Organometallic alkylation of 2-chloro-4,6-dimethoxy-1,3,5-triazine: A study

Tetrahedron

Volumn 61, Issue 18, 2005, Pages 4475-4483

  Samaritani, Simona ^a   Signore, Giovanni ^a   Malanga, Corrado ^a   Menicagli, Rita ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

2 Chloro 4,6 dimethoxy 1,3,5 triazine; Coupling reactions; Organometallics; Palladium and nickel catalysts

Indexed keywords

2 (1' PROPENYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (2' METHYL 2' PROPENYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (2' METHYLBUTYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (2' METHYLPROP 1' ENYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (2' METHYLPROPYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (2' PHENYLETHYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (2' PROPENYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (3' FLUOROPHENYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (4' ETHOXYCARBONYLPHENYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (4' METHOXYPHENYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (HEX 1' ENYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 BENZYL 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 ETHYL 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 ISOPROPYL 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 N HEXYL 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 PHENYL 4,6 DIMETHOXY 1,3,5 TRIAZINE; HALIDE; NICKEL; ORGANOMETALLIC COMPOUND; ORGANOTIN COMPOUND; PALLADIUM; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CROSS COUPLING REACTION; DRUG SYNTHESIS; GRIGNARD REACTION; PRIORITY JOURNAL;

EID: 17044423001     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.085     Document Type: Article

References (53)

