Synthesis of N,N-dialkylaminobenzonitriles and halo-(N,N-dialkyl) benzamidines by reaction of halobenzonitriles with lithium amides

Tetrahedron

Volumn 67, Issue 36, 2011, Pages 6944-6952

  Vitale, Paola ^a   Di Nunno, Leonardo ^a   Scilimati, Antonio ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Benzyne mechanism; Lithium amides; N,N Dialkylaminobenzonitriles; N,N Dialkylbenzamidines; Thermodynamic and kinetic control

Indexed keywords

4 CHLOROBENZONITRILE; AMIDE; BENZAMIDINE DERIVATIVE; BENZONITRILE; FLUORESCENT DYE; LITHIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MASS SPECTROMETRY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE; THERMODYNAMICS;

EID: 80051549323     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.06.066     Document Type: Article

References (24)

1. Y.C. Zhu, H. Liu, F. Li, Q. Ruan, H. Wang, M. Fujiwara, L. Wang, and G.Q. Lu J. Am. Chem. Soc. 132 2010 1450 1451
2. M. Braun, C. Root, F.J. Lederer, T.E. Schrader, W. Zinth, C. Korff Schmising, M. Bargheer, T. Elsaesser, and M. Woerner Appl. Phys. A: Mater. Sci. Process. 96 2009 107 115
3. M. Braun, C. Root, T.E. Schrader, P. Gilch, W. Zinth, M. Bargheer, S.C. von Korff, M. Kiel, N. Zhavoronkov, M. Woerner, and T. Elsaesser A.M. Weiner, R.J. Dwayne Miller, Ultrafast Phenomena XV Springer Series in Chem. Physics Vol. 88 2006 Springer Berlin 725 727
4. S. Techert, and K.A. Zachariasse J. Am. Chem. Soc. 126 2004 5593 5600
5. W.M. Kwok, C. Ma, D. Phillips, P. Matousek, A.W. Parker, and M. Towrie J. Phys. Chem. A 104 2000 4188 4197
6. S.I. Druzhinin, N.P. Ernsting, S.A. Kovalenko, L. Pérez Lustres, T. Senyushkina, and K.A. Zachariasse J. Phys. Chem. A 110 2006 2955 2969
7. S. Urgaonkar, and J.G.A. Verkade J. Org. Chem. 69 2004 9135 9142
8. L. Di Nunno, P. Vitale, and A. Scilimati Tetrahedron 64 2008 11198 11204
9. L. Di Nunno, P. Vitale, A. Scilimati, L. Simone, and F. Capitelli Tetrahedron 63 2007 12388 12395
10. M. Lysén, H.M. Hansen, M. Begtrup, and J.L. Kristensen J. Org. Chem. 71 2006 2518 2520
11. M.B. Smith, and J. March March's Advanced Organic Chemistry: Reactions, Mechanisms and Structure 6th ed. 2007 John Hoboken, N.Y Chapter 13, p 861
12. A. Ramirez, J. Candler, C.G. Bashore, M.C. Wirtz, J.W. Coe, and D.B. Collum J. Am. Chem. Soc. 126 2004 14700 14701
13. M.B. Smith, and J. March March's Advanced Organic Chemistry: Reactions, Mechanisms and Structure 6th ed. 2007 John Hoboken, N.Y Chapter 13, p 859
14. G.R. Brown, A.J. Foubister, and P.D. Ratcliffe Tetrahedron Lett. 401 1999 1219 1222
15. G. Wittig, and J. Heyn Justus Liebigs Ann. Chem. 756 1972 1 13
16. J. Hirano, H. Miyata, K. Hamase, and K. Zaitsu Luminescence 23 2008 350 355
17. M. Cortes-Salva, C. Garvin, and J.C. Antilla J. Org. Chem. 76 2011 1456 1459
18. Jpeij, E. G.; Windmuller, P. J. H.; Arts, H. J.; Van der Burgt, F.; van Doremaele, G. H. J.; Zuideveld, M. A.; WO/2005/090418.
19. E. Raczynska, and J. Oszczapowicz Tetrahedron 41 1985 5175 5179
20. M.E. Kort, I. Drizin, R.J. Gregg, M.J.C. Scanio, L. Shi, M.F. Gross, R.N. Atkinson, M. Johnson, G.J. Pacofsky, J.B. Thomas, W.A. Carroll, M.J. Krambis, D. Liu, C.-C. Shieh, X. Zhang, G. Hernandez, J.P. Mikusa, C. Zhong, S. Joshi, P. Honore, R. Roeloffs, K.C. Marsh, B.P. Murray, J. Liu, S. Werness, C.R. Faltynek, D.S. Krafte, M.F. Jarvis, M.L. Chapman, and B.E. Marron J. Med. Chem. 51 2008 407 416
21. P. Zhang, L. Bao, J. Fan, Z.J. Jia, U. Sinha, P.W. Wong, G. Park, A. Hutchaleelaha, R.M. Scarborough, and B.Y. Zhu Bioorg. Med. Chem. Lett. 19 2009 2186 2189
22. J. Suffert J. Org. Chem. 54 1989 509 510
23. A. Demeter, S. Druzhinin, M. George, E. Haselbach, J.-L. Roulin, and K.A. Zachariasse Chem. Phys. Lett. 323 2000 351 360
24. V. del Amo, S.R. Dubbaka, A. Krasovskiy, and P. Knochel Angew. Chem., Int. Ed. 45 2006 7838 7842