Organic Letters
Letter
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the corresponding bistriazoles and, more importantly, to 4-
imino-3,4-dihydroquinazolin-2(1H)-ones and cyanophenylur-
ea derivatives through simple treatment with nucleophilic
amines was presented. In due course, we will report the
synthesis and reactivity of geminal diazides derived from other
heterocycles to further expand the knowledge on the
fascinating chemistry of geminal diazides.25
̀
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ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
Experimental and spectral details for all new compounds
Accession Codes
(8) (a) Chen, W.-T.; Wei, W.-T. Asian J. Org. Chem. 2018, 7, 1429.
(b) Wei, W.-T.; Zhu, W.-M.; Ying, W.-W.; Wang, Y.-N.; Bao, W.-H.;
Gao, L.-H.; Luo, Y.-J.; Liang, H. Adv. Synth. Catal. 2017, 359, 3551.
(c) Ying, W.-W.; Zhu, W.-M.; Gao, Z.; Liang, H.; Wei, W.-T. Synlett
2018, 29, 663. (d) Zhu, W.-M.; Bao, W.-H.; Ying, W.-W.; Chen, W.-
T.; Huang, Y.-L.; Ge, G.-P.; Chen, G.-P.; Wei, W.-T. Asian J. Org.
Chem. 2018, 7, 337. (e) Wei, W.-T.; Zhu, W.-M.; Shao, Q.; Bao, W.-
H.; Chen, W.-T.; Chen, G.-P.; Luo, Y.-J.; Liang, H. ACS Sustainable
Chem. Eng. 2018, 6, 8029.
(9) (a) Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104.
(b) Akita, M.; Seto, H.; Aoyama, R.; Kimura, J.; Kobayashi, K.
Molecules 2012, 17, 13879. (c) Bergman, J.; Arewang, C.-J.; Svensson,
P. H. J. Org. Chem. 2014, 79, 9065.
crystallographic data for this paper. These data can be obtained
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
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Corresponding Author
ORCID
(10) (a) Harschneck, T.; Hummel, S.; Kirsch, S. F.; Klahn, P. Chem.
- Eur. J. 2012, 18, 1187. (b) Klahn, P.; Erhardt, H.; Kotthaus, A.;
Kirsch, S. F. Angew. Chem., Int. Ed. 2014, 53, 7913. (c) Erhardt, H.;
Present Address
̈
Haring, A. P.; Kotthaus, A.; Roggel, M.; Tong, M. L.; Biallas, P.;
Jubermann, M.; Mohr, F.; Kirsch, S. F. J. Org. Chem. 2015, 80, 12460.
̈
‡
̈
Inorganic Chemistry, Bergische Universitat Wuppertal,
(11) The analogous reactions with 1a and TMSN3 in acetonitrile at
room temperature did not yield the expected diazide 2a, when using
PIDA or I2 as the oxidant.
Gaußstr. 20, 42119 Wuppertal, Germany
Notes
(12) Yin, H.; Wang, T.; Jiao, N. Org. Lett. 2014, 16, 2302.
(13) Chen, W.-T.; Gao, L.-H.; Bao, W.-H.; Wei, W.-T. J. Org. Chem.
2018, 83, 11074.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
(14) (a) Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.;
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Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin,
̈
We thank Dr. Bjorn Beele (BUW) for TGA-DSC measure-
V. V. Angew. Chem., Int. Ed. 2004, 43, 3928. (b) Totobenazara, J.;
Burke, A. J. Tetrahedron Lett. 2015, 56, 2853. (c) Erhardt, H.; Mohr,
F.; Kirsch, S. F. Chem. Commun. 2016, 52, 545.
̈
ments. We also thank Prof. Dr. Roland Gortz (BUW) and
Alexander Schaberg (BUW) for impact sensitivity measure-
ments.
(15) (a) Erhardt, H.; Mohr, F.; Kirsch, S. F. Eur. J. Org. Chem. 2016,
2016, 5629. (b) Erhardt, H.; Kunz, K. A.; Kirsch, S. F. Org. Lett. 2017,
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