A Multicomponent, Catalyst-free, One-Pot Synthesis of Functionalized 1,4-Dihydroquinolines and Their Antimicrobial Studies

Journal of Heterocyclic Chemistry

Volumn 52, Issue 5, 2015, Pages 1302-1307

  Chidurala, Praveen ^a   Jetti, Venkateshwarlu ^a   Pagadala, Ramakanth ^b   Meshram, Jyotsna S ^a   Jonnalagadda, Sreekantha B ^b  

^a RTM NAGPUR UNIVERSITY   (India)

^b UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

1, 4 dihydro quinolines; classical method; microwave method; multi component reaction

Indexed keywords

1,4 DIHYDRO 5 HYDROXY 2 METHYL 4 (3 NITROPHENYL) N PHENYLQUINOLINE 3 CARBOXAMIDE; 1,4 DIHYDRO 5 HYDROXY 2 METHYL 4 (4 NITROPHENYL) N PHENYLQUINOLINE 3 CARBOXAMIDE; 1,4 DIHYDRO 5 HYDROXY 2 METHYL N 4 4 TOLYLQUINOLINE 3 CARBOXAMIDE; 1,4 DIHYDRO 5 HYDROXY 2 METHYL N PHENYL 4 3 TOLYLQUINOLINE 3 CARBOXAMIDE; 1,4 DIHYDRO 5 HYDROXY 2 METHYL N,4 DIPHENYLQUINOLINE 3 CARBOXAMIDE; 1,4 DIHYDRO 5 HYDROXY 4 (4 HYDROXYPHENYL) 2 METHYL N PHENYLQUINOLINE 3 CARBOXAMIDE; 1,4 DIHYDRO 5 HYDROXY 4 (4 METHOXYPHENYL) 2 METHYL N PHENYLQUINOLINE 3 CARBOXAMIDE; 4 (3 CHLOROPHENYL) 1,4 DIHYDRO 5 HYDROXY 2 METHYL N PHENYLQUINOLINE 3 CARBOXAMIDE; 4 (FURAN 2 YL) 1,4 DIHYDRO 5 HYDROXY 2 METHYL N PHENYLQUINOLINE 3 CARBOXAMIDE; 4 [4 (DIMETHYLAMINO)PHENYL] 1,4 DIHYDRO 5 HYDROXY 2 METHYL N PHENYLQUINOLINE 3 CARBOXAMIDE; ALDEHYDE; AMMONIUM ACETATE; AMPICILLIN; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; DIHYDROQUINOLINE DERIVATIVE; NYSTATIN; RESORCINOL; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; ASPERGILLUS NIGER; BACILLUS SUBTILIS; BACTERIAL GROWTH; CONTROLLED STUDY; DRUG SYNTHESIS; ESCHERICHIA COLI; INHIBITION ZONE; KLEBSIELLA PNEUMONIAE; MICROWAVE IRRADIATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; ONE POT SYNTHESIS; PROTEUS VULGARIS; STAPHYLOCOCCUS AUREUS; TRICHODERMA;

EID: 84942551969     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.2230     Document Type: Article

References (58)

