Unprecedented two-step synthesis of symmetrical diarylamines from 2-alkyl-1,3-dinitropropanes

Tetrahedron Letters

Volumn 47, Issue 14, 2006, Pages 2295-2297

  Ballini, Roberto ^a   Barboni, Luciano ^a   Femoni, Cristina ^b   Giarlo, Guido ^a   Palmieri, Alessandro ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

1,3 Dinitropropanes; Aromatization; Diarylamines; One pot synthesis

Indexed keywords

EID: 33644758325     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.027     Document Type: Article

References (39)

1. Y.P. Hong, G.J. Tanoury, H.S. Wilkinson, R.P. Bakale, S.A. Wald, and C.H. Senanayake Tetrahedron Lett. 38 1997 5663 5666
2. Y.P. Hong, C.H. Senanayake, T. Xiang, C.P. Vandenbossche, G.J. Tanoury, R.P. Bakale, and S.A. Wald Tetrahedron Lett. 39 1998 3121 3124
3. F.E. Goodson, and J.F. Hartwig Macromolecules 31 1998 1700 1703
4. J. Louie, and J.F. Hartwig Macromolecules 31 1998 6737 6739
5. E. Bellmann, S. Shaheen, S. Thayumanavan, S. Barlow, R. Grubbs, S. Marder, B. Kippelen, and N. Peyghambarian Chem. Mater. 10 1998 1668 1676
6. S. Thayumanavan, S. Barlow, and S.R. Marder Chem. Mater. 9 1997 3231 3235
7. T. Kanbara, A. Honma, and K. Hasegawa Chem. Lett. 1996 1135 1136
8. T. Kanbara, K. Izumi, Y. Nakadani, T. Narice, and K. Hasegawa Chem. Lett. 1997 1185 1186
9. T. Kanbara, K. Izumi, T. Narice, and K. Hasegawa Polym. J. 30 1998 66 68
10. T. Kanbara, T. Imayasu, and K. Hasegawa Chem. Lett. 1998 709 710
11. T. Kanbara, M. Oshima, and K. Hasegawa J. Polym. Sci. Pol. Chem. 36 1998 2155 2160
12. T. Kanbara, M. Oshima, T. Imayasu, and K. Hasegawa Macromolecules 31 1998 8725 8730
13. R.A. Singer, J.P. Sadighi, and S.L. Buchwald J. Am. Chem. Soc. 120 1998 213 214
14. J.P. Sadighi, R.A. Singer, and S.L. Buchwald J. Am. Chem. Soc. 120 1998 4960 4976
15. N. Spetseris, R.E. Ward, and T.Y. Meyer Macromolecules 31 1998 3158 3161
16. G.E. Greco, A.I. Popa, and R.R. Schrock Organometallics 17 1998 5591 5593
17. J.F. Hartwig Angew. Chem., Int. Ed. 37 1998 2046 2067
18. J. March Advanced Organic Chemistry 3rd ed. 1985 Wiley New York
19. G.W. Gribble, P.D. Lord, J. Skotnicki, S.E. Dietz, J.T. Eaton, and J.L. Johnson J. Am. Chem. Soc. 96 1974 7812 7814
20. P. Marchini, G. Liso, and A. Reho J. Org. Chem. 40 1975 3453 3456
21. C.F. Lane Synthesis 1975 135 146
22. J. Lindley Tetrahedron 40 1984 1433 1456
23. H.L. Aalten, G. van Koten, and D.M. Grove Tetrahedron 45 1989 5565 5578
24. A.J. Paine J. Am. Chem. Soc. 109 1987 1496 1502
25. H. Weingarten J. Org. Chem. 29 1964 977 978
26. RN1 Mechanism Vol. 178 1983 American Chemical Society Washington, DC
27. J.E. Shaw, D.C. Kunerth, and S.B. Swanson J. Org. Chem. 41 1976 732 733
28. A.J. Pearson, J.G. Park, S.H. Yang, and Y.-H. Chuang J. Chem. Soc., Chem. Commun. 1989 1363 1364
29. I.C.F.R. Ferreira, M.-J.R.P. Queiroz, and G. Kirsch Tetrahedron 59 2003 975 981 and references cited therein
30. C.K. Bamfield, and P.F. Gordon Chem. Soc. Rev. 1984 441 488
31. C.K. Bradsher Chem. Rev. 87 1987 1277 1297
32. R.C. Larock Comprehensive Organic Transformations 1st ed. 1989 Wiley-VCH New York Chapter 5, pp 93-103
33. R. Ballini, L. Barboni, and G. Bosica J. Org. Chem. 65 2000 6261 6263
34. R. Ballini, L. Barboni, D. Fiorini, G. Giarlo, and A. Palmieri Chem. Commun. 2005 2633 2634
35. X. Bi, D. Dong, Q. Liu, W. Pan, L. Zhao, and B. Li J. Am. Chem. Soc. 127 2005 4578 4579
36. R. Ballini, G. Bosica, D. Fiorini, and A. Palmieri Synthesis 2004 1938 1940
37. R. Ballini, L. Barboni, D. Fiorini, G. Giarlo, and A. Palmieri Green Chem. 12 2005 828 829
38. Crystallographic data (excluding structure factors) for the structures 3b and 3j have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC-279183 and CCDC-279184, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ]. See also the Supplementary data.
39. J. Dale, and L. Vikersveen Acta Chem. Scand. B 42 1988 354 361