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Condensation of Lactones with Primary Diamines
Corresponding Author(s) : Abdellatif El Kihel
Asian Journal of Chemistry,
Vol. 33 No. 2 (2021): Vol 33 Issue 2
Abstract
The condensation of dehydroacetic acid and 4-hydroxy-6-methylpyran-2-one with primary diamine derivatives such as hydrazine, 1,2-diaminoethane and 1,6-diaminohexane yielded bispyrone and bispyridone derivatives has been reported. The condensation of 4-hydroxy-6-methylpyran-2-one with hydrazine in acetonitrile generated another bispyrazole product but in n-butanol, this reaction afforded the bispyridones. The structures of the synthesized bispyrazoles were examined by spectroscopy and X-ray diffraction analysis, while those of bispyridones were established by spectroscopy data (NMR, mass). Some new complexes were also synthesized in order to show the behaviour of ligands with suitable crystals for X-ray analysis.
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- E. Sahan, I. Yildirim and S. Albayrak, Heterocycl. Commun., 19, 183 (2013);https://doi.org/10.1515/hc-2012-0167
- P. Gupta, J.K. Gupta and A.K. Halve, Int. J. Pharm. Sci. Res., 6, 2291 (2015).
- R.R. Parajuli, P.P. Pokhrel, A.K. Tiwari and J. Banerjee, J. Appl. Pharm. Res., 1, 5 (2013).
- E.A. Ahmed, J. Mex. Chem. Soc., 59, 181 (2015).
- R. Mukherjee, Coord. Chem. Rev., 203, 151 (2000);https://doi.org/10.1016/S0010-8545(99)00144-7
- A. Otero, J. Fernández-Baeza, A. Antiñolo, J. Tejeda and A. Lara-Sánchez, Dalton Trans., 1499 (2004);https://doi.org/10.1039/B401425A
- K. Chkirate, N.K. Sebbar, K. Karrouchi and E.M. Essassi, J. Mar. Chim. Heterocycl., 17, 1 (2018).
- L. Hennig, R. Kirmse, O. Hammerich, S. Larsen, H. Frydendahl, H. Toftlund and J. Becher, Inorg. Chim. Acta, 234, 67 (1995);https://doi.org/10.1016/0020-1693(95)04479-S
- J.C. Rasmussen, I. Toftlund, A.N. Nivorzhkin, J. Bourassa and P.C. Ford, Inorg. Chim. Acta, 251, 291 (1996);https://doi.org/10.1016/S0020-1693(96)05282-6
- S. Pal, A.K. Barik, S. Gupta, S. Roy, T.N. Mandal, A. Hazra, M.S. El Fallah, R.J. Butcher, S.-M. Peng, G.-H. Lee and S.K. Kar, Polyhedron, 27, 357 (2008);https://doi.org/10.1016/j.poly.2007.09.037
- L.D. Popov, S.I. Levchenkov, I.N. Shcherbakov, V.V. Lukov, K.Y. Suponitsky and V.A. Kogan, Inorg. Chem. Commun., 17, 1 (2012);https://doi.org/10.1016/j.inoche.2011.11.020
- M.R. Malachowski, J. Carden, M.G. Davidson, W.L. Driessen and J. Reedijk, Inorg. Chim. Acta, 257, 59 (1997);https://doi.org/10.1016/S0020-1693(96)05448-5
- P. Gamez, J.V. von Harras, O. Roubeau, W.L. Driessen and J. Reedijk, Inorg. Chim. Acta, 324, 27 (2001);https://doi.org/10.1016/S0020-1693(01)00498-4
- H.S. Abbo and S.J.J. Titinchi, Molecules, 18, 4728 (2013);https://doi.org/10.3390/molecules18044728
- N.V. Fischer, G. Türkoglu and N. Burzlaff, Curr. Bioact. Compd., 5, 277 (2009);https://doi.org/10.2174/157340709789816438
- M. Pellei, V. Gandin, L. Marchió, C. Marzano, L. Bagnarelli and C. Santini, Molecules, 24, 1761 (2019);https://doi.org/10.3390/molecules24091761
- M.B. Morelli, C. Amantini, G. Santoni, M. Pellei, C. Santini, C. Cimarelli, E. Marcantoni, M. Petrini, F. del Bello, G. Giorgioni, A. Piergentili and W. Quaglia, New J. Chem., 42, 11878 (2018);https://doi.org/10.1039/C8NJ01763H
- M. Pellei, G. Papini, A. Trasatti, M. Giorgetti, D. Tonelli, M. Minicucci, C. Marzano, V. Gandin, G. Aquilanti, A. Dolmella and C. Santini, Dalton Trans., 40, 9877 (2011);https://doi.org/10.1039/c1dt10486a
- N.H. Metwally, F.M. Abdelrazek and M.T. Jaafar, J. Heterocycl. Chem., 52, 358 (2015);https://doi.org/10.1002/jhet.2043
- M.T. Cocco, C. Congiu and V. Onnis, Eur. J. Med. Chem., 35, 545 (2000);https://doi.org/10.1016/S0223-5234(00)00149-5
- T.B. Hadda, H. Stoeckli-Evans, A. Kerbal, A.E. Fatmi, M.F. Baba, N.B. Larbi, M. Daoudi and R.N. Patel, ARKIVOC, 15, 215 (2007);https://doi.org/10.3998/ark.5550190.0008.f21
- Z. Bouanane, M. Bounekhel, M. Ellkoli, A. Takfaoui, F. Abrigach, R. Boyaala and R. Touzani, J. Pure Appl. Sci., 1, 62 (2015).
