Beilstein J. Org. Chem. 2011, 7, 1745–1752.
1-Phenylmethyl-2-[(4-phenyl-1,2,3-triazol-1-
yl)methyl]aziridine (15a)
5. Harrison, T.; Samuel, B. U.; Akompong, T.; Hamm, H.; Mohandas, N.;
Lomasney, J. W.; Haldar, K. Science 2003, 301, 1734.
Rf 0.23 (CHCl3/MeOH 98:2), viscous light-brown oil, 61%.
1H NMR (300 MHz, CDCl3) δ 1.65 (d, J = 6.6 Hz, 1H), 1.88 (d,
J = 3.3 Hz, 1H), 2.01–2.08 (m, 1H), 3.09 and 3.67 (2 d, J =
12.9 Hz, 2H), 3.93 and 4.70 (2 dd, J = 14.3, 8.2, 3.3 Hz, 2H),
7.06–7.43 (m, 8H), 7.49 (s, 1H), 7.66–7.69 (m, 2H); 13C NMR
(75 MHz, CDCl3) δ 32.4, 38.3, 53.5, 64.5, 119.9, 125.9, 127.7,
128.1, 128.4, 128.6, 128.7, 130.8, 138.2, 147.9; IR (cm−1) νmax:
2919, 1453, 1358, 1225, 1075, 1046, 1027, 763, 731, 694; MS
(70 eV) m/z (%): 291 (M+ + 1, 100); HRMS (ESI): [M + H]+
calcd for C18H19N4, 291.1610; found, 291.1613.
6. D’hooghe, M.; Dekeukeleire, S.; Mollet, K.; Lategan, C.; Smith, P. J.;
Chibale, K.; De Kimpe, N. J. Med. Chem. 2009, 52, 4058.
7. Pérez-Silanes, S.; Berrade, L.; García-Sánchez, R. N.; Mendoza, A.;
Galiano, S.; Pérez-Solórzano, B. M.; Nogal-Ruiz, J. J.;
Martínez-Fernández, A. R.; Aldana, I.; Monge, A. Molecules 2009, 14,
8. D’hooghe, M.; Kenis, S.; Vervisch, K.; Lategan, C.; Smith, P. J.;
Chibale, K.; De Kimpe, N. Eur. J. Med. Chem. 2011, 46, 579.
9. Zwanenburg, B.; ten Holte, P. Top. Curr. Chem. 2001, 216, 93.
12.Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
3-Diethylamino-2-(phenylmethyl)amino-1-(4-
phenyl-1,2,3-triazol-1-yl)propane (16a)
Rf 0.19 (CHCl3/MeOH 97:3), light-brown oil, 56%. 1H NMR
(300 MHz, CDCl3) δ 0.92 (t, J = 7.2 Hz, 6H), 2.26–2.52 (m,
6H), 3.05–3.13 (m, 1H), 3.74 and 3.81 (2 d, J = 13.5 Hz, 2H),
4.36 and 4.44 (2 dd, J = 14.2, 4.9, 4.7 Hz, 2H), 7.21–7.44 and
7.82–7.84 (2 m, 10H), 7.86 (s, 1H); 13C NMR (75 MHz,
CDCl3) δ 11.8, 47.1, 52.0, 52.3, 55.0, 55.4, 121.2, 125.8, 127.2,
13.Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
14.McCoull, W. M.; Davis, F. A. Synthesis 2000, 1347.
15.Watson, I. D. G.; Yu, L.; Yudin, A. K. Acc. Chem. Res. 2006, 39, 194.
128.1, 128.2, 128.6, 128.9, 130.9, 140.2, 147.5; IR (cm−1) νmax: 16.Padwa, A.; Murphree, S. S. ARKIVOC 2006, No. iii, 6.
17.Singh, G. S.; D’hooghe, M.; De Kimpe, N. Chem. Rev. 2007, 107,
2967, 1462, 1454, 1073, 762, 734, 694; MS (70 eV) m/z (%):
364 (M+ + 1, 100); HRMS (ESI): [M + H]+ calcd for
18.Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377.
C22H30N5, 364.2501; found, 364.2503.
19.Alcaide, B.; Almendros, P. Synlett 2002, 381.
Supporting Information
20.Fisher, J. F.; Meroueh, S. O.; Mobashery, S. Chem. Rev. 2005, 105,
Supporting Information File 1
21.Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107,
Experimental procedures and characterization data.
23.Singh, G. S. Tetrahedron 2003, 59, 7631.
24.Singh, G. S.; D'hooghe, M.; De Kimpe, N. In Comprehensive
Heterocyclic Chemistry III; Katritzky, A.; Ramsden, C.; Scriven, E.;
Taylor, R., Eds.; Elsevier: Oxford, 2008; Vol. 2, p 1.
Acknowledgements
The authors are indebted to the “Research Foundation – Flan-
ders” (FWO-Vlaanderen), the “Institute for the Promotion of
Innovation through Science and Technology – Flanders” (IWT-
Vlaanderen), and to Ghent University (GOA) for financial
support.
25.Xing, B.; Rao, J.; Liu, R. Mini-Rev. Med. Chem. 2008, 8, 455.
26.Aranda, M. T.; Perez-Faginas, P.; Gonzalez-Muniz, R.
27.D’hooghe, M.; Dekeukeleire, S.; Leemans, E.; De Kimpe, N.
28.Van Driessche, B.; Van Brabandt, W.; D’hooghe, M.; Dejaegher, Y.;
De Kimpe, N. Tetrahedron 2006, 62, 6882.
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