A 1,3-amino group migration route to form acrylamidines

Chemical Communications

Volumn 50, Issue 3, 2014, Pages 323-325

  Chauhan, Dinesh Pratapsinh ^a   Varma, Sreejith Jayasree ^a   Vijeta, Arjun ^a   Banerjee, Pallavi ^a   Talukdar, Pinaki ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 AMINO GROUP; ACRYLAMIDINE DERIVATIVE; AMIDINE; AMINE; AZIDE; COPPER; IMINE; KETENIMINE; NUCLEOPHILE; PROPARGYLAMINE; TOSYLAZIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

AMIDINES; CATALYSIS; CLICK CHEMISTRY; COPPER; PARGYLINE; PROPYLAMINES;

EID: 84889258120     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc47182a     Document Type: Article

References (33)

1. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed., 2001, 40, 2004.
2. N. J. Agard, J. A. Prescher, C. R. Bertozzi, J. Am. Chem. Soc., 2004, 126, 15046.
3. J. C. Jewett, C. R. Bertozzi, Chem. Soc. Rev., 2010, 39, 1272.
4. W. G. Lewis, L. G. Green, F. Grynszpan, Z. Radic, P. R. Carlier, P. Taylor, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed., 2002, 41, 1053.
5. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., Int. Ed., 2002, 41, 2596.
6. J. Lahann, Click Chemistry for Biotechnology and Materials Science, John Wiely & Sons, Chichester, West Sussex, 2009
7. C. Le Droumaguet, C. Wang, Q. Wang, Chem. Soc. Rev., 2010, 39, 1233.
8. R. Breinbauer, M. Koehn, ChemBioChem, 2003, 4, 1147.
9. A. H. El-Sagheer, T. Brown, Chem. Soc. Rev., 2010, 39, 1388.
10. P. Wu, A. K. Feldman, A. K. Nugent, C. J. Hawker, A. Scheel, B. Voit, J. Pyun, J. M. J. Frechet, K. B. Sharpless, V. V. Fokin, Angew. Chem., Int. Ed., 2004, 43, 3928.
11. H. C. Kolb, K. B. Sharpless, Drug Discovery Today, 2003, 8, 1128.
12. J. M. Holub, K. Kirshenbaum, Chem. Soc. Rev., 2010, 39, 1325.
13. E. J. Yoo, M. Ahlquist, S. H. Kim, I. Bae, V. V. Fokin, K. B. Sharpless, S. Chang, Angew. Chem., Int. Ed., 2007, 46, 1730.
14. I. Bae, H. Han, S. Chang, J. Am. Chem. Soc., 2005, 127, 2038.
15. E. J. Yoo, M. Ahlquist, I. Bae, K. B. Sharpless, V. V. Fokin, S. Chang, J. Org. Chem., 2008, 73, 5520.
16. S. H. Kim, D. Y. Jung, S. Chang, J. Org. Chem., 2007, 72, 9769.
17. E. J. Yoo, S. Chang, Curr. Org. Chem., 2009, 13, 1766.
18. S. H. Cho, E. J. Yoo, I. Bae, S. Chang, J. Am. Chem. Soc., 2005, 127, 16046.
19. E. J. Yoo, I. Bae, S. H. Cho, H. Han, S. Chang, Org. Lett., 2006, 8, 1347.
20. S. H. Cho, S. Chang, Angew. Chem., Int. Ed., 2008, 47, 2836.
21. J. Wang, J.-J. Wang, Y.-X. Zhu, P. Lu, Y.-G. Wang, Chem. Commun., 2011, 47, 3275.
22. J. Kim, S. Y. Lee, J. Lee, Y. Do, S. Chang, J. Org. Chem., 2008, 73, 9454.
23. E. J. Yoo, S. H. Park, S. H. Lee, S. Chang, Org. Lett., 2009, 11, 1155.
24. W. Song, W. Lu, J. Wang, P. Lu, Y. Wang, J. Org. Chem., 2010, 75, 3481.
25. K. K. R. Tetala, R. J. Whitby, M. E. Light, M. B. Hurtshouse, Tetrahedron Lett., 2004, 45, 6991.
26. N. Shindoh, K. Kitaura, Y. Takemoto, K. Takasu, J. Am. Chem. Soc., 2011, 133, 8470.
27. X. Yan, J. Liao, Y. Lu, J. Liu, Y. Zeng, Q. Cai, Org. Lett., 2013, 15, 2478.
28. N. Shindoh, Y. Takemoto, K. Takasu, Chem. Eur. J., 2009, 15, 7026.
29. G. V. Boyd, in, The Chemistry of Amidines and Imidates, ed. S. Patai and Z. Rappoport, Wiley, New York, 1991, ch. 8, vol. 2
30. B. Ojo, P. G. Dunbar, G. J. Durant, P. I. Nagy, J. J. Huzl III, S. Periasamy, D. O. Ngur, A. A. El-Assadi, W. P. Hoss, W. S. Messer Jr., Bioorg. Med. Chem., 1996, 4, 1605.
31. C. Thominiaux, B. de Bruin, Y. Bramoulle, F. Hinnen, S. Demphel, H. Valette, M. Bottlaender, L. Besret, M. Kassiou, F. Dolle, Appl. Radiat. Isot., 2006, 64, 348.
32. T. R. M. Rauws, B. U. W. Maes, Chem. Soc. Rev., 2012, 41, 2463.
33. C. Wentrup, V. V. R. Rao, W. Frank, B. E. Fulloon, D. W. J. Moloney, T. Mosandl, J. Org. Chem., 1999, 64, 3608.