Palladium-catalyzed intermolecular domino reaction of gem-dibromoenynes with anilines; A one-pot synthesis of quinolines and quinolinones

Synthesis (Germany)

Volumn 44, Issue 17, 2012, Pages 2754-2762

  Meng, Tianhao ^a   Zhang, Wen Xiong ^b   Zhang, Hui Jun ^b   Liang, Yun ^b   Xi, Zhenfeng ^b  

^a INSTITUTE OF CHEMISTRY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

alkenes; enynes; etherification; quinoline; quinolinone

Indexed keywords

ALKENYL; DOMINO PROCESS; ELECTROPHILIC CYCLIZATION; ENYNES; ETHERIFICATION; INTERMOLECULAR DOMINO REACTIONS; ONE-POT SYNTHESIS; PALLADIUM-CATALYZED; PALLADIUM-CATALYZED AMINATION; QUINOLINE; QUINOLINONE;

ANILINE; BROMINE COMPOUNDS; CATALYSIS; OLEFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

2 TERT BUTOXY 3 BUTYL 4 PENTYL 8 PHENYLQUINOLINE; 2 TERT BUTOXY 3 BUTYL 4 PENTYLQUINOLINE; 2 TERT BUTOXY 3 BUTYL 5,7 DIMETHOXY 4 PENTYLQUINOLINE; 2 TERT BUTOXY 3 BUTYL 5,8 DIMETHOXY 4 PENTYLQUINOLINE; 2 TERT BUTOXY 3 BUTYL 6 FLUORO 4 PENTYLQUINOLINE; 2 TERT BUTOXY 3 BUTYL 6 METHOXY 4 PENTYLQUINOLINE; 2 TERT BUTOXY 3 BUTYL 8 METHOXY 4 PENTYLQUINOLINE; 2 TERT BUTOXY 4 BUTYL 3 PROPYLQUINOLINE; 2 TERT BUTOXY 4 HEPTYL 3 HEXYLQUINOLINE; 3 BUTYL 4 PENTYL 1,9 PHENANTHROLIN 2(1H) ONE; 3 BUTYL 4 PENTYL 8 PHENYLQUINOLIN 2(1H) ONE; 3 BUTYL 4 PENTYLBENZO[H]QUINOLIN 2(1H) ONE; 3 BUTYL 4 PENTYLQUINOLIN 2(1H) ONE; 3 BUTYL 5,7 DIMETHOXY 4 PENTYLQUINOLIN 2(1H) ONE; 3 BUTYL 5,8 DIMETHOXY 4 PENTYLQUINOLIN 2(1H) ONE; 3 BUTYL 6 FLUORO 4 PENTYLQUINOLIN 2(1H) ONE; 3 BUTYL 6 METHOXY 4 PENTYLQUINOLIN 2(1H) ONE; 3 BUTYL 8 ISOPROPYL 4 PENTYLQUINOLIN 2(1H) ONE; 3 BUTYL 8 METHOXY 4 PENTYLQUINOLIN 2(1H) ONE; 4 BUTYL 3 PROPYLQUINOLIN 2(1H) ONE; 4 ETHYL 2,3 DIPHENYLQUINOLINE; 4 HEPTYL 3 HEXYLQUINOLIN 2(1H) ONE; 6 BENZYL 2 TERT BUTOXY 3 BUTYL 4 PENTYLQUINOLINE; 6 BENZYL 3 BUTYL 4 PENTYLQUINOLIN 2(1H) ONE; ANILINE; PALLADIUM; QUINOLINE DERIVATIVE; QUINOLINONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; ETHERIFICATION; MOLECULAR INTERACTION; ONE POT SYNTHESIS; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 84865482903     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316613     Document Type: Article

References (41)