- J. Reedijk and E. Bouwman, Bioinorganic Catalysis, Marcel Dekker: New York (1999).
- K.D. Karlin and Z. Tyeklar, Bioinorganic Chemistry of Copper, Chapman and Hall: New York (1993).
- E.A. Abouelhaoul, S. Hamid, A. El-Kihel, M. Saadi and L. El-Ammari, IUCrData, 4, x191348 (2019);https://doi.org/10.1107/S2414314619013488
- M. El Abbassi, B. Djerrari, E.M. Essassi and J. Fifani, Tetrahedron Lett., 30, 7069 (1989);https://doi.org/10.1016/S0040-4039(01)93425-2
- G. Venkatachalam and R. Ramesh, Inorg. Chem. Commun., 8, 1009 (2005);https://doi.org/10.1016/j.inoche.2005.08.004
- S. Castillo, H. Ouaddahi and V. Hérault, Bull. Soc. Chim. Fr., 11, 257 (1982).
- C.S. Wang, J.P. Easterly and N.E. Skelly, Tetrahedron, 27, 2581 (1971);https://doi.org/10.1016/S0040-4020(01)98046-9
- B. Djerrari, E.M. Essassi and J. Fifani, Bull. Soc. Chim. Belg., 102, 565 (1993);https://doi.org/10.1002/bscb.19931020902
- A. El-Kihel, M. Benchidmi, E.M. Essassi, P. Bauchat and R. Danion-bougot, Synth. Commun., 29, 2435 (1999);https://doi.org/10.1080/00397919908086250
- B. Djerrari, E.M. Essassi, J. Fifani and B. Garrigues, C.R. Chim., 5, 177 (2002);https://doi.org/10.1016/S1631-0748(02)01363-2
- M. El Abbassi, E.M. Essassi and J. Fifani, Bull. Soc. Chim. Belg., 106, 205 (1997).
- M. Fettouhi, A. Boukhari, B. El Otmani and E.M. Essassi, Acta Crystallogr., C52, 1031 (1996);https://doi.org/10.1107/S0108270195013680
- G.M. Sheldrick, Acta Crystallogr., A71, 3 (2015);https://doi.org/10.1107/S2053273314026370
- G.M. Sheldrick, Acta Crystallogr., C71, 3 (2015);https://doi.org/10.1107/S2053229614024218
References
E. Sahan, I. Yildirim and S. Albayrak, Heterocycl. Commun., 19, 183 (2013);https://doi.org/10.1515/hc-2012-0167
P. Gupta, J.K. Gupta and A.K. Halve, Int. J. Pharm. Sci. Res., 6, 2291 (2015).
R.R. Parajuli, P.P. Pokhrel, A.K. Tiwari and J. Banerjee, J. Appl. Pharm. Res., 1, 5 (2013).
E.A. Ahmed, J. Mex. Chem. Soc., 59, 181 (2015).
R. Mukherjee, Coord. Chem. Rev., 203, 151 (2000);https://doi.org/10.1016/S0010-8545(99)00144-7
A. Otero, J. Fernández-Baeza, A. Antiñolo, J. Tejeda and A. Lara-Sánchez, Dalton Trans., 1499 (2004);https://doi.org/10.1039/B401425A
