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chromatography, which afforded the corresponding products in
good to moderate yields (45–98%).
4 (a) H. Firouzabadi, N. Iranpoor, S. Sobhani, S. Gassamipour
and Z. Amoozgar, Tetrahedron Lett., 2003, 44, 891; (b)
T. S. Jin, R. F. Tian, L. B. Liu, Y. Zhao and T. S. Li, Synth.
Commun., 2006, 36, 1823; (c) H. R. Shaterian,
F. Shahrekipoor and M. Ghashang, J. Mol. Catal. A: Chem.,
2007, 272, 142.
5 (a) G. Sartori and R. Maggi, Chem. Rev., 2010, 113, 1; (b)
M. M. Mojtahedi, H. Abbasi and M. S. Abaee, J. Mol. Catal.
A: Chem., 2006, 250, 6; (c) H. Firouzabadi, N. Iranpoor,
S. Sobhani and S. Gassamipour, Synthesis, 2005, 595.
6 (a) R. Kuhn, I. Low and H. Trishmann, Chem. Ber., 1957, 90,
203; (b) S. Czernecki, C. Georgoulis and C. Provelenghiou,
Tetrahedron Lett., 1976, 17, 3535; (c) B. Classon,
P. J. Garegg, S. Oscarson and A. K. Tidem, Carbohydr. Res.,
1991, 216, 187; (d) P. Eckenberg, T. Groth, T. Huhn,
N. Richter and C. Schemck, Tetrahedron, 1993, 49, 1619; (e)
H.-P. Wessell, T. Iversen and D. R. Bundle, J. Chem. Soc.,
Perkin Trans. 1, 1985, 1, 2247.
7 (a) D. L. Hjeressen, D. L. Schutt and J. M. Boese, J. Chem.
Educ., 2000, 77, 1543; (b) L.-J. Ma and T. Inokuchi, Chem.
Commun., 2010, 46, 7037; (c) For reviews dealing with
microwave-assisted green and sustainable chemistry see:
R. S. Varma, Green Chem., 1999, 1, 43; (d) C. R. Strauss,
Aust. J. Chem., 1999, 52, 83; (e) V. Polshettiwar and
R. S. Varma, Chem. Soc. Rev., 2008, 37, 1546; (f) H.-M. Guo,
P.-Y. Xin, H.-Y. Niu, D.-C. Wang, Y. Jiang and G.-R. Qu,
Green Chem., 2010, 12, 2131.
Spectroscopic data for selected compounds 3a
IR (CH2Cl2) gmax: 1130, 1361, 1476, 1492, 1619, 1721, 1732,
2126, 2931, 3218 cmꢁ1; 1H NMR (CDCl3/TMS, 500.1 MHz): d 2.03
(s, 3H), 3.27 (s, 3H), 3.77 (s, 3H), 6.50 (s, 1H), 6.57 (s, 1H), 6.91
(d, J ¼ 7 Hz, 1H), 7.20 (s, 1H), 7.60 (s, 1H), 7.79 (d, J ¼ 7 Hz, 1H);
13C NMR (CDCl3/TMS, 75.3 MHz): d 20.52, 26.99, 54.87, 78.29,
108.29, 115.52, 122.80, 127.61, 129.06, 131.61, 135.47, 135.87,
165.68, 169.87, 173.01; FAB mass: calcd for C15H15NO5 is 289.10;
found: 290.47 (M + 1).
Compound 3f
IR (CH2Cl2) gmax: 1134, 1233, 1354, 1475, 1470, 1613, 1724,
1735, 2122, 2928, 3210 cmꢁ1; 1H NMR (CDCl3/TMS, 500.1 MHz):
d 2.35 (s, 1H), 3.27 (s, 3H), 3.57 (s, 3H), 3.88–4.03 (m, 2H), 6.62
(s, 2H), 6.85–6.87 (d, J ¼ 7.5 Hz, 1H), 7.04–7.06 (t, J ¼ 7.0 Hz,
1H), 7.12–7.14 (d, J ¼ 7.5 Hz, 1H), 7.34–7.34 (t, J ¼ 7.0 Hz, 1H);
13C NMR(CDCl3/TMS, 75.3 MHz): d 26.46, 51.95, 52.91, 74.62,
79.10, 80.41, 108.47, 122.89, 124.55, 125.96, 128.51, 130.75,
137.42, 145.34, 164.57, 173.43; FAB mass: calcd for C16H15NO4 is
285.12; found: 286.32 (M + 1).
