Selective reduction of nitroarenes by a Hantzsch 1,4-dihydropyridine: A facile and efficient approach to substituted quinolines

Synthesis

Volumn , Issue 13, 2011, Pages 2066-2072

  Xing, Rui Guang ^a   Li, Ya Nan ^a   Liu, Qiang ^a,b   Han, Yi Feng ^b   Wei, Xia ^a   Li, Jing ^a   Zhou, Bo ^a  

^a LANZHOU UNIVERSITY   (China)

^b ZHEJIANG SCI TECH UNIVERSITY   (China)

Author keywords

biomimetic reducing agent; Hantzsch ester; quinolines; reductive cyclization

Indexed keywords

1 ,4-DIHYDROPYRIDINE; HANTZSCH ESTER; NITROARENES; QUINOLINES; REDUCTIVE CYCLIZATION; SELECTIVE REDUCTION;

BIOMIMETICS; CYCLIZATION; ESTERIFICATION; ESTERS; PYRIDINE;

SELECTIVE CATALYTIC REDUCTION;

(2 METHYLQUINOLIN 3 YL)(PHENYL)METHANONE; 1 (2 METHYLQUINOLIN 3 YL)ETHANONE; 1,4 DIHYDROPYRIDINE; 2 (2 METHOXYPHENYL)QUINOLINE; 2 (2 NITROBENZYLIDENE) 1,3 DICARBONYL; 2 (2 NITROBENZYLIDENE)CYCLOPENTANONE; 2 (2 TOLYL)QUINOLINE; 2 (3 METHOXYPHENYL)QUINOLINE; 2 (4 BROMOPHENYL)QUINOLINE; 2 (4 CHLOROPHENYL)QUINOLINE; 2 (4 METHOXYPHENYL)QUINOLINE; 2 (4 TOLYL)QUINOLINE; 2 (NAPHTHALEN 1 YL)QUINOLINE; 2 (PYRIDIN 3 YL)QUINOLINE; 2 [4 (TRIFLUOROMETHYL)PHENYL]QUINOLINE; 2 NITROCINNAMOYL; 2 PHENYLQUINOLINE; 2,3 DIHYDRO 1H CYCLOPENTA[B]QUINOLINE; AROMATIC NITRO COMPOUND; CARBON; ETHYL 2 METHYLQUINOLINE 3 CARBOXYLATE; ETHYL 2 OXO 1,2 DIHYDROQUINOLINE 3 CARBOXYLATE; PALLADIUM; PHENYL(2 PHENYLQUINOLIN 3 YL)METHANONE; QUINALDINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HANTZSCH REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 80955180606     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260609     Document Type: Article

References (45)

