I
M. Baenziger et al.
Paper
Synthesis
1H NMR (400 MHz, DMSO): δ = 8.31 (s, 1 H), 8.01 (d, J = 8.5 Hz, 2 H),
7.48 (d, J = 9.0 Hz, 1 H), 7.38 (t, J = 7.8 Hz, 2 H), 7.13 –7.31 (m, 3 H),
6.66 (d, J = 6.8 Hz, 1 H), 6.43 (br s, 1 H), 6.19 (br s, 1 H), 2.65 (s, 3 H).
13C NMR (100 MHz, DMSO): δ = 150.7 (dd, J = 243.5, 13.9 Hz), 146.0
(dd, J = 8.5 Hz), 143.9, 142.9 (dd, J = 234.2, 13.1 Hz), 139.3, 136.5,
133.6, 128.9 (2C), 128.2, 127.1 (2C), 126.4, 119.6, 118.8 (d,
J = 17.7 Hz), 115.6, 114.2, 108.8, 101.8 (d, J = 20.0 Hz), 18.8.
19F NMR (377 MHz, DMSO): δ = –137.1 (d, J = 23.2 Hz), –152.6 (d,
J = 23.0 Hz).
HR-LC MS: m/z [M + H]+ calcd for C20H16F2N3+: 336.1312; found:
J. J.; Balakirev, M. Y. J. Am. Chem. Soc. 2011, 133, 10058.
(i) Guasconi, M.; Lu, X.; Massarotti, A.; Caldarelli, A.; Ciraolo, E.;
Tron, G. C.; Hirsch, E.; Sorba, G.; Pirali, T. Org. Biomol. Chem.
2011, 9, 4144. (j) Akritopoulou-Zanze, I.; Wakefield, B. D.;
Gasiecki, A.; Kalvin, D.; Johnson, E. F.; Kovar, P.; Djuric, S. W.
Bioorg. Med. Chem. Lett. 2011, 21, 1480. (k) Buckmelter, A. J.;
Ren, L.; Laird, E. R.; Rast, B.; Miknis, G.; Wenglowsky, S.;
Schlachter, S.; Welch, M.; Tarlton, E.; Grina, J.; Lyssikatos, J.;
Brandhuber, B. J.; Morales, T.; Randolph, N.; Vigers, G.;
Martinson, M.; Callejo, M. Bioorg. Med. Chem. Lett. 2011, 21,
1248. (l) Guchhait, S. K.; Madaan, C. Org. Biomol. Chem. 2010, 8,
3631. (m) Al-Tel, T. H.; Al-Qawasmeh, R. A.; Voelter, W. Eur. J.
Org. Chem. 2010, 5586. (n) Guchhait, S.; Madaan, C. Synlett
2009, 628. (o) Krasavin, M.; Tsirulnikov, S.; Nikulnikov, M.;
Sandulenko, Y.; Bukhryakov, K. Tetrahedron Lett. 2008, 49, 7318.
(p) Kercher, T.; Rao, C.; Bencsik, J. R.; Josey, J. A. J. Comb. Chem.
2007, 9, 1177. (q) Shaabani, A.; Soleimani, E.; Maleki, A. Monatsh.
Chem. 2007, 138, 73. (r) Masquelin, T.; Bui, H.; Brickley, B.;
Stephenson, G.; Schwerkoske, J.; Hulme, C. Tetrahedron Lett.
2006, 47, 2989. (s) Parchinsky, V. Z.; Shuvalova, O.; Ushakova,
O.; Kravchenko, D. V.; Krasavin, M. Tetrahedron Lett. 2006, 47,
947. (t) Lu, Y.; Zhang, W. QSAR Comb. Sci. 2004, 23, 827.
(u) Ireland, S. M.; Tye, H.; Whittaker, M. Tetrahedron Lett. 2003,
44, 4369. (v) Blackburn, C.; Guan, B. Tetrahedron Lett. 2000, 41,
1495. (w) Varma, R. S.; Kumar, D. Tetrahedron Lett. 1999, 40,
7665.
336.1310.
Acknowledgment
The skilful work and support of our technical staff (J. Keusch, F. Navarro)
is gratefully acknowledged. We thank C. Guenat for measuring the
HR-LC/MS spectra and the structure elucidation group of NIBR for
their generous support and help.
