3-(N-Methylcarbamoyl)-5-phenyl-1,2,4-oxadiazole (3e). Re-
Notes and references
crystallized from benzene. Colorless needles. Mp 132–133 ◦C. IR
1 A. Padwa, W. H. Pearson, E. C. Taylor and P. Wipf, Synthetic Appli-
cation of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and
Natural Products, Wiley-Interscience (2002); G. Molteni, Heterocycles,
2006, 68, 2177; S. Kanemasa, Sci. Synth., 2004, 19, 17; C. J. Easton,
C. M. M. Hughes, G. P. Savage and G. W. Simpson, Cycloaddition
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60, pp. 261–327, Academic Press (1994).
1
(Nujol) 1684 cm-1; H NMR (400 MHz, CDCl3) d 3.09 (d, J =
5.0 Hz, 3H), 7.0–7.2 (br, 1H), 7.56 (dd, J = 7.5, 7.5 Hz, 2H),
7.63 (t, J = 7.5 Hz, 1H), 8.17 (d, J = 7.5 Hz, 2H); 13C NMR
(100 MHz, CDCl3) d 25.6 (CH3), 122.4 (C), 127.5 (CH), 128.4
(CH), 132.6 (CH), 156.2 (C), 163.0 (C), 175.9 (C); MS (EI) 203
(M+, 100), 202 (75), 192 (90). HRMS Calcd. for C10H9N3O2:
203.0695, Found: 203.0689. Anal. Calcd for C10H9N3O2: C, 59.11;
H, 4.46; N, 20.68%. Found: C, 59.12; H, 4.50; N, 20.60%.
2 K. Hemming, Sci. Synth., 2004, 13, 127; K. Hemming, J. Chem. Res.,
2001, 209.
3 U. Groselj, D. Bevk, R. Jakse, A. Meden, B. Stanovnik and J. Svete,
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S. G. Grdadolnik and J. Svete, Arkivoc, 2003, xiv, 37; R. E. Bolton, S. J.
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Kabakchi, V. V. Il’in, A. V. Ignatenko and V. A. Ponomarenko, Russ.
Chem. Bull., 1992, 41, 1453.
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2009, 26, 1683.
5 G. Gelli, E. Cadoni, A. Deriu and P. Beltrame, J. Chem. Soc., Perkin
Trans. 2, 1990, 245.
6 S. G. Zlotin, A. I. Podgurskii, N. V. Airapetova and O. A. Luk’yanov,
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V. A. Ogurtsov, O. A. Rakitin, N. V. Obruchnikova, L. F. Chertanova,
A. A. Gazikasheva and L. I. Khmel’nitskii, Bull. Acad. Sci. USSR, Div.
Chem. Sci. (Engl. Transl.), 1990, 39, 1896.
5-(4-Methoxyphenyl)-3-(N-methylcarbamoyl)-1,2,4-oxadiazole
(3g). Recrystallized from benzene. Colorless needles. Mp 148–
149 ◦C. IR (Nujol) 1674 cm-1; 1H NMR (400 MHz, CDCl3) d 3.08
(d, J = 5.0 Hz, 3H), 3.91 (s, 3H), 7.03 (d, J = 8.7 Hz, 2H), 7.0–7.2
(br, 1H), 8.11 (d, J = 8.7 Hz, 2H); 13C NMR (100 MHz, CDCl3)
d 26.4 (CH3), 55.6 (CH3), 114.7 (CH), 115.8 (C), 125.9 (C), 130.3
(CH), 157.3 (C), 163.7 (C), 176.6 (C); MS (EI) 233 (M+, 100).
HRMS Calcd. for C11H11N3O3: 233.0800, Found: 233.0797. Anal.
Calcd for C11H11N3O3: C, 56.65; H, 4.75; N, 18.02%. Found: C,
56.61; H, 4.85; N, 18.04%.
5-(4-Chlorophenyl)-3-(N -methylcarbamoyl)-1,2,4-oxadiazole
(3i).◦ Recrystallized from benzene. Colorless needles. Mp 175–
177 C. IR (Nujol) 1674 cm-1; 1H NMR (400 MHz, CDCl3) d 3.09
(d, J = 5.2 Hz, 3H), 7.11 (br s, 1H), 7.55 (d, J = 8.8 Hz, 2H), 8.12
(d, J = 8.8 Hz, 2H); 13C NMR (100 MHz, CDCl3) d 26.5 (CH3),
121.7 (C), 129.6 (CH), 129.7 (CH), 140.1 (C), 156.9 (C), 163.9
(C), 175.9 (C); MS (EI) 237 (M+, 100), 239 (M++2, 33). HRMS
Calcd. for C10H8N3O2Cl: 237.0305, Found: 237.0304. Anal. Calcd
for C10H8N3O2Cl: C, 50.54; H, 3.39; N, 17.68%. Found: C, 50.91;
H, 3.05; N, 17.97%.
