1903
H. A. Samimi, F. Dadvar
Paper
Synthesis
1H NMR (400 MHz, CDCl3): δ = 7.74–7.70 (m, 3 H), 7.65–7.64 (m, 1 H),
7.47–7.43 (m, 3 H), 7.40 (t, J = 8.0 Hz, 1 H), 7.38–7.33 (m, 1 H), 7.02
(ddd, J = 8.3, 2.6, 0.8 Hz, 1 H), 3.90 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 161.2, 160.0, 151.4, 130.1, 129.1,
128.8, 128.6, 128.1, 124.4, 123.6, 118.9, 117.0, 111.1, 55.6.
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2007, 9, 3461. (g) Pankova, A. S.; Voronin, V. V.; Kuznetsov, M. A.
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Nunes, C. M.; Pais, A. A. C. C.; Pinho e Melo, T. M. V. D.; Arnaut, L.
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Anal. Calcd for C16H13NO2: C, 76.48; H, 5.21; N, 5.77. Found: C, 76.32;
H, 5.12; N, 5.63.
2-(3-Chlorophenyl)-5-phenyloxazole (3j)
Yield: 227 mg (89%); white solid; mp 98–100 °C.
1H NMR (400 MHz, CDCl3): δ = 8.11–8.10 (m, 1 H), 8.01–7.98 (m, 1 H),
7.74–7.71 (m, 2 H), 7.47–7.42 (m, 5 H), 7.37–7.33 (m, 1 H).
13C NMR (100 MHz, CDCl3): δ = 159.9, 151.9, 135.1, 130.4, 130.3,
129.2, 129.1, 128.8, 127.9, 126.4, 124.5, 124.4, 123.7.
Anal. Calcd for C15H10ClNO: C, 70.46; H, 3.94; N, 5.48. Found: C, 70.24;
H, 3.86; N, 5.38.
(4) (a) Felix, D.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1968,
7, 224. (b) Zhong, Y.-L.; Bulger, P. G. Org. Synth. 2010, 87, 8.
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Zwanenburg, B. Tetrahedron Lett. 1995, 36, 4665. (h) Legters, J.;
Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111,
75.
(5) (a) Samimi, H. A.; Mohammadi, S. Synlett 2013, 24, 223.
(b) Keni, M.; Tepe, J. J. J. Org. Chem. 2005, 70, 4211. (c) Beletskii,
E. V.; Kuznetsov, M. A. Russ. J. Org. Chem. 2009, 45, 1229.
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Sottocornola, S. J. Org. Chem. 2008, 73, 4746. (e) Wang, S.-X.;
Wang, M.-X.; Wang, D.-X.; Zhu, J. Eur. J. Org. Chem. 2007, 4076.
(f) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4623. (g) Phillips,
A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Org. Lett. 2000,
2, 1165. (h) Pusch, S.; Opatz, T. Org. Lett. 2014, 16, 5430.
(i) Padwa, A.; Eisenhardt, W. Chem. Commun. 1968, 380.
(j) Padwa, A.; Eisenhardt, W. J. Am. Chem. Soc. 1968, 90, 2442.
(k) Padwa, A.; Eisenhardt, W. J. Am. Chem. Soc. 1971, 93, 1400.
(l) Lown, J. W.; Moser, J. P. J. Chem. Soc., Chem. Commun. 1970,
247. (m) Kuznetsov, M. A.; Voronin, V. V. Chem. Heterocycl.
Compd. 2011, 47, 173. (n) Padwa, A.; Eastman, D.; Hamilton, L.
J. Org. Chem. 1968, 33, 1317.
5-(4-Chlorophenyl)-2-phenyloxazole (3k)
Yield: 206 mg (81%); white solid; mp 78–80 °C.
IR (KBr): 3063, 2991, 1654, 1582, 825, 758, 691 cm–1
1H NMR (400 MHz, CDCl3): δ = 8.13 (d, J = 7.5 Hz, 2 H), 7.75 (d, J = 7.5
Hz, 2 H), 7.59–7.55 (m, 2 H), 7.50–7.37 (m, 4 H).
13C NMR (100 MHz, CDCl3): δ = 161.3, 150.3, 130.7, 128.8, 128.7,
128.4, 127.8, 127.2, 126.4, 124.3, 123.2.
.
Anal. Calcd for C15H10ClNO: C, 70.46; H, 3.94; N, 5.48. Found: C, 70.26;
H, 3.81; N, 5.37.
1-Benzyl-2-benzoyl-3-phenylaziridine (4a)
Yield: 225 mg (72%); white solid; mp 110–112 °C.
IR (KBr): 3100, 2994, 1668, 1595, 1495, 1000, 760, 690 cm–1
1H NMR (500 MHz, CDCl3): δ = 7.93 (d, J = 7.2 Hz, 2 H), 7.51 (m, 3 H),
7.42 (m, 6 H), 7.30 (t, J = 7.5 Hz, 1 H), 7.23 (t, J = 7.6 Hz, 2 H), 7.16 (t, J =
7.8 Hz, 1 H), 4.09 (d, J = 13.9 Hz, 1 H), 3.86 (d, J = 13.9 Hz, 1 H), 3.43 (d,
J = 7.2 Hz, 1 H), 3.35 (d, J = 7.2 Hz, 1 H).
.
13C NMR (125 MHz, CDCl3): δ = 193.6, 138.2, 135.4, 133.3, 128.8,
128.6, 128.4, 128.3, 127.9, 127.8, 127.6, 64.3, 51.2, 50.2.
Acknowledgment
(6) (a) Samimi, H. A.; Mamaghani, M.; Tabatabeian, K. J. Heterocycl.
Chem. 2008, 45, 1765. (b) Mamaghani, M.; Tabatabeian, K.;
Samimi, H. A. Z. Kristallogr. - New Cryst. Struct. 2008, 223, 390.
(c) Samimi, H. A.; Mohammadi, S. J. Iran Chem. Soc. 2013, 11, 69.
(d) Samimi, H. A.; Kiyani, H.; Shams, Z. J. Chem. Res. 2013, 282.
(e) Samimi H. A., Bohari M. Y., Hiedari Z., Narimani L.; J. Iran
Chem. Soc., in press. (f) Samimi, H. A.; Bohari, M. Y. J. Chem. Res.
2014, 38, 358. (g) Samimi, H. A.; Mohammadi, S. J. Iran Chem.
Soc. 2014, 11, 69. (h) Samimi, H. A.; Shams, Z. J. Iran Chem. Soc.
2014, 11, 979. (i) Samimi, H. A.; Bohari, M. Y.; Soltani, M. J. Iran
Chem. Soc. 2014, 11, 1467. (j) Samimi, H. A.; Salehi, E.; Dadvar, F.
J. Chem. Res. 2014, 38, 731. (k) Samimi, H. A.; Bohari, M. Y.;
Saberi, F. Synthesis 2015, 47, 129.
We are grateful to the Research Council of Shahrekord University for
supporting this work.
References
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 1899–1904