Supporting Information
Supporting information for this article is available online at
S
u
p
p
ortiInfogrmoaitn
S
u
p
p
ortioInfgrmoaitn
(6) (a) Nagle, A.; Wu, T.; Kuhen, K.; Gagaring, K.; Borboa, R.;
Francek, C.; Chen, Z.; Plouffe, D.; Lin, X.; Caldwell, C.; Ek, J.;
Skolnik, S.; Liu, F.; Wang, J.; Chang, J.; Li, C.; Liu, B.; Hollenbeck,
T.; Tuntland, T.; Isbell, J.; Chuan, T.; Alper, P. B.; Fischli, C.; Brun,
R.; Lakshminarayana, S. B.; Rottmann, M.; Diagana, T. T.;
Winzeler, E. A.; Glynne, R.; Tully, D. C.; Chatterjee, A. K. J. Med.
Chem. 2012, 55, 4244. (b) Wu, T.; Nagle, A.; Kuhen, K.; Gagaring,
K.; Borboa, R.; Francek, C.; Chen, Z.; Plouffe, D.; Goh, A.;
Lakshminarayana, S. B.; Wu, J.; Ang, H. Q.; Zeng, P.; Kang, M. L.;
Tan, W.; Tan, M.; Ye, N.; Lin, X.; Caldwell, C.; Ek, J.; Skolnik, S.;
Liu, F.; Wang, J.; Chang, J.; Li, C.; Hollenbeck, T.; Tuntland, T.;
Isbell, J.; Fischli, C.; Brun, R.; Rottmann, M.; Dartois, V.; Keller,
T.; Diagana, T.; Winzeler, E.; Glynne, R.; Tully, D. C.; Chatterjee,
A. K. J. Med. Chem. 2011, 54, 5116.
(7) Adib, M.; Mahdavi, M.; Noghani, M. A.; Mirzaei, P. Tetrahedron
Lett. 2007, 48, 7263.
(8) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
(9) Chan, A. K.-W.; Wong, K. M.-C.; Yam, V. W.-W. J. Am. Chem. Soc.
2015, 137, 6920.
(10) Zakrzewski, J.; Huras, B.; Kiełczewska, A. Synthesis 2016, 48, 85.
(11) Lygin, A. V.; de Meijere, A. Org. Lett. 2009, 11, 389.
(12) Polisar, J. G.; Norton, J. R. Tetrahedron 2012, 68, 10236.
(13) Wang, J.; Rosingana, M.; Discordia, R. P.; Soundararajan, N.;
Polniaszek, R. Synlett 2001, 1485.
References
(1) New address: E. Durantie, Adolphe Merkle Institute, BioNano-
material, Chemin des Verdiers 4, 1700 Fribourg, Switzerland.
(2) Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661.
(3) Blackburn, C.; Guan, B.; Fleming, P.; Shiosaki, K.; Tsai, S. Tetrahe-
dron Lett. 1998, 39, 3635.
(4) Bienaymé, H.; Bouzid, K. Angew. Chem. Int. Ed. 1998, 37, 2234.
(5) (a) Zhang, W.; Lu, Y.; Scott, P. J. H. In Solid-Phase Organic Synthe-
ses; Scott, P. J. H., Ed.; John Wiley & Sons, Inc: Hoboken, 2012,
51–57. (b) Ramesha, A. B.; Raghavendra, G. M.; Nandeesh, K. N.;
Rangappa, K. S.; Mantelingu, K. Tetrahedron Lett. 2013, 54, 95.
(c) Guchhait, S. K.; Chaudhary, V.; Madaan, C. Org. Biomol. Chem.
2012, 10, 9271. (d) Shukla, N. M.; Salunke, D. B.; Yoo, E.; Mutz, C.
A.; Balakrishna, R.; David, S. A. Bioorg. Med. Chem. 2012, 20,
5850. (e) Hieke, M.; Rödl, C. B.; Wisniewska, J. M.; laBuscató, E.;
Stark, H.; Schubert-Zsilavecz, M.; Steinhilber, D.; Hofmann, B.;
Proschak, E. Bioorg. Med. Chem. Lett. 2012, 22, 1969. (f) Tyagi, V.;
Khan, S.; Bajpai, V.; Gauniyal, H. M.; Kumar, B.; Chauhan, P. M. S.
J. Org. Chem. 2012, 77, 1414. (g) Baviskar, A. T.; Madaan, C.;
Preet, R.; Mohapatra, P.; Jain, V.; Agarwal, A.; Guchhait, S. K.;
Kundu, C. N.; Banerjee, U. C.; Bharatam, P. V. J. Med. Chem. 2011,
54, 5013. (h) Burchak, O. N.; Mugherli, L.; Ostuni, M.; Lacapère,
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–I