A facile approach for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones using a microwave promoted Biginelli protocol in ionic liquid

Journal of Chemical Sciences

Volumn 124, Issue 4, 2012, Pages 921-926

  Dadhania, Abhishek N ^a   Patel, Vaibhav K ^a   Raval, Dipak K ^a  

^a SARDAR PATEL UNIVERSITY   (India)

Author keywords

Biginelli reaction; Ionic liquid; Microwave irradiation; Recyclability

Indexed keywords

IRRADIATION; LIQUIDS; MICROWAVE IRRADIATION; MICROWAVES;

BIGINELLI COMPOUNDS; BIGINELLI REACTION; FUNCTIONALIZED IONIC LIQUIDS; GREEN CATALYSTS; HETEROCYCLES; HIGH YIELD; ONE-POT SYNTHESIS; RECYCLABILITY;

IONIC LIQUIDS;

EID: 84867156113     PISSN: 09743626     EISSN: 09737103     Source Type: Journal    
DOI: 10.1007/s12039-012-0278-5     Document Type: Article

References (53)

1. Kappe C O 1993 Tetrahedron 49 6937
2. Cho H, Ueda M, Shima K, Mizuno A, Hayashimatsu M, Ohnaka Y, Takeuchi Y, Hamaguchi M and Aisaka K 1989 J. Med. Chem. 32 2399;
3. Atwal K S, Rovnyak G C, Kimball S D, Floyd D M, Moreland S, Swanson B N, Gougoutas J Z, Schwartz J, Smillie K M and Malley M F 1990 J. Med. Chem. 33 2629;
4. Rovnyak G C, Kimball S D, Beyer B, Cucinotta G, Di Marco J D, Gougoutas J, Hedberg A, Malley M and McCarthy J P 1995 J. Med. Chem. 38 119
5. Atwal K S, Swanson B N, Unger S E, Floyd D M, Moreland S, Hedberg A and O'Reilly B C 1991 J. Med. Chem. 34 806;
6. Rovnyak G C, Atwal K S, Hedberg A, Kimball S D, Moreland S, Gougoutas J Z, O'Reilly B C, Schwartz J and Malley M F 1992 J. Med. Chem. 35 3254;
7. 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
8. Wong W C, Lagu B, Nagarathnam D, Marzabadi M R and Gluchowski C PCT Int. Appl. WO 97 42, 956 and WO 98 51, 311;
9. Nagarathnam D, Wong W C, Miao SW, Patane M A and Gluchowski C PCT Int. Appl. WO 97 17, 969;
10. Sidler D R, Larsen R D, Chartrain M, Ikemoto N, Roberge C M, Taylor C S, Li W and Bills G F PCT Int. WO 99 07695
11. Bruce M A, Pointdexter G S, Johnson G PCT Int. Appl. WO 98 33, 791
12. Snider B B and Shi Z 1993 J. Org. Chem. 58 3828
13. Biginelli P 1893 Gazz. Chim. Ital. 23 360
14. Bigi F, Carloni S, Frullanti B, Maggi R and Sartori G 1999 Tetrahedron Lett. 40 3465;
15. Kappe C O and Falsone S F 1998 Synlett. 718;
16. Hu E H, Sidler D R and Dolling U-H 1998 J. Org. Chem. 63 3454
17. Oreilly B C and Atwal K S 1987 Heterocycles 26 1185;
18. Atwal K S, Oreilly B C, Gougoutas J Z and Malley M F 1987 Heterocycles 26 1189;
19. Shutalev A D and Kuksa V A 1997 Khim geterotsikl+ 105;
20. Shutalev A D, Kishko E A, Sivova N V and Kuznetsov A Y 1998 Molecules 3 100;
21. Rani V R, Srinivas N, Kishan M R, Kulkarni S J and Raghavan K V 2001 Green Chem. 3 305;
22. Lu J, Bai Y, Wang Z, Yang B and Ma H 2000 Tetrahedron Lett. 41 9075;
23. Ma Y, Qian C, Wang L and Yang M 2000 J. Org. Chem. 65 3864;
24. Ranu B C, Hajra A and Jana U 2000 J. Org. Chem. 65 6270
25. Yadav J S, Reddy B V S, Reddy E J and Ramalingam T 2000 J. Chem. Res., Synop. 354
26. Mukhopadhyay C, Datta A and Banik B K 2007 J. Heterocycl. Chem. 44 979
27. Mishra B G, Kumar D and Rao V S 2006 Catal. Commun. 7 457
28. Pisani L, Prokopcová H, Kremsner J M and Kappe C O 2007 J. Comb. Chem. 9 415
29. Polshettiwar V and Varma R S 2007 Tetrahedron Lett. 48 7343
30. Saxena I, Borah D C and Sarma J C 2005 Tetrahedron Lett. 46 1159
31. Kumar D, Sundaree M S and Mishra B G 2006 Chem. Lett. 35 1074
32. Kapoor K K, Ganai B A, Kumar S and Andotra C S 2006 Can. J. Chem. 84 433
33. Tu S J, Fang F, Miao C B, Jiang H and Shi D Q 2003 Chin. J. Chem. 21 706
34. Hazarkhani H and Karimi B 2004 Synthesis 1239
35. Shanmugam P, Annie G and Perumal P T 2003 J. Heterocycl. Chem. 40 879
36. Liang B, Wang X, Wang J-X and Du Z 2007 Tetrahedron 63 1981
37. Kappe C O 2002 Curr. Opin. Chem. Biol. 6 314;
38. Oliver Kappe C 2008 Chem. Soc. Rev. 37 1127
39. Yi F, Peng Y and Song G 2005 Tetrahedron Lett. 46 3931;
40. Zare A, Hasaninejad A, Khalafi-Nezhad A, Moosavi Zare A R and Parhami A 2007 Arkivoc 2007 105
41. Welton T 1999 Chem. Rev. 99 2071
42. Kappe C O 2008 Chem. Soc. Rev. 37 1127
43. Li J, Peng Y and Song G 2005 Catal. Lett. 102 3
44. Dadhania A N, Patel V K and Raval D K 2011 J. Braz. Chem. Soc. 22 511
45. Fu N-Y, Yuan Y-F, Cao Z, Wang S-W, Wang J-T and Peppe C 2002 Tetrahedron 58 4801
46. Chari M A, Shobha D, Kumar T K and Dubey P K 2005 arkivoc xv 74
47. Paraskar A S, Dewkar G K and Sudalai A 2003 Tetrahedron Lett. 44 3305
48. Reddy C V, Mahesh M, Raju P V K, Babu T R and Reddy V V N 2002 Tetrahedron Lett. 43 2657
49. Gholap A R, Venkatesan K, Daniel T, Lahoti R J and Srinivasan K V 2004 Green Chem. 6 147
50. Pasunooti K K, Chai H, Jensen C N, Gorityala B K, Wang S and Liu X-W 2011 Tetrahedron Lett. 52 80
51. Garima, Srivastava V P and Yadav L D S 2010 Tetrahedron Lett. 51 6436
52. Rosi Reddy K, Venkateshwar Reddy C, Mahesh M, Raju P V K and Narayana Reddy V V 2003 Tetrahedron Lett. 44 8173
53. Shanmugam P, Annie G and Perumal P T 2003 J. Heterocycl. Chem. 40 879