Skip to main content
Log in

Synthesis of New dihydropyrimidinones catalysed by dicationic ionic liquid

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

A convenient multi step synthetic protocol for new dihydropyrimidinones bearing quinolynyl methoxy phenyl moiety has been developed from 2-chloro-3-formyl quinolines. The last step is one-pot Biginelli reaction of multicomponents, 4-((2-chloroquinolin-3-yl) methoxy) benzaldehydes, ethyl acetoacetate and urea mediated and catalysed by dicationic ionic liquid (3-methyl-1-[3-(methyl-1H-imidazolium-1-yl) propyl]-1H-imidazolium dibromide (C3 [min]2 2 [Br − ] )). Simple work-up procedures and moderate to good yields of the pyrimidinones and the intermediates are the merits of the route.

A convenient multistep synthetic protocol for new dihydropyrimidinones bearing quinolynyl methoxy phenyl moiety has been developed from 2-chloro-3-formyl quinolines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. (a) Kappe C O, 2000 Acc. Chem. Res. 49 879; (b) Kappe C O 1993 Tetrahedron 49 37; (c) Biginelli, P. 1893 Ber. 26 447

  2. (a) Rovnyak G C, Atwal K S, Hedberg A, Kimball S D, Moreland S, Gougoutas J Z, OReilly B C, and Malley M F 1992 J. Med. Chem. 35 3254; (b) Cho H, Ueda M, Shima K, Mizuno A, Ohnaka M, Takeuchi Y, Hamaguchi Y, Aisaka M K, Hidaka T, Kawai M, Takeda M, Ishihara T, Funahashi K, Satoh F, Morita M, and Noguchi T 1989 J. Med. Chem. 32 2399

    Google Scholar 

  3. (a) Atwal K S, Swanson B N, Unger S E, Floyd D M, Moreland S, Hedberg A, and OReilly B C 1991 J. Med. Chem. 34 806; (b) Grover G J, Dzwonczyk S, McMullen D M, Normandin D E, Parham C S, Sleph P G, and Moreland S 1995 J. Cardiovasc. Pharmacol. 26 289

  4. (a) Mayer T U, Kapoor T M, Haggarty S J, King R W, Schreiber S L, Mitchison T J 1999 Science 286 971; (b) Haggarty S J, Mayer T U, Miyamoto D T, Fathi R, King R W, Mitchson T J and Schreiber S L 2000 Chem. Biol. 7 268

  5. Tewari N, Tiwari V K, Mishra R C, Tripathi R P A, Srivastava K, Ahmad R R, Srivastava B. S. 2003 Bioorg. Med. Lett. 11 2911

    CAS  Google Scholar 

  6. Snider B B and Shi Z 1993 J. Org. Chem. 58 3828, and refs cited therein

    Article  CAS  Google Scholar 

  7. (a) Patil A D, Kumar N V, Kokke W C, Bean M, Freyer F A J, Brosse De C, Mai S, Truneh A and Faulkner D J 1995 J. Org. Chem. 60 1182; (b) Snider B B, Chen J, Patil A D and Freyer A 1996 Tetrahedron Lett. 37 6977; (c) Rama Rao A V, Gurjar M K and Vasudevan J 1995 J. Chem. Soc. Chem. Commun. 1369

    Google Scholar 

  8. Gubert S, Braojos C, Anglada L, Bolos J and Pllacin C 1992 J. Heterocycl. Chem. 29 55

    Article  CAS  Google Scholar 

  9. Alhaider A A, Adbekader M A and Lien E J 1985 J. Med. Chem. 28 1394

    Article  CAS  Google Scholar 

  10. Cai W, Xu D and Yiyao G 1987 18 62; Chem. Abstr. 107 1987 236651v.

    Google Scholar 

  11. Edmont D, Rocher R, Plisson C and Chenault J 2000 Bioorg. Med. Chem. Lett. 10 1831

    Article  CAS  Google Scholar 

  12. Cantello B C C, Cawthrone M A, Cottam G P, Duff P T, Haigh D, Hindley R M, Lister C A, Smith S A and Thurlby P L 1994 J. Med. Chem. 37 3977

    Article  CAS  Google Scholar 

  13. Cantello B C C, Cawthrone M A, Haigh D, Hindley R M, Smith S A and Thurlby P L 1994 Bioorg. Med. Chem. Lett. 4 1181

    Article  CAS  Google Scholar 

  14. (a) Folkers K and Johnson T B 1933 J. Am. Chem. Soc. 55 2886; (b) Folkers K and Johnson T B 1933 J. Am. Chem. Soc. 55 3784

