A convenient synthesis of deuterium labeled amines and nitrogen heterocycles with KOt-Bu/DMSO-d6

Tetrahedron

Volumn 71, Issue 9, 2015, Pages 1425-1430

  Hu, Yu ^a   Liang, Liang ^b   Wei, Wen Tao ^a   Sun, Xiang ^a   Zhang, Xue Jing ^a   Yan, Ming ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b GUANGDONG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Amine; Deuterium; H D exchange reaction; KOt Bu; Radical

Indexed keywords

AMINE; DEUTERIUM; DIMETHYL SULFOXIDE; ETHER DERIVATIVE; FREE RADICAL; METHANE; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL LABELING; ELECTRON; ELECTRON TRANSPORT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 84922753163     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.01.015     Document Type: Article

References (24)

1. J. Atzrodt, V. Derdau, T. Fey, and J. Zimmermann Angew. Chem., Int. Ed. 46 2007 7744
2. Y. Sawama, Y. Monguchi, and H. Sajiki Synlett 2012 959
3. P.H. Allen, M.J. Hickey, L.P. Kingston, and D.J. Wilkinson J. Labelled Compd. Radiopharm. 53 2010 731
4. J. Zhou, and J.F. Hartwig Angew. Chem., Int. Ed. 47 2008 5783
5. S. Ma, G. Villa, P.S. Thuy-Boun, A. Homs, and J.-Q. Yu Angew. Chem., Int. Ed. 53 2014 734
6. W.J.S. Lockley, and D. Hesk J. Labelled Compd. Radiopharm. 53 2010 704
7. E.M. Simmons, and J.F. Hartwig Angew. Chem., Int. Ed. 51 2012 3066
8. Y. Yabe, Y. Sawama, Y. Monguchi, and H. Sajiki Chem. - Eur. J. 19 2013 484
9. T. Maegawa, Y. Fujiwara, Y. Inagaki, H. Esaki, Y. Monguchi, and H. Sajiki Angew. Chem., Int. Ed. 47 2008 5394
10. Y. Fujiwara, H. Iwata, Y. Sawama, Y. Monguchi, and H. Sajiki Chem. Commun. 2010 4977
11. Y.-Y. Chen, X.-J. Zhang, H.-M. Yuan, W.-T. Wei, and M. Yan Chem. Commun. 2013 10974
12. W.-T. Wei, X.-J. Dong, S.-Z. Nie, Y.-Y. Chen, X.-J. Zhang, and M. Yan Org. Lett. 15 2013 6018
13. T.-S. Chen, J. Wolinska-Mocydlaanrdz, and L.C. Leitch J. Labeled Compd. Radiopharm. 6 1970 285
14. Sliwka et al. observed the generation of radical intermediates in the basic DMF and DMSO solution via EPR analysis, but the structures of the radicals are unclear, see: C.L. Opstad, T.B. Melo, H.R. Sliwka, and V. Partali Tetrahedron 65 2009 7616
15. J. Dietrich, C. Hulme, and L.H. Hurley Bioorg. Med. Chem. 18 2010 5738
16. Berman, J. M.; Schmid, M. B.; Mendlein, J. D.; Kaplan, N. WO2004/082586A2
17. Branstrom, A.; Josyula, V. P. V. N.; Arnold, M. A.; Gerasyuto, A. I.; Karp, G.; Wang, J. WO2013/033258A1
18. J. Meneyrol, P. Helissey, C. Tratrat, S. Giorgi-Renault, and H.-P. Husson Synth. Commun. 31 2001 987
19. X. Ling, Y. Xiong, R. Huang, X. Zhang, S. Zhang, and C. Chen J. Org. Chem. 78 2013 5218
20. Augeli-Szsfran, C. E.; Lai, Y.; Sakkab, A. T.; Walker, L. C. WO00/76969A1
21. S.-Y. Zhao, H.-Q. Zhang, D.-Q. Zhang, and Z.-Y. Shao Synth. Commun. 42 2012 128
22. Nikam, S.; Mich, A. A. US006121488A.
23. J.W. Gathirwa, and T. Maki Tetrahedron 68 2012 370
24. C. Ebner, C.A. Müller, C. Markert, and A. Pfaltz J. Am. Chem. Soc. 133 2011 4710