Acknowledgements
KS thanks SIT Kariapatti for providing lab facilities. RVLV
thanks the directors of NIIST for providing infrastructure
facilities. Thanks are due to Mrs Viji and Mrs Saumini Mathew
for providing Mass and NMR spectra.
8 (a) M. Csiba, J. Cleophax, A. Loupy, J. Malthete and
S. D. Gero, Tetrahedron Lett., 1993, 34, 1787; (b)
D. Villemin, A. B. Alloum and F. Thibault-Starzyk, Synth.
Commun., 1992, 22, 1359; (c) M. J. Perio, R. Dozias,
P. Jacquault and J. Hamelin, Tetrahedron Lett., 1997, 38,
7867.
9 (a) G. Bashiardes, I. Sar, A. S. Mohamed, F. Barbot and
J. Laduranty, Org. Lett., 2003, 5, 4915; (b) S. Caddick,
A. J. McCarrolla and D. A. Sandham, Tetrahedron, 2001, 57,
6305; (c) J. Wettergren and A. B. E. Minidis, Tetrahedron
Lett., 2003, 44, 7611.
Notes and references
1 (a) T. W. Greene and P. G. M. Wuts, Protective Groups in
Organic Synthesis, Wiley, New York, 1991; (b)
P. J. Kocienski, Protecting Groups, Springer, New York, 1994;
(c) M. R. Paleo, N. Aurrecoechea, K.-Y. Jung and
H. Rapoport, J. Org. Chem., 2003, 68, 130; (d) R. Ramesh, 10 (a) K. Selvakumar, V. Vaithiyanathan and P. Shanmugam,
R. G. Bhat and S. Chandrasekaran, J. Org. Chem., 2005, 70,
837; (e) G. Wang, J. R. E. Menye, M. Martin, H. Yang and
K. Williams, Org. Lett., 2008, 10, 4203; (f) C. L. Morris,
Y. Hu, G. D. Head, L. J. Brown, W. G. Whittingham and
R. C. D. Brown, J. Org. Chem., 2009, 74, 981; (g)
M. Schelhaas and H. Waldmann, Angew. Chem., Int. Ed.,
Chem. Commun., 2010, 46, 2826; (b) B. Viswambharan,
K. Selvakumar, S. Madhavan and P. Shanmugam, Org.
Lett., 2010, 12, 2108; (c) P. Shanmugam, B. Viswambharan,
K. Selvakumar and S. Madhavan, Tetrahedron Lett., 2008,
49, 2611; (d) Due to the hygroscopic nature of dry pyridine,
the preparation of dry pyridine required special care.
1996, 35, 2056; (h) D. Vadolas, H. P. Germann, S. Thakur, 11 (a) P. Shanmugam and P. Rajasingh, Tetrahedron, 2004, 60,
W. Keller and E. Heidemann, Int. J. Pept. Protein Res., 1985,
25, 554; (i) P. M. Fischer, K. V. Retson, M. I. Tyler and
M. E. H. Howden, Int. J. Pept. Protein Res., 1991, 38, 491.
2 (a) J. Cossy and P. Pale, Tetrahedron Lett., 1987, 28, 6039; (b)
9283; (b) S. C. Kim, S. Gowrisankar and J. N. Kim,
Tetrahedron Lett., 2006, 47, 3463; (c) Y.-L. Liu, B.-L. Wang,
J.-J. Cao, L. Chen, Y.-X. Zhang, C. Wang and J. Zhou, J. Am.
Chem. Soc., 2010, 132, 15176.
M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati and 12 P. Shanmugam, V. Vaithiyanathan and B. Viswambharan,
U. Costantino, Synth. Commun., 1999, 29, 541; (c)
H. Firouzabadi, N. Iranpoor, K. Amani and F. Nowrouzi, J.
Chem. Soc., Perkin Trans. 1, 2002, 1, 2601.
Tetrahedron,
2006,
62,
4342;
P.
Shanmugam,
V. Vaithiyanathan and B. Viswambharan, Aust. J. Chem.,
2007, 60, 296; P. Shanmugam and B. Viswambharan,
Synlett, 2008, 2763.
3 (a) B. Karimi and B. Golshani, J. Org. Chem., 2000, 65, 7228;
(b) N. Azizi and M. R. Saidi, Organometallics, 2004, 23, 1457; 13 (a) J. Peng, X. Huang, H.-L. Cui and Y.-C. Chen, Org. Lett.,
(c) B. Akhlaghinia and S. Tavakoli, Synthesis, 2005, 1775.
2010, 12, 4260; (b) J. Barluenga, G. Lonzi, L. Riesgo,
36542 | RSC Adv., 2014, 4, 36538–36543
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