1. (a), Ugi, I.,;, Domling, A., Angew Chem Int Ed 2000, 39, 3168;
2. (b), Tietze, L. F.,;, Modi, A., Med Res Rev 2000, 20, 304;
3. (c), Ugi, I.,;, Domling, A.,;, Werner, B., J Heterocycl Chem 2000, 37, 647.
4. (a), Pirrung, M. C.,;, Sarma, K. D., J Am Chem Soc 2004, 126, 444;
5. (b), Da Silva, E. N., Res J Chem Environ 2007, 11, 90.
6. (a), Benetti, S.,;, Romagnoli, R.,;, De Risi, C.,;, Spalluto, G.,;, Zanirato, V., Chem Rev 1995, 95, 1065;
7. (b), Langer, P., Chem Eur J 2001, 7, 3858;
8. (c), Langer, P., Synthesis 2002, 441;
9. (d), Simon, C.,;, Constantieux, T.,;, Rodriguez, J., Eur J Org Chem 2004, 4957.
10. (a), Ramakanth, P.,;, Suresh, M.,;, Venkata, D. B. C. D.,;, Sreekantha, B. J., Cat Comm 2014, 45, 148;
11. (b), Ramakanth, P.,;, Suresh, M.,;, Surjyakanta, R.,;, Sreekantha, B. J., RSC Adv 2014, 4, 6602;
12. (c), Ramakanth, P.,;, Suresh, M.,;, Sreekantha, B., J Ultrasonics Sonochem 2013, 21, 472;
13. (d), Toure, B. B.,;, Hall, D. G., Chem Rev 2009, 109, 4439;
14. (e), Sunderhaus, J. D.,;, Martin, S. F., Chem Eur J 2009, 15, 1300;
15. f(f), Ganem, B., Acc Chem Res 2009, 42, 463;
16. (g), Ismabery, N.,;, Lavila, R., Chem Eur J 2008, 14, 8444;
17. (h), Jang, B.,;, Shi, F.,;, Tu, S. T., Curr Org Chem 2010, 14, 357.
18. (a), Doling, A., Chem Rev 2006, 106, 17;
19. (b), Yu, J.,;, Shi, F.,;, Gong, L. Z., Acc Chem Res 2011, 44, 1156;
20. (c), Domling, A.,;, Wang, W.,;, Wang, K., Chem Rev 2012, 112, 3083;
21. (d), Eckert, H., Molecules 2012, 17, 1074.
22. (a), Balme, G.,;, Bossharth, E.,;, Monteiro, N., Eur J Org Chem 2003, 4101;
23. (b), Orru, R. V. A.,;, Greef, M. D., Synthesis 2003, 1471;
24. (c), Bienayme, H.,;, Hulme, C.,;, Oddon, G.,; Schmitt, P Chem-Eur J 2000, 6, 3321;
25. (d), Grondal, C.,;, Jeanty, M.,;, Enders, D., Nat Chem 2010, 2, 167;
26. (e), Nicolaou, K. C.,;, Edmonds, D. J.,;, Bulger, P. G., Angew Chem Int Ed 2006, 45, 7134.
27. (a), Michael, J. P., Nat Prod Rep 1997, 14, 605;
28. (b), Gantier, J. C.,;, Fournet, A.,;, Munos, M. H.,;, Hocquemiller, R., Planta Med 1996, 62, 285;
29. (c), Michael, J. P., Nat Prod Rep 2007, 24, 223;
30. (d), Michael, J. P., Nat Prod Rep 2005, 22, 627;
31. (e), Bilker, O.,;, Lindo, V.,;, Panico, M.,;, Etiene, A. E.,;, Paxton, T.,;, Dell, A.,;, Rogers, M.,;, Sinden, R. E.,;, Morris, H. R., Nature 1998, 392, 289.
32. Patel, P. N.,;, Patel, K. D.,;, Patel, H. S., Chin Chem Lett 2011, 22, 1297.
33. Eswaran, S.,;, Adhikari, A. V.,;, Kumar, R. A., Eur J Med Chem 2010, 45, 957.
34. Kaur, K.,;, Jain, M.,;, Reddy, R. P.,;, Jain, R., Eur J Med Chem 2010, 45, 3245.
35. Leatham, P. A.,;, Bird, H. A.,;, Wright, V., Eur J Rheumatol Inflamm 1983, 6, 209.
36. Zhang, F.,;, Zhai, X.,;, Chen, L. J., et al., Chin Chem Lett 2011, 22, 1277.
37. Muruganantham, N.,;, Sivakumar, R.,;, Anbalagan, N., et al., Biol Pharm Bull 2004, 27, 1683.
38. Maguire, M. P.,;, Sheets, K. R.,;, McVety, K., et al., J Med Chem 1994, 37, 2129.
39. Z. G.,;, Zeng, C. C.,;, Yang, L. F., et al., Chin Chem Lett 2009, 20, 789.
40. Satio, I.,;, Sando, S.,;, Nakatani, K., Bioorg Med Chem 2001, 9, 2381.
41. Kappe, C. O., Angew Chem Int Ed 2004, 43, 6250.
42. C. R.,;, Varma, R. S., Top Curr Chem 2006, 266, 199.
43. Hantzsch, A.,. Chem Ber 1881, 14, 1637.
44. Debache, A.,;, Ghalem, W.,;, Boulcina, R.,;, Belfaitah, A.,;, Rhouati, S.,;, Carboni, B., Tetrahedron Lett 2009, 50, 5248.
45. Ko, S.,;, Sastry, M. N. V.,;, Lin, C.,;, Yao, C. F., Tetrahedron Lett 2005, 46, 5771.
46. Kumar, A.,;, Maurya, R. A., Tetrahedron Lett, 2007, 48, 3887-3890.Balalaie, S.; Arabanian, A. Green Chem 2000, 2, 274.
47. Mobinikhaledi, A.,;, Foroughifar, N.,;, Fard, M. A. B.,;, Moghanian, H.,;, Ebrahimi, S.,;, Kalhor, M., Synth Commun 2009, 39, 1166.
48. Ko, S. K.,;, Yao, C. F., Tetrahedron 2006, 62, 7293.
49. (a), Evans, C. G.,;, Gestwicki, J. E., Org Lett 2009, 11, 2957;
50. (b), Karade, N. N.,;, Budhewar, V. H.,;, Shinde, S. V.,;, Jadhav, W. N., Lett Org Chem 2007, 4, 16;
51. (c), Kumar, A.,;, Maurya, R. A., Tetrahedron 2007, 63, 1946.
52. (a), Breitenbucher, J. G.,;, Figliozzi, G., Tetrahedron Lett 2000, 41, 4311;
53. (b), Dondoni, A.,;, Massi, A.,;, Minghini, E.,;, Bertolasi, V., Tetrahedron 2004, 60, 2311.
54. (a), Kikuchi, S.,;, Iwai, M.,;, Murayama, H.,;, Fukuzawa, S. I., Tetrahedron Lett 2008, 49, 114;
55. (b), Donelson, J. L.,;, Gibbs, R. A.,;, De, S. K. J., Mol Catal Chem 2006, 256, 309;
56. (c), Wang, L. M.,;, Sheng, J.,;, Zhang, L.,;, Han, J. W.,;, Fan, Z. Y.,;, Tian, H.,;, Qian, C. T., Tetrahedron 2005, 61, 1539.
57. Fairbrother, R. W.,;, Martyn, G., J Clin Pathol 1951, 4, 374.
58. Gould, J. C.,;, Bowie, J. H., J Edinb Med 1952, 59, 178.