Nucleophilic addition to 2,3-pyridyne and synthesis of benzonaphthyridinones

Tetrahedron

Volumn 68, Issue 13, 2012, Pages 2819-2826

  Fang, Yuesi ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

2,3 Pyridyne; Amination; Annulation; Benzonaphthyridinone; Heterocycle

Indexed keywords

2,3 PYRIDYNE; AMINE; ANTHRANILIC ACID; BENZONAPHTHYRIDINONE DERIVATIVE; HETEROCYCLIC COMPOUND; NAPHTHYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; AMINATION; ARTICLE; NUCLEOPHILICITY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 84857913855     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.02.002     Document Type: Article

References (51)

1. K. Mink, and F. Bracher Arch. Pharm. (Weinheim, Ger.) 340 2007 429
2. Koch, M.; Tillequin, F.; Michel, S.; Hickman, J.; Pierre, A.; Leonce, S.; Pfeiffer, B.; Renard, P.; U.S. Patent Appl. Publ. 24, 2005.
3. H. Misbahi, P. Brouant, A. Hever, A.M. Molnar, K. Wolfard, G. Spengler, H. Mefetah, J. Molnar, and J. Barbe Anticancer Res. 22 2002 2097
4. F. Trécourt, F. Marsais, T. Güngör, and G. Quéguiner J. Chem. Soc., Perkin Trans. 1 1990 2409
5. W.A. Denny, G.J. Atwell, and B.F. Cain J. Med. Chem. 20 1977 1242
6. C. Afloroaei, M. Vlassa, A. Becze, P. Brouant, and J. Barbe Heterocycl. Commun. 5 1999 249
7. M. Manoj, and K.J.R. Prasad Synth. Commun. 40 2010 3290
8. M. Manoj, and K.J.R. Prasad J. Chem. Res. 2009 720
9. W. Sander Acc. Chem. Res. 32 1999 669
10. G. Wittig Naturwissenschaften 30 1942 696
11. J.D. Roberts, D.A. Semenow, H.E. Simmons Jr., and L.A. Carlsmith J. Am. Chem. Soc. 78 1956 601
12. Y. Himeshima, T. Sonoda, and H. Kobayashi Chem. Lett. 1983 1211
13. Y. Fang, C. Wu, R.C. Larock, and F. Shi J. Org. Chem. 76 2011 8840
14. D.C. Rogness, and R.C. Larock J. Org. Chem. 76 2011 4980
15. A. Kivrak, and R.C. Larock J. Org. Chem. 75 2010 7381
16. A.V. Dubrovskiy, and R.C. Larock Org. Lett. 12 2010 3117
17. C. Wu, Y. Fang, R.C. Larock, and F. Shi Org. Lett. 12 2010 2234
18. D.C. Rogness, and R.C. Larock J. Org. Chem. 75 2010 2289
19. Z. Liu, and R.C. Larock Org. Lett. 5 2003 4673
20. Z. Liu, and R.C. Larock Org. Lett. 6 2004 99
21. Z. Liu, and R.C. Larock J. Org. Chem. 71 2006 3198
22. J. Zhao, and R.C. Larock Org. Lett. 7 2005 4273
23. J. Zhao, and R.C. Larock J. Org. Chem. 72 2007 583
24. T. Kauffmann Angew. Chem., Int. Ed. Engl. 4 1965 543
25. W. Adam, A. Grimison, and R. Hoffmann J. Am. Chem. Soc. 91 1969 2590
26. H. Pellissier, and M. Santelli Tetrahedron 59 2003 701
27. S.M. Bronner, A.E. Goetz, and N.K. Garg Synlett 2011 2559
28. A.N. Garr, D. Luo, N. Brown, C.J. Cramer, K.R. Buszek, and D. VanderVelde Org. Lett. 12 2010 96
29. M. Díaz, A. Cobas, E. Guitián, and L. Castedo Eur. J. Org. Chem. 2001 4543
30. H.J. den Hertog, and H.C. van der Plas A.R. Katritzky, Advances in Heterocyclic Chemistry Vol. 4 1965 Academic New York, NY 121 198
31. M.G. Reinecke Tetrahedron 38 1982 427
32. H.C. van der Plas, and F. Roeterdink S. Patai, Z. Rappoport, The Chemistry of Triple-Bonded Functional Groups Supplement C 1983 John Wiley & Sons Chichester, UK 421 511
33. H. Hart S. Patai, The Chemistry of Triple-bonded Functional Groups Supplement C2 Vol. 2 1994 John Wiley & Sons Chichester, UK 1017 1134
34. S.J. Connon, and A.F. Hegarty Tetrahedron Lett. 42 2001 735
35. S.J. Connon, and A.F. Hegarty Eur. J. Org. Chem. 2004 3477
36. G.W.J. Fleet, and I. Fleming J. Chem. Soc. C 1969 1758
37. J. Kurita, N. Kakusawa, S. Yasuike, and T. Tsuchiya Heterocycles 31 1990 1937
38. M. Mallet, G. Queguiner, and P. Pastour Comp. Rend. 274 1972 719
39. J.D. Cook, and B.J. Wakefield J. Chem. Soc. C 1969 1973
40. R.J. Martens, and H.J. den Hertog Tetrahedron Lett. 1962 643
41. R.J. Martens, and H.J. den Hertog Recl. Trav. Chim. Pays-Bas 83 1964 621
42. F. Effenberger, and W. Daub Chem. Ber. 124 1991 2119
43. M.A. Walters, and J.J. Shay Synth. Commun. 27 1997 3573
44. G.W.J. Fleet, and I. Fleming J. Chem. Soc. C 1971 3948
45. A.A. Cant, G.H.V. Bertrand, J.L. Henderson, L. Roberts, and M.F. Greaney Angew. Chem., Int. Ed. 48 2009 5199
46. L. Radom, R. Nobes, D. Underwood, and W. Li Pure Appl. Chem. 58 1986 75
47. R. Liu, D.R. Tate, J.A. Clark, P.R. Moody, A.S. Van Buren, and J.A. Krauser J. Phys. Chem. 100 1996 3430
48. N. Mariet, M. Ibrahim-Ouali, J. Parrain, and M. Santelli J. Mol. Struct. 679 2004 53
49. N. Marion, E.C. Ecarnot, O. Navarro, D. Amoroso, A. Bell, and S.P. Nolan J. Org. Chem. 71 2006 3816
50. J. Yang, Y. Lin, Y. Lin, and F. Liao J. Org. Chem. 69 2004 3517
51. J. Li, C. Jin, and W. Su Heterocycles 81 2010 2555