7 N. A. Bokach, V. Y. Kukushkin, M. Haukka and A. J. L. Pombeiro,
Eur. J. Inorg. Chem., 2005, 845; N. A. Bokach, A. V. Khripoun, V. Y.
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Chem. Ber., 1993, 126, 109.
8 S. Morrocchi, A. Ricca and L. Velo, Tetrahedron Lett., 1967, 8, 331.
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Paton, J. Chem. Soc., Chem. Commun., 1976, 240; M. Fetizon, M.
Golfier, R. Milcent and I. Paradakis, Tetrahedron, 1975, 31, 165.
10 Nitroisoxazolone 2 showed versatile reactivity to afford polyfunction-
alized compounds (see also ref. 11–13) M. Tamura, Y. Ise, Y. Okajima,
N. Nishiwaki and M. Ariga, Synthesis, 2006, 3453.
11 N. Nishiwaki, Y. Okajima, M. Tamura, N. Asaka, K. Hori, Y. Tohda
and M. Ariga, Heterocycles, 2003, 60, 303.
12 N. Nishiwaki, M. Nakanishi, T. Hida, Y. Miwa, M. Tamura, K. Hori,
Y. Tohda and M. Ariga, J. Org. Chem., 2001, 66, 7535.
3-(N-Methylcarbamoyl)-5-(3-pyridyl)-1,2,4-oxadiazole
(3j).
Recrystallized from CHCl3. Orange needles. Mp 188–190 ◦C. IR
1
(Nujol) 1674 cm-1; H NMR (400 MHz, CDCl3) d 3.11 (d, J =
13 The ammonolysis of nitroisoxazolone
2 afforded an oxime of
glyoxylamide11 which was converted to 3-functionalized 1,2,4-
5.1 Hz, 3H), 7.0–7.2 (br, 1H), 7.54 (dd, J = 7.9, 5.0 Hz, 1H), 8.47
(ddd, J = 7.9, 1.8, 1.6 Hz, 1H), 8.88 (dd, J = 5.0, 1.6 Hz, 1H), 9.42
(d, J = 1.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) d 26.5 (CH3),
119.9 (C), 124.0 (CH), 135.5 (CH), 149.2 (CH), 153.9 (CH), 156.7
(C), 164.0 (C), 174.8 (C); MS (EI) 204 (M+, 30), 203 (100). HRMS
Calcd. for C9H8N4O2: 204.0647, Found: 204.0629. Anal. Calcd
for C9H8N4O2: C, 52.94; H, 3.95; N, 27.44%. Found: C, 52.89; H,
3.94; N, 27.31%.
oxadiazoles 3 by O-acylation and cyclization.10.
14 N. Nishiwaki, K. Kobiro, H. Kiyoto, S. Hirao, J. Sawayama, K. Saigo,
Y. Okajima, T. Uehara, A. Maki and M. Ariga, Org. Biomol. Chem.,
2011, 9, 2832.
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Romeo, Tetrahedron, 1996, 52, 7885.
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J. Heterocycl. Chem., 1985, 22, 797; A. Corsaro, U. Chiacchio, P.
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McElroy, J. E. Mills, C. Reed and R. Webster, Bioorg. Med. Chem.
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2007, 50, 3442.
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19 K. Fukatsu, J. Kunitomo, Y. Kawano, T. Yamashita and T. Yamauchi,
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3-(N-Methylcarbamoyl)-5-(4-pyridyl)-1,2,4-oxadiazole
(3k).
Recrystallized from benzene. Orange granules. Mp 195–196 ◦C. IR
1
(Nujol) 1684 cm-1; H NMR (400 MHz, CDCl3) d 3.11 (d, J =
5.0 Hz, 3H), 7.0–7.2 (br, 1H), 8.03 (d, J = 4.5 Hz, 2H), 8.12 (d, J =
4.5 Hz, 2H); 13C NMR (100 MHz, CDCl3) d 28.7 (CH3), 123.5
(CH), 132.3 (C), 153.4 (CH), 158.7 (C), 166.4 (C), 177.1 (C);
MS (EI) 204 (M+, 51), 203 (100). HRMS Calcd. for C9H8N4O2:
204.0647, Found: 204.0633. Anal. Calcd for C9H8N4O2: C, 52.94;
H, 3.95; N, 27.44%. Found: C, 52.71; H, 3.95; N, 27.22%.
20 S. Harmsen, H. M. M. Bastiaans, W. Schaper, J. Tibes, U. Doller, D.
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Acknowledgements
We are grateful to Prof. Satoshi Minakata, Osaka University,
Japan for his kind assistance.
6754 | Org. Biomol. Chem., 2011, 9, 6750–6754
This journal is
The Royal Society of Chemistry 2011
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