Citation: Ravibabu Velpula, Janardhan Banothu, Rajitha Gali, Rajitha Deshineni, Rajitha Bavantula. 1-Sulfopyridinium chloride: Green and expeditious ionic liquid for the one-pot synthesis of fused 3,4-dihydropyrimidin-2(1H)-ones and thiones under solvent-free conditions[J]. Chinese Chemical Letters, ;2015, 26(3): 309-312. doi: 10.1016/j.cclet.2014.11.030 shu

1-Sulfopyridinium chloride: Green and expeditious ionic liquid for the one-pot synthesis of fused 3,4-dihydropyrimidin-2(1H)-ones and thiones under solvent-free conditions

1.
a Department of Chemistry, National Institute of Technology, Warangal 506 004, India;
2.
b Department of Chemistry, Osmania University, Hyderabad 500 007, India

Corresponding author: Rajitha Bavantula,
Received Date: 21 July 2014
Available Online: 27 October 2014

1-Sulfopyridinium chloride portrayed as an efficient and recyclable ionic liquid for the synthesis of fused 3,4-dihydropyrimidin-2(1H)-ones and thiones via a modified Biginelli reaction involving one-pot three component condensation of 6-methoxy-1-tetralone, arylaldehydes and urea/thiourea under solventfree conditions. Analytically pure products are formed within 10-20 min in excellent yields.
- Fused 3,4-dihydropyrimidin-2(1H)-ones,
- One-pot three component reaction,
- Solvent-free condition,
- 1-Sulfopyridinium chloride,
- Thiones
1. [1]
  [1] W. Zhang, B.W. Cue, Green Techniques for Organic Synthesis and Medicinal Chemistry, Wiley, Chichester, 2012.
2. [2]
  [2] A.M. Inamuddin, Green Solvents II: Properties and Applications in Chemistry, Springer, London, 2012.
3. [3]
  [3] A. Agarwal, K. Srivastava, S.K. Puri, P.M.S. Chauhan, Antimalarial activity and synthesis of new trisubstituted pyrimidines, Bioorg. Med. Chem. Lett. 15 (2005) 3130-3132.
4. [4]
  [4] H.T. Rajesh, H.R. Atish, D.H. Girish, et al., The novel 3,4-dihydropyrimidin-2(1H)-one urea derivatives of N-aryl urea: synthesis, anti-inflammatory, antibacterial and antifungal activity evaluation, Bioorg. Med. Chem. Lett. 21 (2011) 4648-4651.
5. [5]
  [5] S.W. Fewell, C.M. Smith, M.A. Lyon, et al., Small molecule modulators of endogenous and co-chaperone-stimulated Hsp70 ATPase activity, Biol. Chem. 279 (2004) 51131-51140.
6. [6]
  [6] C.O. Kappe, Biologically active dihydropyrimidones of the Biginelli-type -a literature survey, Eur. J. Med. Chem. 35 (2000) 1043-1052.
7. [7]
  [7] K.S. Atwal, B.N. Swanson, S.E. Unger, et al., Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents, J. Med. Chem. 34 (1991) 806-811.
8. [8]
  [8] A.D. Patil, N.V. Kumar, W.C. Kokke, et al., Novel alkaloids from the sponge Batzella: inhibitors of HIV gp120-human CD4 binding, J. Org. Chem. 60 (1995) 1182-1188.
9. [9]
  [9] P. Biginelli, Aldehyde-urea derivatives of aceto-and oxaloacetic acids, Gazz. Chim. Ital. 23 (1893) 360-413.
10. [10]
  [10] S. Chitra, K. Pandiarajan, Calcium fluoride: an efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)thione: an improved high yielding protocol for the Biginelli reaction, Tetrahedron Lett. 50 (2009) 2222-2224.
11. [11]
  [11] A. Debache, M. Amimour, A. Belfaitah, et al., A one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by triphenylphosphine as Lewis base, Tetrahedron Lett. 49 (2008) 6119-6121.
12. [12]
  [12] E.H. Hu, D.R. Sidler, U.H. Dolling, Unprecedented catalytic three component one-pot condensation reaction: an efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones, J. Org. Chem. 63 (1998) 3454-3457.
13. [13]