  15. Hu E H, Sidler D R and Dolling U 1998 J. Org. Chem. 63 3454

    Article  CAS  Google Scholar 

  16. Kappe C O and Falsone S F 1998 Synlett. 718

  17. Bigi F, Carloni S, Frullanti B, Maggi R and Sartori G 1999 Tetrahedron Lett. 40 3465

    Article  CAS  Google Scholar 

  18. (a) Radha Rani V, Srinivas N, Krishnan R M, Kulkarni S J and Raghavan K V 2001 Green Chem. 3 305; (b) Murata H, Ishitani H and Iwamoto M 2010 Org. Biomol. Chem. 8 1202

  19. Lu J and Ma H 2000 Synlett. 63

  20. Ma Y, Qian C, Wang L and Yang M 2000 J. Org. Chem. 65 3864

    Article  CAS  Google Scholar 

  21. Varala R, Alam M M and Adapa S R 2003 Synlett. 67

  22. Gohain M, Prajapati D and Sandhu J S 2004 Synlett. 235

  23. Rodrı JC and Kirsch G 2007 Tetrahedron Lett. 48 5777

    Article  Google Scholar 

  24. (a) Rafiee E and Jafari H 2006 Bioorg. Med. Chem. Lett. 16 2463; (b) Amini M M, Shaabani A and Bazgir A 2006 Catal. Commun. 7 843; (c) Maradur P S and Gokavi G, S 2007 Catal. Commun. 8 279; (d) Heravi M M, Bakhtiari K and Bamoharram F F 2006 Catal. Commun. 7 373

  25. (a) Joseph J K, Jain S L, Sain B 2006 J. Mol. Catal. A: Chem. 247 99; (b) Palaniappan S and John A 2005 J. Mol. Catal. A: Chem. 233 9

    Google Scholar 

  26. (a) Chen X H, Xu X Y, Liu H, Cun L F and Gong L Z 2006 J. Am. Chem. Soc. 128 14802; (b) Li N, Chen X-H, Song J, Luo S-W, Fan W and Gong L-Z 2009 J. Am. Chem. Soc. 131 15301

  27. Ahmed E L and Johan 2007 Tetrahedron Lett. 48 5407

    Article  CAS  Google Scholar 

  28. Zumpe F L, Flu M, Schmitz K, Lender A. 2007 Tetrahedron Lett. 48 1421

    Article  CAS  Google Scholar 

  29. Zhu Y L, Huang S L, Wan J P, Yan L, Pan Y J and Wu A 2006 Org. Lett. 8 2599

    Article  CAS  Google Scholar 

  30. Wang D C and Rong Q G 2010 Sync. Commun. 40 1115

    Article  CAS  Google Scholar 

  31. Ranu B C and Hajra A U 2000 J. Org. Chem. 65 6270

    Article  CAS  Google Scholar 

  32. Bose D S, Fatima L and Mereyala H B 2003 J. Org. Chem. 68 587

    Article  CAS  Google Scholar 

  33. Yang Y F C 2005 J. Am. Chem. Soc. 127 16386

    Article  Google Scholar 

  34. (a) Gholap A R, Venkatesan K, Daniel T, Lahoti R J and Srinivasan K V 2004 Green Chem. 6 147; (b) Dong F, Jun L, Xinli Z, Zhiwen Y and Zuliang L 2007 J. Mol. Catal. A: Chem. 274 208; (c) Peng J and Deng, Y. 2001 Tetrahedron Lett. 59 175; (d) Minga L, Wei-Si G, Li-Rong W, Y-Feng L and Hua-Zheng Y 2006 J. Mol. Catal. A: Chem. 258 133; (e) Shaabani A, Sarvary A, Rahmati A and Rezayan A H 2007 Lett. Org. Chem. 4 68

  35. Shen Z L X P and Ji S J 2010 J. Org. Chem. 75 1162

    Article  CAS  Google Scholar 

  36. (a) Kappe C O and Varma R S 1999 Synthesis 1799; (b) Yadav J S, Reddy V S, Reddy E J, and Ramalingam T 2000 J. Chem. Res. (S) 354; (c) Stefani H A and Gatti P M 2000 Synth. Commun. 30 2165

