1820
N. V. Lakshmi, P. T. Perumal / Tetrahedron Letters 54 (2013) 1817–1820
9
9
5. (a) Quintás, D.; Garc
i
a, A.; Dom
i
nguez, D. Tetrahedron Lett. 2003, 44, 9291; (b)
was cleaved by the secondary amino acids serendipitously. The
simplicity of the approach makes this strategy useful for the syn-
thesis of novel pyrrolidinones and pyrrolizidinones. Further studies
to delineate the scope and limitations of the present methodology
are underway.
Gemma, S.; Campiani, G.; Butini, S.; Morelli, E.; Minetti, P.; Tinti, O.; Nacci, V.
Tetrahedron 2002, 58, 3689.
6. González, M.; Segura, J. L.; Seoane, C.; Martín, N. J. Org. Chem. 2001, 66, 8872.
7. Spectral data of compound 3j: 1H NMR (500 MHz, DMSO-d6): d 7.33–7.35 (d, 2H,
J = 8.40 Hz, –Ar–H), 7.56–7.61 (m, 3H, –Ar–H), 7.61–7.65 (m, 2H, –Ar–H), 7.72
(s, 1H, @CH), 8.25–8.27 (d, 2H, J = 8.40 Hz, –Ar–H), 8.31–8.34 (m, 3H,–Ar–H).
13C NMR (125 MHz, DMSO-d6): d 117.2, 123.2, 126.2, 126.3, 126.8, 127.9, 128.8,
129.1, 129.3, 130.1, 132.3, 134.5, 136.4, 137.1, 138.9, 140.2, 154.1, 164.5, 168.6.
8. Lee, S.; Jung, S. Carbohydr. Res. 2004, 339, 461.
Acknowledgment
9. Crich, D.; Bowers, A. A. Org. Lett. 2007, 9, 5323.
One of the authors, N.V.L. thanks the Council of Scientific and
Industrial Research (CSIR), New Delhi, India for the research
fellowship.
10. Typical experimental procedure for 5j:
A mixture of 2-naphthaldehyde 1j
(1.0 mmol), 3-phenyl-5-isoxazolone 2 (1.0 mmol), sarcosine 4 (1.0 mmol) in
methanol was refluxed for 40 min and cooled to room temperature. The solid
formed in the reaction mixture was filtered, dried under vacuum. The crude
solid product was purified by recrystallization in methanol to obtain the pure
product 5j in good yield (80%).
Supplementary data
Spectral data of compound 5j: (Table 1, entry 10): White solid. Mp 202–204 °C.
Rf 0.3 (50% EtOAc/petroleum ether). mmax (KBr): 3218, 2369, 1714, 1436,
695 cmÀ1 1H NMR (500 MHz, DMSO-d6): d 2.85 (s, 3H, –NCH3), 3.51 (t, 1H,
.
Supplementary data associated with this article can be found, in
J = 9.2 Hz, –NCH), 3.90 (t, 1H, J = 9.2 Hz, –NCH), 4.54–4.56 (m, 1H, –CH), 4.76–
4.78 (m, 1H, CH), 7.20–7.22 (m, 5H, –Ar–H), 7.38–7.41 (m, 1H, –Ar–H), 7.43–
7.47 (m, 2H, –Ar–H), 7.73 (d, 1H, J = 7.7 Hz, –Ar–H), 7.78 (d, 1H, J = 7.7 Hz, –Ar–
H), 7.83–7.87 (m, 2H, –Ar–H), 11.66 (br s, 1H, –OH, D2O exchangeable). 13C
NMR (125 MHz, DMSO-d6): d 30.1, 36.9, 49.1, 54.8, 123.2, 124.7, 126.2, 126.3,
126.8, 127.9, 128.8, 129.0, 129.3, 131.9, 133.9, 136.6, 137.4, 154.1, 171.5. MS
(m/z): 345.0 M++1. Anal. Calcd for C22H20N2O2: C, 76.72; H, 5.85; N, 8.13.
Found: C, 76.78; H, 5.89; N, 8.18.