1. For a recent comprehensive review on the synthesis and metal-catalyzed reactions of gem -dihalovinyl systems, see: Chelucci G. Chem. Rev.: 2012; 112 1344
2. Chen W, Zhang Y, Zhang L, Wang M, Wang L. Chem. Commun.: 2011; 47 10476
3. Newman SG, Lautens M. J. Am. Chem. Soc.: 2010; 132 11416
4. Arthuls M, Pontikis R, Florent J.-C. Org. Lett.: 2009; 11 4608
5. Bryan CS, Lautens M. Org. Lett.: 2008; 10 4633
6. Viera TO, Meaney LA, Shi Y.-L, Alper H. Org. Lett.: 2008; 10 4899
7. Fang Y.-Q, Lautens M. J. Org. Chem.: 2008; 73 538
8. Bryan CS, Braunger JA, Lautens M. Angew. Chem. Int. Ed.: 2009; 48 7064
9. Newman SG, Aureggi V, Bryanand CS, Lautens M. Chem. Commun.: 2009; 5236
10. Ye S, Liu J, Wu J. Chem. Commun.: 2012; 48 5028
11. He H.-F, Dong S, Chen Y, Yang Y, Le Y, Bao W. Tetrahedron: 2012; 68 3112
12. He H.-F, Dong S, Chen Y, Yang Y, Le Y, Bao W. Tetrahedron: 2012; 68 3112
13. Wang Z.-J, Yang F, Lv X, Bao W. J. Org. Chem.: 2011; 76 967
14. Qin X.-R, Cong X.-F, Zhao D.-B, You J.-S, Lan J.-B. Chem. Commun.: 2011; 47 5611
15. Wang Z.-J, Yang J.-G, Yang F, Bao W. Org. Lett.: 2010; 12 3034
16. Xu H, Zhang Y, Huang J, Chen W. Org. Lett.: 2010; 12 3704
17. Chai DI, Lautens M. J. Org. Chem.: 2009; 74 3054
18. Sun C, Xu B. J. Org. Chem.: 2008; 73 7361
19. Liang Y, Meng T, Zhang H.-J, Xi Z. Synlett: 2011; 911
20. Coste A, Couty F, Evano G. Org. Lett.: 2009; 11 4454
21. Fukudome Y, Naito H, Hata T, Urabe U. J. Am. Chem. Soc.: 2008; 130 1820
22. Zhang H.-J, Song Z, Wang C, Bruneau C, Xi Z. Tetrahedron Lett.: 2008; 49 624
23. Meng T, Zhang H.-J, Xi Z. Tetrahedron Lett.: 2012; in press; 10.1016/j.tetlet.2012.06.060
24. Theeraladanon C, Arisawa M, Nakagawa M, Nishida A. Tetrahedron: Asymmetry: 2005; 16 827
25. Chen YL, Fang KC, Sheu JY, Hsu SL, Tzeng CC. J. Med. Chem.: 2001; 44 2374
26. Barluenga J, Jiménez-Aquino A, Aznar F, Valdés C. J. Am. Chem. Soc.: 2009; 131 4031
27. Barluenga J, Jiménez-Aquino A, Valdés C, Aznar F. Angew. Chem. Int. Ed.: 2007; 46 1529
28. Surry DS, Buchwald SL. Chem. Sci.: 2011; 2 27
29. Hartwig JF. Acc. Chem. Res.: 2008; 41 1534
30. Godoi B, Schumacher RF, Zeni G. Chem. Rev.: 2011; 111 2937
31. Saito T, Ogawa S, Takei N, Kutsumura N, Otani T. Org. Lett.: 2011; 13 1098
32. Ye S, Gao K, Zhou H, Yang X, Wu J. Chem. Commun.: 2009; 5406
33. Pinto A, Neuville L, Retailleau P, Zhu J. Angew. Chem. Int. Ed.: 2007; 46 3291
34. Wu X, Fors BP, Buchwald SL. Angew. Chem. Int. Ed.: 2011; 50 9943
35. Altman RA, Shafir A, Choi A, Lichtor PA, Buchwald SL. J. Org. Chem.: 2008; 73 284
36. Kataoka N, Shelby Q, Stambuli JP, Hartwig JF. J. Org. Chem.: 2002; 67 5553
37. Parrish CA, Buchwald SL. J. Org. Chem.: 2001; 66 2498
38. Wang Y, Liao Q, Zhao P, Xi C. Adv. Synth. Catal.: 2011; 353 2659
39. Salman GA, Hussain M, Iaroshenko VO, Villinger A, Langer P. Adv. Synth. Catal.: 2011; 353 331
40. Ackermann L, Sandmann R, Kaspar LT. Org. Lett.: 2009; 11 2031
41. Martín R, Rodríguez R, Buchwald SL. Angew. Chem. Int. Ed.: 2006; 45 7079