.068.
L. Piazzi, A. Cavalli, F. Colizzi, F. Belluti, M. Bartolini, F. Mancini, M. Recanatini, V. Andrisano and A. Rampa, Bioorg. Med. Chem. Lett., 18, 423 (2008); https://doi.org/10.1016/j.bmcl.2007.09.100.
K. Harada, H. Kubo, Y. Tomigahara, K. Nishioka, J. Takahashi, M. Momose, S. Inoue and A. Kojima, Bioorg. Med. Chem. Lett., 20, 272 (2010); https://doi.org/10.1016/j.bmcl.2009.10.111.
F. Borges, F. Roleira, N. Milhazes, L. Santana and E. Uriarte, Curr. Med. Chem., 12, 887 (2005); https://doi.org/10.2174/0929867053507315.
P. Anand, B. Singh and N. Singh, Bioorg. Med. Chem., 20, 1175 (2012); https://doi.org/10.1016/j.bmc.2011.12.042.
I.S. Vinyarov and M.G. Bogdanov, Eur. J. Med. Chem., 78, 198 (2014); https://doi.org/10.1016/j.ejmech.2014.03.053.
C. Mattsson, P. Svensson and C. Sonesson, Eur. J. Med. Chem., 73, 177 (2014); https://doi.org/10.1016/j.ejmech.2013.11.035.
F. Belluti, G. Fontana, L. dal Bo, N. Carenini, C. Giommarelli and F. Zunino, Bioorg. Med. Chem., 18, 3543 (2010); https://doi.org/10.1016/j.bmc.2010.03.069.
M.J. Matos, D. Viña, F.J. Borges, L. Santana and E. Uriarte, Bioorg. Med. Chem. Lett., 20, 5157 (2010); https://doi.org/10.1016/j.bmcl.2010.07.013.
D. Bogdal, J. Chem. Res. (S), 468 (1998); https://doi.org/10.1039/A801724G.
M. Trkovnik and Z. Ivezic, J. Heterocycl. Chem., 37, 137 (2009); https://doi.org/10.1002/jhet.5570370123.
S.H. Mashraqui, D. Vashi and H.D. Mistry, Synth. Commun., 34, 3129 (2004); https://doi.org/10.1081/SCC-200028575.
M.J. Matos, D. Viña, C. Picciau, F. Orallo, L. Santana and E. Uriarte, Bioorg. Med. Chem. Lett., 19, 3268 (2009); https://doi.org/10.1016/j.bmcl.2009.04.085.
M. M. Potdar, S.S. Mohile and M.M. Salunkhe, Tetrahedron Lett., 42, 9285 (2001); https://doi.org/10.1016/S0040-4039(01)02041-X.
Y. Ming and D.W. Boykin, Heterocycles, 26, 3229 (1987); https://doi.org/10.3987/R-1987-12-3229.
L. Santana, H. González-Díaz, E. Quezada, E. Uriarte, M. Yáñez, D. Viña and F.J. Orallo, Med. Chem., 51, 6740 (2008); https://doi.org/10.1021/jm800656v.
R.S. Mali and S.G. Tilve, Synth. Commun., 20, 1781 (1990); https://doi.org/10.1080/00397919008053103.
R.S. Mali and P.P. Joshi, Synth. Commun., 31, 2753 (2001); https://doi.org/10.1081/SCC-100105321.
A.K. Prasad, H.N. Pati, A. Azim, S. Trikha and Poonam, Bioorg. Med. Chem., 7, 1973 (1999); https://doi.org/10.1016/S0968-0896(99)00109-1.
H.M.F. Madkour, Heterocycles, 36, 947 (1993); https://doi.org/10.3987/COM-92-6079.
N. Hans, M. Singhi, V. Sharma and S.K. Grover, Indian J. Chem., 35B, 1159 (1996).
D.V. Kadnikov and R.C. Larock, J. Organomet. Chem., 687, 425 (2003); https://doi.org/10.1016/S0022-328X(03)00786-1.
P. Bäuerle and M.S. Schiedel, Process for the Parallel Synthesis of Atleast Two Organic Dyes and Substituted Coumarin Derivatives and Arylboronic Acid Propanediol Esters, WO Patent 2001068635A2 (2001).
D. Olmedo, R. Sancho, L.M. Bedoya, J.L. López-Pérez, E.D. Olmo, E. Muñoz, J. Alcamí, M.P. Gupta and A.S. Feliciano, Molecules, 17, 9245 (2012); https://doi.org/10.3390/molecules17089245.
M. Roberct, E. Angrooan and D.G. Gerhared, Can. J. Chem., 66, 1701 (1988); https://doi.org/10.1139/v88-275.
S. Rahmani-Nezhad, L. Khosravani, M. Saeedi, L. Firoozpour, K. Divsalar, Y. Pourshojaei, Y. Sarrafi, H. Nadri, A. Moradi, M. Mahdavi, A, Shafiee and A. Foroumadi, Synth. Commun., 45, 741 (2015); https://doi.org/10.1080/00397911.2014.979947.
M. Roussaki, C.A. Kontogiorgis, D. Hadjipavlou-Litina, S. Hamilakis and A. Detsi, Bioorg. Med. Chem. Lett., 20, 3889 (2010); https://doi.org/10.1016/j.bmcl.2010.05.022.
S.K. Verma, R. Ghorpade, A. Pratap and M.P. Kaushik, Tetrahedron Lett., 53, 2373 (2012); https://doi.org/10.1016/j.tetlet.2012.01.125.