References and notes
1. (a) Sun, J.; Sun, Y.; Gong, H.; Xie, Y.-J.; Yan, C.-J. Org. Lett. 2012, 14, 5172; (b)
Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc.
Chem. Res. 1996, 29, 123; (c) Zhu, J.; Bienayme, H. Multicomponent Reactions;
Wiley: Weinheim, 2005; (d) D’Souza, D. M.; Muller, T. J. J. Chem. Soc. Rev. 2007,
36, 1095; (e) Tietze, L. F.; Kinzel, T.; Brazel, C. C. Acc. Chem. Res. 2009, 42, 367; (f)
Jiang, B.; Li, Q.-Y.; Tu, S.-J.; Li, G. Org. Lett. 2012, 14, 5210; (g) Zhu, Q.; Gao, L.;
Chen, Z.; Zheng, S.; Shu, H.; Li, J.; Jiang, H.; Liu, S. Eur. J. Med. Chem. 2012, 54,
232; (h) Brahmachari, G.; Das, S. Tetrahedron Lett. 2012, 53, 1479.
2. (a) Lakshmi, N. V.; Josephine, G. A. S.; Perumal, P. T. Tetrahedron Lett. 2012, 53,
1282; (b) Bhaskar, G.; Arun, Y.; Balachandran, C.; Saikumar, C.; Perumal, P. T.
Eur. J. Med. Chem. 2012, 51, 79; (c) Lakshmi, N. V.; Tamilisai, R.; Perumal, P. T.
Tetrahedron Lett. 2011, 52, 5301; (d) Kiruthika, S. E.; Lakshmi, N. V.; Banu, B. R.;
Perumal, P. T. Tetrahedron Lett. 2011, 52, 6508; (e) Lakshmi, N. V.; Arun, Y.;
Perumal, P. T. Tetrahedron Lett. 2011, 52, 3437.
11. Crystallographic data for compound 5k in this Letter have been deposited with
the Cambridge Crystallographic Data centre as supplemental publication no.
CCDC-904110. Copies of the data can be obtained, free of charge on application
to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Fax: +44 01223 336033 or
email: deposit@ccdc.cam.ac.uk.
12. Spectral data of compound 7a: (Table 2, entry 1): Green solid. Mp 220–222 °C. Rf
0.3 (50% EtOAc/petroleum ether). mmax (KBr): 3424, 1733, 1570, 1470,
1181 cmÀ1 1H NMR (500 MHz, DMSO-d6): d 1.50 (d, 1H, J = 10.2 Hz, –CH),
.
1.71 (d, 1H, J = 13.0 Hz, –CH), 2.06–2.08 (m, 1H, –CH), 2.64–2.66 (m, 2H, –CH2),
3.18 (d, 1H, J = 9.2 Hz, –CH), 3.92–3.94 (m, 1H, –CH), 4.20–4.21 (m, 1H, –CH),
4.37 (d, 1H, J = 9.2 Hz, –CH), 6.84 (d, 1H, J = 8.4 Hz, –Ar–H), 7.07–7.10 (m, 3H, –
Ar–H), 7.30–7.33 (m, 4H, –Ar–H), 7.37–7.39 (m, 2H, –Ar–H), 8.72 (br s, 1H, –OH,
D2O exchangeable). 13C NMR (125 MHz, DMSO-d6): d 17.6, 25.8, 34.7, 39.5,
53.2, 62.1, 126.4, 126.9, 127.9, 128.7, 129.1, 129.2, 130.6, 132.2, 133.4, 140.8,
163.5, 174.5. MS (m/z): 321.7 M++1. Anal. Calcd for C20H20N2O2: C, 74.98; H,
6.29; N, 8.74. Found: C, 74.92; H, 6.34; N, 8.78.
3. (a) Moriyama, K.; Izumisawa, Y.; Togo, H. J. Org. Chem. 2012, 77, 9846; (b) Li, G.;
Ding, Z.; Xu, B. Org. Lett. 2012, 14, 5338.
4. (a) Donohoe, T. J.; Chiu, J. Y. K.; Thomas, R. E. Org. Lett. 2007, 9, 421; (b) Liu, Z.;
Nefzi, A. J. Comb. Chem. 2010, 12, 566.