Ionic liquids as efficient catalysts for synthesis of phosphorylated dialkyl succinates containing phthalazin-1-one moieties
الموضوعات : Iranian Journal of CatalysisZiba Tavakoli 1 , Elnaz Ghasemi 2 , Issa Yavari 3
1 - Department of Chemistry, Islamic Azad University, Science and Research Branch, Ponak Tehran, Iran.
2 - Department of Chemistry, Islamic Azad University, Science and Research Branch, Ponak Tehran, Iran.
3 - Department of Chemistry, Islamic Azad University, Science and Research Branch, Ponak Tehran, Iran.
الکلمات المفتاحية: Ionic Liquid, Phosphorylation, Organocatalysis, 2H-Phthalazin-1-one, Acetylenic ester,
ملخص المقالة :
Ionic liquids such as 1,3-dialkylimidazolium salts make excellent catalysts and solvents for synthesis of dialkyl 2-(dialkoxyphosphoryl)-3-(1-oxo-1-H-phthalazin-2-yl)succinates from 2H-phthalazin-1-one, dialkyl acetylenedicarboxylates, and trialkyl phosphites. Under similar conditions, triphenyl phosphite led to dialkyl 2-(diphenoxyphosphoryl)-3-(1-oxo-1-H-phthalazin-2-yl)succinates. The ionic liquid was readily recycled and can be reused four times without significant loss of activity or mass.
[1] T. Welton, Chem. Rev., 99 (1999) 2071-2094.
[2] R.D. Rogers, K. R. Seddon (eds) In Ionic Liquids: Industrial Applications to Green Chemistry, ACS Symposium Series 818, ACS, Washington, DC, 2002.
[3] Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, Germany, 2003.
[4] I. Yavari, E. Kowsari, Tetrahedron Lett., 48 (2007) 3753–3756.
[5] H.R. Hudson, in The Chemistry of Organophosphorus Compounds, Volume 1. Primary, Secondary and Tertiary Phosphines, Polyphosphines and Heterocyclic Organophosphorus (III) Compounds, ed. by F.R. Hantley; Wiley: New York, 1990, pp. 386-472.
[6] R. Engel, Synthesis of Carbon-Phosphorus Bonds; CRC Press: Boca Raton, FL, 1988.
[7] R.A. Cherkasov, M. A. Pudovik, Russ. Chem. Rev., 63 (1994) 1019-1023.
[8] K.M. Pietrusiewiz, M. Zablocka, Chem. Rev., 94 (1994) 1375-1394.
[9] R. Burgada, Y. Leroux, Y.U. El Khoshnieh, Tetrahedron Lett., 22 (1981) 3533-3536.
[10] I. Yavari, R. Hajinasiri, S. Z. Sayyed-Alangi, N. Iravani, Monatsh. Chem. 139 (2008) 1029-1032.
[11] E. Breitmaier and W. Voelter, Carbon-13 NMR Spectroscopy, 3rd. ed., VCH; New York: 1990, pp 250-254.
[12] R.S. Edmundson, Phosphorus Acid Derivatives. In Comprehensive Organic Chemistry, ed. by D.H.R. Barton, W. D. Ollis, Pergamon Press; Oxford 1979, Vol. 2, Ch. 10.3.
[13] R. Hajipour, F. Rafiee, Iran. J. Catal. 2 (2012) 23-26.