  [13] J. Lu, H. Ma, Iron(III)-catalyzed synthesis of dihydropyrimidinones, improved conditions for the Biginelli reaction, Synlett (2000) 63-64.
14. [14]
  [14] C.R. Brindaban, A. Hajra, U. Jana, Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the Biginelli reaction, J. Org. Chem. 65 (2000) 6270-6272.
15. [15]
  [15] H. Zhang, Z. Zhou, Z. Yao, et al., Efficient synthesis of pyrimidinone derivatives by ytterbium chloride catalyzed Biginelli-type reaction under solvent-free conditions, Tetrahedron Lett. 50 (2009) 1622-1624.
16. [16]
  [16] K. Ramalinga, P. Vijayalakshmi, T.N.B. Kaimal, Bismuth(III)-catalyzed synthesis of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction, Synlett 6 (2001) 863-865.
17. [17]
  [17] J.T. Starcevich, T.J. Laughlin, R.S. Mohan, Iron(III) tosylate catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction, Tetrahedron Lett. 54 (2013) 983-985.
18. [18]
  [18] Y. Qiu, H. Sun, Z. Ma, et al., Efficient, stable, and reusable Lewis acid-surfactantcombined catalyst: one-pot Biginelli and solvent-free esterification reactions, J. Mol. Catal. A: Chem. 392 (2014) 76-82.
19. [19]
  [19] J. Svetlik, V. Kettmann, The chameleon-like behaviour of 3-amino-1,2,4-triazole in the Biginelli reaction: unexpected formation of a novel spiroheterocyclic system, Tetrahedron Lett. 52 (2011) 1062-1066.
20. [20]
  [20] I. Couto, I. Tellitu, E. Dominguez, Searching for a direct preparation of dihydropyrimidine-5-carboxamides under Biginelli reaction conditions, Arkivoc II (2011) 115-126.
21. [21]
  [21] F. Makaev, E. Styngach, V. Shargarovskii, et al., Imidazolium salts with a free carboxy group as new catalysts of the Biginelli reaction, Russ. J. Org. Chem. 46 (2010) 616-617.
22. [22]
  [22] W.Y. Chen, S.D. Qin, J.R. Jin, Efficient Biginelli reaction catalyzed by sulfamic acid or silica sulfuric acid under solvent-free conditions, Syn. Commun. 37 (2007) 47-52.
23. [23]
  [23] P.N. Reddy, Y.T. Reddy, M.N. Reddy, et al., Cellulose sulfuric acid: an efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-ones, Syn. Commun. 39 (2009) 1257-1263.
24. [24]
  [24] S.R. Jetti, A. Bhatewara, T. Kadre, et al., Silica-bonded N-propyl sulfamic acid as an efficient recyclable catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under heterogeneous conditions, Chin. Chem. Lett. 25 (2014) 469-473.
25. [25]
  [25] H. Kiyani, M. Ghiasi, Potassium phthalimide: an efficient and green organocatalyst for the synthesis of 4-aryl-7-(arylmethylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-ones/thionesunder solvent-free conditions,Chin.Chem.Lett. 25 (2014) 313-316.
26. [26]
  [26] J. Gui, D. Liu, C. Wang, et al., One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by acidic ionic liquids under solvent-free condition, Synth. Commun. 39 (2009) 3436-3443.
27. [27]
  [27] A.R.M. Zare, M.A. Zolfigol, M. Zarei, et al., Design, characterization and application of new ionic liquid 1-sulfopyridinium chloride as an efficient catalyst for tandem Knoevenagel-Michael reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with aldehydes, Appl. Catal. A 467 (2013) 61-68.
28. [28]
  [28] B. Janardhan, B. Rajitha, A. Peter, Crooks poly(4-vinylpyridinium) hydrogen sulfate: an efficient and recyclable Bronsted acid catalyst for the synthesis of fused 3,4-dihydropyrimidin-2(1H)-ones and thiones, J. Saudi Chem. Soc. (2013), http://dx.doi.org/10.1016/j.jscs.2012.10.007.
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1.
沈阳化工大学材料科学与工程学院沈阳 110142