Beilstein J. Org. Chem. 2015, 11, 875–883.
14.Lee, J.; Kim, S. J.; Choi, H.; Kim, Y. H.; Lim, I. T.; Yang, H.; Lee, C. S.;
Kang, H. R.; Ahn, S. K.; Moon, S. K.; Kim, D.-H.; Lee, S.; Choi, N. S.;
Lee, K. J. J. Med. Chem. 2010, 53, 6337–6354.
type mechanism responsible for the formation of the 2-amino-
thiophene. In the study, the thiazole formation from the appro-
priately substituted α-methine nitrile compounds was evaluated,
demonstrating its scope as an effecient way of synthesising
2-subsituted thiazoles from readily available, air stable 1,4-
dithiane-2,5-diol (10) as a precursor for 2-mercaptoacetalde-
hyde.
15.Suzuki, T.; Hisakawa, S.; Itoh, Y.; Suzuki, N.; Takahashi, K.;
Kawahata, M.; Yamaguchi, K.; Nakagawa, H.; Miyata, N.
Bioorg. Med. Chem. Lett. 2007, 17, 4208–4212.
16.Alam, M. S.; Liu, L.; Lee, Y.-E.; Lee, D.-U. Chem. Pharm. Bull. 2011,
Experimental
17.Zwilling, D.; Huang, S.-Y.; Sathyasaikumar, K. V.; Notarangelo, F. M.;
Guidetti, P.; Wu, H.-Q.; Lee, J.; Truong, J.; Andrews-Zwilling, Y.;
Hsieh, E. W.; Louie, J. Y.; Wu, T.; Scearce-Levie, K.; Patrick, C.;
Adame, A.; Giorgini, F.; Moussaoui, S.; Laue, G.; Rassoulpour, A.;
Flik, G.; Huang, Y.; Muchowski, J. M.; Masliah, E.; Schwarcz, R.;
Muchowski, P. J. Cell 2011, 145, 863–874.
Supporting Information
Supporting Information File 1
Experimental and analytical data.
18.Pettit, G. R.; Kamano, Y.; Herald, C. L.; Tuinman, A. A.; Boettner, F. E.;
Kizu, H.; Schmidt, J. M.; Baczynskyj, L.; Tomer, K. B.; Bontems, R. J.
19.Hamada, Y.; Hayashi, K.; Shioiri, T. Tetrahedron Lett. 1991, 32,
20.García-Reynaga, P.; VanNieuwenhze, M. S. Tetrahedron Lett. 2012,
Acknowledgements
We would like to acknowledge the funding and support from
the Royal Society (to IRB), Syngenta (to CJM) and Erasmus
Programme of European Union 2013/14 (to LE), that has
enabled this work to be undertaken.
21.Gewald, K.; Schinke, E.; Böttcher, H. Chem. Ber. 1966, 99, 94–100.
22.Sabnis, R. W. Sulfur Rep. 1994, 16, 1–17.
23.Brown, M. D.; Gillon, D. W.; Meakins, G. D.; Whitham, G. H.
J. Chem. Soc., Perkin Trans. 1 1985, 1623–1626.
References
2. Nguyen, T. B.; Ermolenko, L.; Dean, W. A.; Al-Mourabit, A. Org. Lett.
24.Sadek, K. U.; Mourad, A.-F. E.; Abd-Elhafeez, A. E.; Elnagdi, M. H.
25.Asinger, F.; Fabian, K.; Vossen, H.; Hentschel, K.
Justus Liebigs Ann. Chem. 1975, 410–414.
3. Yang, Z.; Chen, X.; Wang, S.; Liu, J.; Xie, K.; Wang, A.; Tan, Z.
4. Bastug, G.; Eviolitte, C.; Markó, I. E. Org. Lett. 2012, 14, 3502–3505.
26.El Rady, E. A. Synth. Commun. 2006, 36, 37–49.
5. Lingaraju, G. S.; Swaroop, T. R.; Vinayaka, A. C.; Kumar, K. S. S.;
Sadashiva, M. P.; Rangappa, K. S. Synthesis 2012, 44, 1373–1379.
27.Elnagdi, M. H.; Khalifa, M. A. E.; Ibraheim, M. K. A.;
Elmoghayar, M. R. H. J. Heterocycl. Chem. 1981, 18, 877–879.
6. Roger, J.; Požgan, F.; Doucet, H. J. Org. Chem. 2009, 74, 1179–1186.
28.Elagamey, A. G. A.; El Taweel, F. A.; Amer, F. A.; Zoorob, H. H.
29.Ma, L.; Yuan, L.; Xu, C.; Li, G.; Tao, M.; Zhang, W. Synthesis 2013, 45,
7. Liégault, B.; Lapointe, D.; Caron, L.; Vlassova, A.; Fagnou, K.
8. Ishiwata, Y.; Togo, H. Synlett 2008, 2637–2641.
30.Tani, S.; Uehara, T. N.; Yamaguchia, J.; Itami, K. Chem. Sci. 2014, 5,
9. Narender, M.; Reddy, M. S.; Kumar, V. P.; Srinivas, B.; Sridhar, R.;
Nageswar, Y. V. D.; Rao, K. R. Synthesis 2007, 3469–3472.
31.Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D.
32.Zhou, G.-L.; Tams, D. M.; Marder, T. B.; Valentine, R.; Whiting, A.;
Przyborski, S. A. Org. Biomol. Chem. 2013, 11, 2323–2334.
10.Kazmaier, U.; Ackermann, S. Org. Biomol. Chem. 2005, 3, 3184–3187.
11.Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N.
12.Miwatashi, S.; Arikawa, Y.; Kotani, E.; Miyamoto, M.; Naruo, K.;
Kimura, H.; Tanaka, T.; Asahi, S.; Ohkawa, S. J. Med. Chem. 2005, 48,
13.Choi, Y.; Kawazoe, Y.; Murakami, K.; Misawa, H.; Uesugi, M.
882