K. Chkirate, N.K. Sebbar, K. Karrouchi and E.M. Essassi, J. Mar. Chim. Heterocycl., 17, 1 (2018).
L. Hennig, R. Kirmse, O. Hammerich, S. Larsen, H. Frydendahl, H. Toftlund and J. Becher, Inorg. Chim. Acta, 234, 67 (1995);https://doi.org/10.1016/0020-1693(95)04479-S
J.C. Rasmussen, I. Toftlund, A.N. Nivorzhkin, J. Bourassa and P.C. Ford, Inorg. Chim. Acta, 251, 291 (1996);https://doi.org/10.1016/S0020-1693(96)05282-6
S. Pal, A.K. Barik, S. Gupta, S. Roy, T.N. Mandal, A. Hazra, M.S. El Fallah, R.J. Butcher, S.-M. Peng, G.-H. Lee and S.K. Kar, Polyhedron, 27, 357 (2008);https://doi.org/10.1016/j.poly.2007.09.037
L.D. Popov, S.I. Levchenkov, I.N. Shcherbakov, V.V. Lukov, K.Y. Suponitsky and V.A. Kogan, Inorg. Chem. Commun., 17, 1 (2012);https://doi.org/10.1016/j.inoche.2011.11.020
M.R. Malachowski, J. Carden, M.G. Davidson, W.L. Driessen and J. Reedijk, Inorg. Chim. Acta, 257, 59 (1997);https://doi.org/10.1016/S0020-1693(96)05448-5
P. Gamez, J.V. von Harras, O. Roubeau, W.L. Driessen and J. Reedijk, Inorg. Chim. Acta, 324, 27 (2001);https://doi.org/10.1016/S0020-1693(01)00498-4
H.S. Abbo and S.J.J. Titinchi, Molecules, 18, 4728 (2013);https://doi.org/10.3390/molecules18044728
N.V. Fischer, G. Türkoglu and N. Burzlaff, Curr. Bioact. Compd., 5, 277 (2009);https://doi.org/10.2174/157340709789816438
M. Pellei, V. Gandin, L. Marchió, C. Marzano, L. Bagnarelli and C. Santini, Molecules, 24, 1761 (2019);https://doi.org/10.3390/molecules24091761
M.B. Morelli, C. Amantini, G. Santoni, M. Pellei, C. Santini, C. Cimarelli, E. Marcantoni, M. Petrini, F. del Bello, G. Giorgioni, A. Piergentili and W. Quaglia, New J. Chem., 42, 11878 (2018);https://doi.org/10.1039/C8NJ01763H
M. Pellei, G. Papini, A. Trasatti, M. Giorgetti, D. Tonelli, M. Minicucci, C. Marzano, V. Gandin, G. Aquilanti, A. Dolmella and C. Santini, Dalton Trans., 40, 9877 (2011);https://doi.org/10.1039/c1dt10486a
N.H. Metwally, F.M. Abdelrazek and M.T. Jaafar, J. Heterocycl. Chem., 52, 358 (2015);https://doi.org/10.1002/jhet.2043
M.T. Cocco, C. Congiu and V. Onnis, Eur. J. Med. Chem., 35, 545 (2000);https://doi.org/10.1016/S0223-5234(00)00149-5
T.B. Hadda, H. Stoeckli-Evans, A. Kerbal, A.E. Fatmi, M.F. Baba, N.B. Larbi, M. Daoudi and R.N. Patel, ARKIVOC, 15, 215 (2007);https://doi.org/10.3998/ark.5550190.0008.f21
Z. Bouanane, M. Bounekhel, M. Ellkoli, A. Takfaoui, F. Abrigach, R. Boyaala and R. Touzani, J. Pure Appl. Sci., 1, 62 (2015).
J. Reedijk and E. Bouwman, Bioinorganic Catalysis, Marcel Dekker: New York (1999).
K.D. Karlin and Z. Tyeklar, Bioinorganic Chemistry of Copper, Chapman and Hall: New York (1993).
E.A. Abouelhaoul, S. Hamid, A. El-Kihel, M. Saadi and L. El-Ammari, IUCrData, 4, x191348 (2019);https://doi.org/10.1107/S2414314619013488
M. El Abbassi, B. Djerrari, E.M. Essassi and J. Fifani, Tetrahedron Lett., 30, 7069 (1989);https://doi.org/10.1016/S0040-4039(01)93425-2
G. Venkatachalam and R. Ramesh, Inorg. Chem. Commun., 8, 1009 (2005);https://doi.org/10.1016/j.inoche.2005.08.004
S. Castillo, H. Ouaddahi and V. Hérault, Bull. Soc. Chim. Fr., 11, 257 (1982).
C.S. Wang, J.P. Easterly and N.E. Skelly, Tetrahedron, 27, 2581 (1971);https://doi.org/10.1016/S0040-4020(01)98046-9
B. Djerrari, E.M. Essassi and J. Fifani, Bull. Soc. Chim. Belg., 102, 565 (1993);https://doi.org/10.1002/bscb.19931020902
A. El-Kihel, M. Benchidmi, E.M. Essassi, P. Bauchat and R. Danion-bougot, Synth. Commun., 29, 2435 (1999);https://doi.org/10.1080/00397919908086250
B. Djerrari, E.M. Essassi, J. Fifani and B. Garrigues, C.R. Chim., 5, 177 (2002);https://doi.org/10.1016/S1631-0748(02)01363-2
M. El Abbassi, E.M. Essassi and J. Fifani, Bull. Soc. Chim. Belg., 106, 205 (1997).
M. Fettouhi, A. Boukhari, B. El Otmani and E.M. Essassi, Acta Crystallogr., C52, 1031 (1996);https://doi.org/10.1107/S0108270195013680
G.M. Sheldrick, Acta Crystallogr., A71, 3 (2015);https://doi.org/10.1107/S2053273314026370
G.M. Sheldrick, Acta Crystallogr., C71, 3 (2015);https://doi.org/10.1107/S2053229614024218