1. (a) Kukla, M. J.; Ludovici, D. W.; Janssen, P. A. J.; Heeres, J.; Moereels, H. E. L. Eur. Pat. Appl. EP 834 507 A1, 1998.
2. A.F. Pozharskii, A.T. Soldatenkov, and A.R. Katritzky Heterocycles in Life and Society 1977 Wiley Chichester
3. (c) Vaglini, F.; Samaritani, S.; Cavalletti, M.; Menicagli, R.; Salvadori, P. Cost Action D13 Workshop: New Molecules Towards Human Health Care, Firenze 17-20 Aprile 2002, Atti P21.
4. (d) Samaritani, S., Cavalletti, M., Dioguardi, A., Vaglini, F., Menicagli, R., Salvadori, P. 3rd Italian-French meeting on Organic Chemistry: Organic Chemistry Towards Interfaces, Pisa 20-23 Novembre 2002, Atti P50.
5. R. Menicagli, S. Samaritani, G. Signore, F. Vaglini, and L. Dalla Via J. Med. Chem. 47 2004 4649 4652
6. D. Janietz, and M. Bauer Synthesis 1993 33 34
7. M. Fujita, H. Oka, and K. Ogura Tetrahedron Lett. 36 1995 5247 5250
8. R. Faust, and B. Göbelt Tetrahedron Lett. 38 1997 8017 8020
9. G. Cooke, H.A. de Cremiers, V.M. Rotello, B. Tarbit, and P.E. Vanderstraeten Tetrahedron 57 2001 2787 2789
10. A. Fürstner, A. Leitner, M. Méndez, and H. Krause J. Am. Chem. Soc. 124 2002 13856 13863
11. R. Menicagli, S. Samaritani, and S. Gori Tetrahedron Lett. 40 1999 8419 8422
12. S. Samaritani, and R. Menicagli Tetrahedron 58 2002 1381 1386
13. V. Farina, V. Krishnamurthy, and W.J. Scott The Stille Reaction in Organic Reactions Vol. 50 1997 Wiley New York and references therein
14. J. Solberg, and K. Undheim Acta Chem. Scand., Ser. B B41 1987 712 716
15. V. Nair, and A.G. Lyons Tetrahedron 45 1989 3653 3662
16. J.W. Tilley, R. Sarabu, R. Wagner, and K. Mulkerins J. Org. Chem. 55 1990 906 910
17. V. Farina, and B. Krishnan J. Am. Chem. Soc. 113 1991 9585 9595
18. A.M. Echavarren, N. Tamayo, and M.C. Paredes Tetrahedron Lett. 34 1993 4713 4716
19. R.M. Moriarty, W.R. Epa, and A.K. Awasthi Tetrahedron Lett. 31 1990 5877 5880
20. K. Undheim, and T. Benneche Organometallics in Coupling Reactions in π-Deficient Azaheterocycles Adv. Heterocycl. Chem. 62 1995 305 418
21. H.C. Brown, T. Hamaoka, and N. Ravindran J. Am. Chem. Soc. 95 1973 5786 5788
22. G. Zweifel, and C.C. Whitney J. Am. Chem. Soc. 89 1967 2753 2754
23. H.C. Brown Hydroboration 1962 Benjamin New York and references therein
24. G. Zweifel, and J.A. Miller Syntheses Using Alkyne-derived Alkenyl- and Alkynylaluminum Compounds in Organic Reactions Vol. 32 1984 Wiley New York and references therein
25. E.F. Magoon, and L.H. Slaugh Tetrahedron 23 1967 4509 4515
26. B.L. Groh Tetrahedron Lett. 32 1991 7647 7650
27. H. Shinokubo, and K. Oshima Catalysis Surveys from Asia 7 2003 39 46
28. H. Shinokubo, and K. Oshima Eur. J. Org. Chem. 2004 2081 2091
29. S. Baba, and E. Negishi J. Am. Chem. Soc. 98 1976 6729 6731
30. E. Negishi, N. Okukado, A.O. King, D.E. Van Horn, and B.I. Spiegel J. Am. Chem. Soc. 100 1978 2254 2256
31. T. Hayashi, Y. Katsuro, Y. Okamoto, and M. Kumada Tetrahedron Lett. 22 1981 4449 4452
32. E. Negishi, and H.C. Brown Handbook of Organopalladium Chemistry for Organic Synthesis 2002 Wiley New York and references therein
33. T. Mole, and E.A. Jeffery Organoaluminium Compounds 1972 Elsevier New York
34. M.D. Fryzuk, B.R. Lloyd, G.K. Cletsmith, and S.J. Retting J. Am. Chem. Soc. 116 1994 3804 3812
35. 13C NMR: 13.5, 20.5, 40.3, 54.8, 172.2, 183.1.
36. J.S. Filippo Jr., J. Silbermann, and P.J. Fagan J. Am. Chem. Soc. 100 1978 4834 4842
37. H. Azizian, C. Eaborn, and A. Pidcock J. Organometal. Chem. 215 1981 49 58
38. B.M. Trost, and J.W. Herndon J. Am. Chem. Soc. 106 1984 6835 6837
39. E. Erdik Organozinc Reagents in Organic Synthesis 1996 CRC
40. D.D. Perrin, W.L.F. Armarego, and D.R. Perrin Purification of Laboratory Chemicals 1983 Pergamon New York
41. J.S. Cronin, F.O. Ginah, A.R. Murray, and J.D. Copp Synth. Commun. 26 1996 3491 3494
42. B.J. Wakefield Organomagnesium Methods in Organic Synthesis 1995 Academic New York
43. D. Masilamani, E.H. Manahan, J. Vitrone, and M.M. Rogic J. Org. Chem. 48 1983 4918 4931
44. L. Lardicci Gazz. Chim. It. 91 1961 458 466
45. J.J. Eisch, and M.W. Foxton J. Org. Chem. 36 1971 3520 3526
46. A.G. Davies Tin in Comprehensive Organometallic Chemistry 1982 Pergamon New York
47. F.R. Jensen J. Am. Chem. Soc. 79 1957 1226 1231
48. E. Negishi, N. Okukado, S.F. Lovich, and F.T. Luo J. Org. Chem. 49 1984 2629 2632
49. D.R. Coulson Inorganic Synthesis 28 1990 107 109
50. H. Itatani, and J.C. Bailas J. Am. Oil Chem. Soc. 44 1967 147 151
51. G.R. Van Hecke, and W.D. Horrocks Inorg. Chem. 5 1966 1968 1974
52. G.A. Russell, and L.H. Lourdes J. Org. Chem. 1985 1037 1040
53. Y. Ueno Tetrahedron Lett. 21 1980 1767 1770