A fast, simple and convenient procedure for the synthesis of fused pyrimidinone derivatives by using [Hmim][HSO4] as a green, efficient and reusable catalyst under solvent-free conditions
الموضوعات : Iranian Journal of CatalysisLeila Khazdooz 1 , Amin Zarei 2 , Abdol Hajipour 3 , Nafisehsadat Sheikhan 4
1 - Department of Science, Khorasgan Branch, Islamic Azad University, Isfahan 81595-158, Iran.
2 - Department of Science, Fasa Branch, Islamic Azad University, Post Box No 364, Fasa, 7461713591, Fars, Iran.
3 - Department of Pharmacology, University of Wisconsin, Medical School, 1300 University Avenue, Madison, 53706-1532, WI, USA.
Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, IR Iran.
4 - Department of Science, Najafabad Branch, Islamic Azad University, Isfahan, Iran.
الکلمات المفتاحية: Methylimidazolium hydrogen sulfate, Pyrimidinone, Bronsted acidic ionic liquid, Biginelli-type reaction,
ملخص المقالة :
In the present of methylimidazolium hydrogen sulfate, the synthesis of arylidene heterobicyclic pyrimidinones is studied by condensation of aromatic aldehyde, cyclopentanone, and urea or thiourea. Using solvent-free conditions, non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are the advantages of this method.
[1] C.O. Kappe, Acc. Chem. Res.33 (2000) 879–888.
[2] R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, T.A. Keating, Acc. Chem. Res. 29 (1996) 123–131.
[3] A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39 (2000) 3168–3210.
[4] C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. (2004) 4957–4980.
[5] D.J. Ramon, M. Yus. Angew. Chem. 44 (2005) 1602-1634.
[6] A. Ulaczyk-Lesanko, D.G. Hall, Curr. Opin. Chem. Biol. 9 (2005) 266-276.
[7] K.S. Atwal, G.C. Rovnyak, B.C. Ó Reilly, J. Schwartz, J. Org. Chem. 54 (1989) 5898–5907.
[8] C.O. Kappe, W.M.F. Fabian, M.A. Semones, Tetrahedron 53 (1997) 2803–2816.
[9] (a) M. Lei, L. Ma, L. Hu, Monatsh. Chem., 2010, 141, 1005-1008; (b) M. Rahman, A. Majee, A. Hajra, J. Heterocyclic Chem., 47 (2010) 1230-1233; (c) A. E. Rashad, A. H. Shamroukh, N.M. Yousif, M.A. Salama, H.S. Ali, M.M. Ali, A.E. Mahmoud, M. El-Shahat, Archiv der Pharmazie, 345 (2012) 729-738; (d) Q. Ren, X. Tan, H. He, Current Organic Synthesis, 8 (2011) 752-763; (e) A.R. Hajipour, Y. Ghayeb, N. Sheikhan, A.E. Ruoho, Synthetic Commun. 41 (2011) 2226-2233.(f) M.M. Heravi1, M. Saeedi1, Y.S. Beheshtiha1, H.A. Oskooie, Chem. Heterocyc. Compd. 47 (2011) 737-744.
[10] (a) H.I. El-Subbagh, S. M. Abu-Zaid, M.A. Mahran, F.A. Badria, A.M. Al-Obaid, J. Med. Chem. 43 (2000) 2915–2921; (b) T. Lorand, J. Deli, D. Szabo, A. Foeldesi, A. Zschunke, Pharmazie 40 (1985) 536-539.
[11] G.E.H. Elgemeie, A.M.E. Attia, S.S. Alkabai, Nucleos. Nucleot. Nucl. 19 (2000) 723-734.
[12] (a) A.E.G. Hammam, M.A. Sharaf, N.A.A. El-Hafez, Indian J. Chem., Sect. B 40 (2001) 213-221; (b) F. Al-Omran, N. Al-Awadi, J. Chem. Res. 10 (1995) 2201-2220; (c) M. A. Al-Omar, K.M. Youssef, M. A. El-Sherbeny, S.A.A. Awadalla, H.I. El-Subbagh, Arch. Pharm; (Weinheim Ger.) 338 (2005) 175-180; (d) M.I. Ali, A.E.G. Hammam, N.M. Youssef, J. Chem. Eng. Data 26 (1981) 214-215.
[13] Y. Zhu, S. Huang, Y. Pan, Eur. J. Org. Chem. (2005) 2354-2367.
[14] H. Zhang, Z. Zhou, Z. Yao, F. Xu, Q. Shen, Tetrahedron Lett. 50 (2009) 1622-1624.
[15] J.S. Wilkes, J. Mol. Catal. A: Chem. 214 (2004) 11-17.
[16] T. Welton, Chem. Rev. 99 (1999) 2071-2083.
[17] P. Wasserscheid, W. Keim, Angew. Chem., Int. Ed. 39 (2000) 3772-3789.
[18] T.L. Greaves, C.J. Drummond, Chem. Rev. 108 (2008) 206-237.
[19] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, Catal. Commun. 9 (2008) 89-96.
[20] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, J. Sulfur. Chem. 30 (2009) 46-52.
[21] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, Phosphorus Sulfur, and Silicon 184 (2009) 705-711.
[22] L. Khazdooz, A. Zarei, A.R. Hajipour, N. Sheikhan, Iranian J. Catal. 1 (2011) 1-9.
[23] D. Zhao, Y. Liao, Z. Zhang, Clean 35 (2007) 42-48.