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One-Pot Synthesis of 5-Allyl-8-hydroxy-7-methoxy-2-methylquinoline
Corresponding Author(s) : I.M. Sudarma
Asian Journal of Chemistry,
Vol. 28 No. 8 (2016): Vol 28 Issue 8
Abstract
The main aim of this research was to develop novel Schiff base compounds from readily accessed natural products, in particular eugenol (1). A new 5-allyl-8-hydroxy-7-methoxy-2-methylquinoline was synthesized via one-pot Schiff base reaction of nitro-eugenol with acetaldehyde. Normally Schiff base was prepared directly from primary amine and aldehyde, but in this paper it was prepared directly from nitro compound such as nitro-eugenol and acetaldehyde with three different catalyst namely: Fe/HCl or Zn/formic acid or Sn/HCl in ethanol. These catalysts were used to optimize the yield of Schiff base without isolating the primary amine. Nitro eugenol (2) was synthesized in good yield by adding potassium hydrogen sulfate and ammonium nitrate. This nitro-eugenol was treated with Fe/HCl or Zn/formic acid or Sn/HCl in ethanol under refluxed condition to afford 5-allyl-8-hydroxy-7-methoxy-2-methylquinoline (3) (73.49 %), (43.50 %) and (40.14 %) respectively.
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- I M. Sudarma, M. Ulfa and Sarkono, Indo. J. Chem., 9, 267 (2007).
- I.M. Sudarma, N. Wazni, N. Wildawaty, E. Yuanita and I.W. Suana, Asian J. Chem., 26, 173 (2014); doi:10.14233/ajchem.2014.19039.
- I.M. Sudarma, A. Kusnandini and M.G. Darmayanti, J. Nat. Prod., 8, 27 (2015).
- I.M. Sudarma, S. Hizmi and M.G. Darmayanti, Asian J. Chem., 27, 3887 (2015); doi:10.14233/ajchem.2015.19046.
- S.M. Devidas, S.H. Quadri, S.A. Kamble, F.M. Syed and D.Y. Vyavhare, J. Chem. Pharm. Res., 3, 489 (2011).
- H. Naeimi, F. Salimi and K. Rabiei, J. Mol. Catal. A: Chem., 260, 10 (2006); doi:10.1016/j.molcata.2006.06.055.
- G.A. Shallangwa, H. Musa and E. Ogbe, J. Progr. Res. Chem., 1, 14 (2015).
- K. Brodowska and E.L. Chruscinska, Chemik, 68, 129 (2014).
- A. Adabiardakani, M. Hakimi and H. Kargar, World Appl. Program., 2, 472 (2012).
- B. Mistry and S. Jauhari, Arch. Appl. Sci. Res., 2, 332 (2010).
- B. Baghernejad, M.M. Heravi, H.A. Oskooie and Y.Sh. Beheshtiha, G.U. J. Sci. (Iran), 22, 169 (2009).
- P.V. Rao, A.V.G.S. Prasad and P.S.S. Prasad, Int. J. Pharm., 4, 215 (2014).
- A.B. Gamble, J. Garner, C.P. Gordon, S.M.J. O’Conner and P.A. Keller, Synth. Commun., 37, 2777 (2007); doi:10.1080/00397910701481195.
References
I M. Sudarma, M. Ulfa and Sarkono, Indo. J. Chem., 9, 267 (2007).
I.M. Sudarma, N. Wazni, N. Wildawaty, E. Yuanita and I.W. Suana, Asian J. Chem., 26, 173 (2014); doi:10.14233/ajchem.2014.19039.
I.M. Sudarma, A. Kusnandini and M.G. Darmayanti, J. Nat. Prod., 8, 27 (2015).
I.M. Sudarma, S. Hizmi and M.G. Darmayanti, Asian J. Chem., 27, 3887 (2015); doi:10.14233/ajchem.2015.19046.
S.M. Devidas, S.H. Quadri, S.A. Kamble, F.M. Syed and D.Y. Vyavhare, J. Chem. Pharm. Res., 3, 489 (2011).
H. Naeimi, F. Salimi and K. Rabiei, J. Mol. Catal. A: Chem., 260, 10 (2006); doi:10.1016/j.molcata.2006.06.055.
G.A. Shallangwa, H. Musa and E. Ogbe, J. Progr. Res. Chem., 1, 14 (2015).
K. Brodowska and E.L. Chruscinska, Chemik, 68, 129 (2014).
A. Adabiardakani, M. Hakimi and H. Kargar, World Appl. Program., 2, 472 (2012).
B. Mistry and S. Jauhari, Arch. Appl. Sci. Res., 2, 332 (2010).
B. Baghernejad, M.M. Heravi, H.A. Oskooie and Y.Sh. Beheshtiha, G.U. J. Sci. (Iran), 22, 169 (2009).
P.V. Rao, A.V.G.S. Prasad and P.S.S. Prasad, Int. J. Pharm., 4, 215 (2014).
A.B. Gamble, J. Garner, C.P. Gordon, S.M.J. O’Conner and P.A. Keller, Synth. Commun., 37, 2777 (2007); doi:10.1080/00397910701481195.