1. Zhang X, Campo M A., Yao T, Larock R C., Org. Lett. 2005 7 763; and references cited therein
2. Scott T L., Soderberg B C. G., Tetrahedron 2003 59 6323
3. Cenini S, Bettettini E, Fedele M, Tollari S, [nl]J. Mol. Catal. A: Chem. 1996 111 37
4. Akazome M, Kondo T, Watanabe Y, J. Org. Chem. 1994 59 3375
5. Ma Y, Zhang Y, J. Chem. Res., Synop. 2001 108
6. Shi D, Rong L, Wang J, Zhuang Q, Wang X, Tu S, Hu H, J. Chem. Res., Synop. 2003 342
7. Wang X, Zhang Y, Synth. Commun. 2002 32 3627
8. Han R, Chen S, Lee S J., Qi F, Wu X, Kim B H., Heterocycles 2006 68 1675
9. Jiang H, Qi F, Wu X, Han R, Huaxue Shiji 2008 30 295
10. Barros A I. N. A., Silva A M. S., Tetrahedron Lett. 2003 44 5893
11. Barros A I. N. A., Dias A F. R., Silva A M. S., Monatsh. Chem. 2007 138 585
12. Parvatkar P T., Parameswaran P S., Tilve S G., Tetrahedron Lett. 2007 48 7870
13. Baik W, Kim D I., Lee H J., Chung W J., Kim B H., Lee S W., Tetrahedron Lett. 1997 38 4579
14. Yamane Y, Liu X, Hamasaki A, Ishida T, Haruta M, Yokoyama T, Tokunaga M, Org. Lett. 2009 11 5162
15. Shimizu K, Miyamoto Y, Kawasaki T, Tanji T, Tai Y, Satsuma A, J. Phys. Chem. C 2009 113 17803
16. Liang M, Wang X, Liu H, Liu H, Wang Y, J. Catal. 2008 255 335
17. Zhao S, Liang H, Zhou Y, Catal. Commun. 2007 8 1305; and references cited therein
18. Mitsumori S, Tsuri T, Honma T, Hiramatsu Y, Okada T, Hashizume H, Inagaki M, Arimura A, Yasui K, Asanuma F, Kishino J, Ohtani M, J. Med. Chem. 2003 46 2436
19. Bellamy F D., Ou K, Tetrahedron Lett. 1984 25 839
20. Naffziger M R., Ashburn B O., Perkins J R., Carter R G., J. Org. Chem. 2007 72 9857
21. Rahaim R J., Maleczka R E., Org. Lett. 2005 7 5087
22. Rahaim R J., Maleczka R E., Synthesis 2006 3316
23. Noronha R G., Romao C C., Fernandes A C., J. Org. Chem. 2009 74 6960; and references cited therein
24. Saha A, Ranu B, J. Org. Chem. 2008 73 6867
25. Fukuzumi S, Chiba M, Tanaka T, J. Chem. Soc., Chem. Commun. 1989 941
26. Fukuzumi S, Tokuda Y, Bull. Chem. Soc. Jpn. 1992 65 831
27. Shen X X., Liu Q, Xing R G., Zhou B, Catal. Lett. 2008 126 361
28. Liu Q, Li J, Shen X X., Xing R G., Yang J, Liu Z G., Zhou B, Tetrahedron Lett. 2009 50 1026
29. Meng Q Y., Liu Q, Li J, Xing R G., Shen X X., Zhou B, Synlett 2009 3283
30. Zhao Y K., Liu Q, Li J, Liu Z G., Zhou B, Synlett 2010 1870
31. Xing R G., Li Y N., Liu Q, Meng Q Y., Li J, Shen X X., Liu Z G., Zhou B, Yao X J., Liu Z L., Eur. J. Org. Chem. 2010 6627
32. Yang J W., Fonseca M T. H., List B, Angew. Chem. Int. Ed. 2004 43 6660
33. Yang J W., Fonseca M T. H., Vignola N, List B, Angew. Chem. Int. Ed. 2005 44 108
34. Ouellet S G., Tuttle J B., MacMillan D W. C., J. Am. Chem. Soc. 2005 127 32
35. Mayer S, List B, Angew. Chem. Int. Ed. 2006 45 4193
36. Tuttle J B., Ouellet S G., MacMillan D W. C., J. Am. Chem. Soc. 2006 128 12662
37. Martin N J. A., List B, J. Am. Chem. Soc. 2006 128 13368
38. Martin N J. A., Ozores L, List B, J. Am. Chem. Soc. 2007 129 8976
39. Ouellet S G., Walji A M., Macmillan D W. C., Acc. Chem. Res. 2007 40 1327
40. Rueping M, Antonchick A P., Theissmann T, Angew. Chem. Int. Ed. 2006 45 3683
41. Liu Z, Han B, Liu Q, Zhang W, Yang L, Liu Z L., Yu W, Synlett 2005 1579
42. Liu Z, Liu Q, Zhang W, Mu R, Yang L, Liu Z L., Yu W, Synthesis 2006 771
43. Garden S J., Guimaraes C R. W., Correa M B., Oliveira C A. F., Pinto A C., Alencastro R B., J. Org. Chem. 2003 68 8815
44. Austin M, Egan O J., Tully R, Pratt A C., Org. Biomol. Chem. 2007 5 3778
45. Smith C D., Rosocha G, Mui L, Batey R A., J. Org. Chem. 2010 75 4716