Microwave-promoted alkynylation-cyclization of 2-aminoaryl ketones: A green strategy for the synthesis of 2,4-disubstituted quinolines

Synlett

Volumn , Issue 20, 2010, Pages 3104-3112

  Mohammadpoor Baltork, Iraj ^a   Tangestaninejad, Shahram ^a   Moghadam, Majid ^a   Mirkhani, Valiollah ^a   Anvar, Salma ^a   Mirjafari, Arsalan ^a  

^a UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

microwave irradiation; 2,4 disubstituted quinolines; 2 aminoaryl ketones; arylacetylenes; K5CoW12O 403H2O

Indexed keywords

2 AMINOARYLKETONE DERIVATIVE; 2,4 DISUBSTITUTED QUINOLINE; CHLOROQUINE; KETONE DERIVATIVE; QUININE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; GREEN CHEMISTRY; MICROWAVE RADIATION; RECYCLING; SOLVENT EXTRACTION;

EID: 78650177754     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259065     Document Type: Article

References (53)

1. Zhu H, Yang R F., Yun L H., Li J, Chin. Chem. Lett. 2010 21 35
2. Bernotas R C., Singhaus R R., Kaufman D H., Bioorg. Med. Chem. Lett. 2010 20 209
3. Godell J R., Puig-Basagoiti F, Forshey B M., Shi P Y., Ferguson D M., J. Med. Chem. 2006 49 2127
4. ODonnell F, Smyth T J. P., Ramachandran V N., Int. J. Antimicrob. Agents 2010 35 30
5. Balamurugan K, Jeyachandran V, Perumal S, Eur. J. Med. Chem. 2010 45 682
6. Nogueira F, Diez A, Radfar A, Pérez-Benavente S, Puyet A, Bautista J, Acta Tropica 2010 114 109
7. Tong H, Wang L, Jing X, Wang F, Macromolecules 2003 36 2584
8. Tumambac G E., Rosencrance C M., Wolf C, Tetrahedron 2004 60 1293
9. Skraup Z H., Monatsh. Chem. 1881 2 139
10. DePaolis O D., Teixeira L, Török B, Tetrahedron Lett. 2009 50 2939
11. Skraup Z H., Ber. Dtsch. Chem. Ges. 1882 15 897
12. Doebner O, Miller W, Ber. Dtsch. Chem. Ges. 1881 14 2812
13. Doebner O, Miller W, Ber. Dtsch. Chem. Ges. 1883 16 2464
14. Sivaprasad G, Rajesh R, Perumal P T., Tetrahedron Lett. 2006 47 1783
15. Friedländer P, Ber. Dtsch. Chem. Ges. 1882 15 2572
16. Arcadi A, Chiarini M, Di Giuseppe S, Marinelli F, Synlett 2003 203
17. Yadav J S., Reddy B V. S., Sreedhar P, Rao R S., Nagaiah K, Synthesis 2004 2381
18. Das B, Damodar K, Chowdhury N, Kumar R A., [nl] J. Mol. Catal. A: Chem. 2007 274 148
19. Combes A, Bull. Soc. Chim. Fr. 1888 49 89
20. Johnson W S., Matthews F J., J. Am. Chem. Soc. 1944 66 210
21. Quiroga J, Trilleras J, Insuasty B, Abonia R, Negueras M, Marchal A, Cobo J, Tetrahedron Lett. 2010 51 1107
22. Born J, J. Org. Chem. 1972 37 3952
23. Liu X Y., Ding P, Huang J S., Che C M., Org. Lett. 2007 9 2645
24. Mierde H V., DerVoort P V., Verpoort F, Tetrahedron Lett. 2008 49 6893
25. Xiao F, Chen Y, Liu Y, Wang J, Tetrahedron 2008 64 2755
26. Rotzoll S, Willy B, Schönhaber J, Rominger F, Müller T J. J., Eur. J. Org. Chem. 2010 3516
27. Horn J, Marsden S P., Nelson A, House D, Weingarten G G., Org. Lett. 2008 10 4117
28. Kulkarni A, Török B, Green Chem. 2010 12 875
29. Korivi R P., Cheng C, J. Org. Chem. 2006 71 7079
30. Leardini R, Nanni D, Tundo A, Zanardi G, Ruggieri F, J. Org. Chem. 1992 57 1843
31. Fan X, Zhang W, Tetrahedron Lett. 2002 43 7001
32. Park D J., Fulmer T D., Beam C F., J. Heterocycl. Chem. 1981 18 649
33. Gabriele B, Mancuso R, Salerno G, Ruffolo G, Plastina P, J. Org. Chem. 2007 72 6873
34. Molina P, Alajarin M, Sanchez-Andrada P, Synthesis 1993 225
35. Lekhok K C., Prajapati D, Boruah R C., Synlett 2008 655
36. Sarma R, Prajapati D, Synlett 2008 3001
37. Firouzabadi H, Jafari A A., Curr. Org. Chem. 2008 12 233
38. Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, Mirkhani V, Hojati S F., Catal. Commun. 2008 9 1153
39. Torviso R, Mansilla D, Belizan A, Alesso E, Moltrasio G, Vazquez P, Pizzio L, Blanco M, Caceres C, Appl. Catal., A 2008 339 53
40. Mizuno N, Misono M, Chem. Rev. 1998 98 199
41. Chester A W., J. Org. Chem. 1970 35 1797
42. Rafiee E, Tangestaninejad S, Habibi M H., Mirkhani V, Bioorg. Med. Chem. Lett. 2004 14 3611
43. Saha S K., Ali M, Banerjee P, Coord. Chem. Rev. 1993 122 41
44. Weinstock I A., Chem. Rev. 1998 98 113
45. Habibi M H., Tangestaninejad S, Mohammadpoor-Baltork I, Mirkhani V, Yadollahi B, Tetrahedron Lett. 2001 42 2851
46. Firouzabadi H, Jafari A A., J. Iran. Chem. Soc. 2005 2 85
47. Kantevari V C., Chary M V., Vuppalapati S V. N., Tetrahedron 2007 63 13024
48. Tangestaninejad S, Mirkhani V, Moghadam M, Mohammadpoor-Baltork I, Shams E, Salavati H, Catal. Commun. 2008 9 1001
49. Nagarapu L, Apuri S, Gaddam S, Bantu R, Mahankhali V C., Kantevari S, Lett. Org. Chem. 2008 5 60
50. Nagarapu L, Kantevari S, Cheemalapati V N., Apuri S, Kumari N V., J. Mol. Catal. A: Chem. 2007 264 22
51. Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, Mirkhani V, Eskandari Z, Ultrason. Sonochem. 2010 17 857
52. Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork I, Khajehzadeh M, Monatsh. Chem. 2010 141 641
53. Mirjafari A, Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, Mirkhani V, Khosropour A R., Tetrahedron Lett. 2010 51 3274