Copper(II) triflate-sodium dodecyl sulfate catalyzed preparation of 1,2-diphenyl-2,3-dihydro-4-pyridones in aqueous acidic medium

Synthesis (Germany)

Volumn 44, Issue 14, 2012, Pages 2181-2184

  Lanari, Daniela ^a   Piermatti, Oriana ^a   Pizzo, Ferdinando ^a   Vaccaro, Luigi ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

aqueous medium; aza Diels Alder reaction; copper(II) triflate; Lewis acid; pyridones

Indexed keywords

AQUEOUS MEDIUM; AZA-DIELS-ALDER REACTION; COPPER TRIFLATE; LEWIS ACID; PYRIDONES;

COPPER; OLEFINS; SODIUM;

SODIUM SULFATE;

1 (4 BROMOPHENYL) 2 PHENYL 2,3 DIHDYROPYRIDIN 4(1H) ONE; 1 (4 NITROPHENYL) 2 PHENYL 2,3 DIHDYROPYRIDIN 4(1H) ONE; 1 METHOXY 5 [(4 NITROPHENYL)AMINO] 5 PHENYPENT 1 EN 3 ONE; 1,2 DIPHENYL 2,3 DIHDYROPYRIDIN 4(1H) ONE; 1,2 DIPHENYL 2,3 DIHYDRO 4 PYRIDONE; 2 (2 HYDROXYPHENYL) 1 PHENYL 2,3 DIHDYROPYRIDIN 4(1H) ONE; ALKADIENE; COPPER TRIFLUOROMETHANESULFONIC ACID; DODECYL SULFATE SODIUM; N BENZYLIDENEANILINE; PYRIDONE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; PH MEASUREMENT;

EID: 84863717561     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1291040     Document Type: Article

References (45)

1. Comins DL, Brown JD. Tetrahedron Lett.: 1986; 27 4549
2. Comins DL, Hong H, Salvador JM. J. Org. Chem.: 1991; 56 7197
3. Comins DL, Killpack MO. J. Am. Chem. Soc.: 1992; 114 10972
4. Creighton CJ, Zapf CW, Bu JH, Goodman M. Org. Lett.: 1999; 1 1407
5. Dong D, Bi X, Liu Q, Cong F. Chem. Commun.: 2005; 3580
6. Hoffman RW. Chem. Rev.: 1989; 89 1841
7. Johnson F. Chem. Rev.: 1968; 68 375
8. Comins DL, Dehghani A. Tetrahedron Lett.: 1991; 32 5697
9. Comins DL, Al-Awar RS. J. Org. Chem.: 1992; 57 4098
10. Comins DL, Hong H. J. Am. Chem. Soc.: 1993; 115 8851
11. Comins DL, Hong H. J. Org. Chem.: 1993; 58 5035
12. Comins DL, Radi Benjelloun N. Tetrahedron Lett.: 1994; 35 829
13. Comins DL, Huang S, McArdle CL, Ingalls CL. Org. Lett.: 2001; 3 469
14. Tsukanov SV, Comins DL. Angew. Chem. Int. Ed.: 2011; 50 8626
15. Paradowska J, Stodulski M, Mlynarski J. Angew. Chem. Int. Ed.: 2009; 48 4288
16. Gruttadauria M, Giacalone F, Noto R. Adv. Synth. Catal.: 2009; 351 33
17. Kobayashi S. Pure Appl. Chem.: 2007; 79 235
18. Organic Synthesis in Water. Lindström UM. Blackwell Oxford: 2007
19. Bonollo S, Lanari D, Pizzo F, Vaccaro L. Eur. J. Org. Chem.: 2011; 2587
20. Bonollo S, Lanari D, Pizzo F, Vaccaro L. Org. Lett.: 2011; 13 2150
21. Manabe K, Mori Y, Wakabayashi T, Nagayama S, Kobayashi S. J. Am. Chem. Soc.: 2000; 122 7202
22. Azoulay S, Manabe K, Kobayashi S. Org. Lett.: 2005; 7 4593
23. Ogawa C, Azoulay S, Kobayashi S. Heterocycles: 2005; 66 201
24. Boudou M, Ogawa C, Kobayashi S. Adv. Synth. Catal.: 2006; 348 2585
25. Ogawa C, Wang N, Boudou M, Azoulay S, Manabe K, Kobayashi S. Heterocycles: 2007; 72 589
26. Kobayashi S, Ishitani H. Chem. Rev.: 1999; 99 1069
27. Jorgensen KA. Angew. Chem. Int. Ed.: 2000; 39 3558
28. Laurent-Robert H, Garrigueus B, Dubac J. Synlett: 2000; 1160
29. Buonora J.-C, Olsen OT. Tetrahedron: 2001; 57 6069
30. Collin J, Jaber N, Lannou MI. Tetrahedron Lett.: 2001; 42 7405
31. Yuan Y, Li X, Ding K. Org. Lett.: 2002; 4 3309
32. Bari LD. A, Guillarme S, Hermitage S, Howard JA. K, Yay D, Pescitelli G, Whiting A, Yufit DS. Synlett: 2004; 708
33. Cheng K, Lin L, Chen S, Feng X. Tetrahedron: 2005; 61 9594
34. Park Y, Park E, Jung H, Lee Y.-J, Jew S.-S, Park H.-G. Tetrahedron: 2011; 67 1166
35. Manabe K, Mori Y, Kagoshima H. Tetrahedron Lett.: 1999; 40 7831
36. Akiyama T, Takaya J, Kagoshima H. Tetrahedron Lett.: 1999; 40 7831
37. Manabe K, Mori Y, Kobayashi S. Tetrahedron: 2001; 57 2537
38. Loncaric C, Manabe K, Kobayashi S. Chem. Commun.: 2003; 574
39. Loncaric C, Manabe K, Kobayashi S. Adv. Synth. Catal.: 2003; 345 475
40. Li C.-J, Chen L. Chem. Soc. Rev.: 2006; 35 68
41. Bonollo S, Fringuelli F, Pizzo F, Vaccaro L. Green Chem.: 2006; 8 960
42. Bonollo S, Fringuelli F, Pizzo F, Vaccaro L. Synlett: 2007; 2683
43. Bonollo S, Fringuelli F, Pizzo F, Vaccaro L. Synlett: 2008; 1574
44. Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L. Org. Lett.: 2005; 7 4411
45. Bonollo S, Fringuelli F, Pizzo F, Vaccaro L. Synlett: 2007; 2683