  37. (a) Yadav J S, Reddy B V S, Reddy K B, Raj K S and Prasad A R 2001 J. Chem. Soc. Perkin Trans. 1 1939; (b) Li J T, Han J F, Yang J H and Li T S 2003 Ultrason Sonochem. 10 119

  38. (a) Studer A, Jeger P, Wipf P and Curran D P 1997 J. Org. Chem. 62 2917; (b) Kappe C O 2000 Bioorg. Med. Chem. Lett. 10 49

  39. Welton T 1999 Chem. Rev. 99 2071

    Article  CAS  Google Scholar 

  40. Wilkes J S and Zaworotko M J 1992 J. Chem. Soc. Chem. Commun. 965

  41. (a) Holbrey J D and Seddon K R 1999 Clean Prod. Proces. 1 223; (b) Huddleston J G, Willauer H D, Swatloski R P, Visser A E and Rogers R D 1998 Chem. Commun. 1765

  42. (a) Wasserscheid P and Keim W 2000 Angew. Chem. Int. Ed. 39 3772; (b) Dupont J, De Souza R F and Suarez A Z 2002 Chem. Rev. 102 3667; (c) Ionic liquids in synthesis, P Wasserscheid and Welton T (eds) Weinheim: Wiley-VCH, 2003.

  43. (a) Fukumoto K, Yoshizawa M, Ohno H 2005 J. Am. Chem. Soc. 127 2398; (b) Zhou Z B, Matsumoto H and Tatsumi K 2005 Chem. Eur. J. 11 752; (c) Branco L C, Rosa J N, Ramos J J M and Afonso A M 2002 Chem. Eur. J. 8 3671.

  44. (a) Anderson J L, Ding R, Ellern A and Armstrong D W 2005 J. Am. Chem. Soc. 127 593; (b) Han W, Armstrong D W 2005 Org. Lett. 7 4205

  45. (a) Ugi I, Domling A and Horl W 1994 Endeavour 18 115; (b) Armstrong R W, Combs A P, Tempest P A, Brown S D and Keating T A 1996 Acc. Chem. Res. 29 123; (c) Tietze L F and Lieb M E 1998 Curr. Opin. Chem. Biol. 2 363; (d) Dax S L, McNally J J and Youngman M A 1999 Curr. Med. Chem. 6 255; (e) Domling A 1998 High Throughput Screening 1 1

  46. Bienayme H, Hulme C, Oddon G and Schmitt P 2000 Chem. Eur. J. 6 3321

    Article  CAS  Google Scholar 

  47. (a) Mahalle S R, Netankar P D, Bondge S P and Mane R A 2008 Green Chem. Lett. Rev. 2 103; (b) Pratap U R, Mali J R, Jawale D V and Mane R A 2009 Tetrahedron Lett. 50 1352; (c) Mali J R, Pratap U R, Netankar P D and Mane R A 2009 Tetrahedron Lett. 50 5025; (d) Jawale D V, Lingampalle D L, Pratap U R and Mane R A 2010 Chine. Chem. Lett. 21 412; (e) Lingampalle D, Jawale D, Waghmare R and Mane R 2010 Synth. Commun. 40 2397; (f) Mali J R, Pratap U R, Jawale D V and Mane R A 2010 Tetrahedron Lett. 51 3980

  48. (a) Amini M M, Shaabani A and Bazgir 2006 A Catal. Commun. 7 843; (b) Hu E H, Sidler D R and Dolling U H 1998 J. Org. Chem. 63 3454

  49. (a) Meth-Cohn O, Narine B and Tarnowski B 1981 J. Chem. Soc. Perkin Trans. 1 1520; (b) Bekhit A Am, El-Sayed O A, Aboulmagd E and Park J Y 2004 Eur. J. Med. Chem. 39 249

  50. Pokalwar R U, Hangarge R V, Kategaonkar A H and Shingare M S. 2009 Russian J. Org. Chem. 45 430

    Article  CAS  Google Scholar 

  51. Varma R S and Vasudevan V N 2002 Org. Lett. 4 3161

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to RAMRAO A MANE.

Rights and permissions

Reprints and permissions

About this article

Cite this article

JAWALE, D.V., PRATAP, U.R., MULAY, A.A. et al. Synthesis of New dihydropyrimidinones catalysed by dicationic ionic liquid. J Chem Sci 123, 645–655 (2011). https://doi.org/10.1007/s12039-011-0127-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-011-0127-y

Keywords

Navigation