Karthikeyan and Perumal
1751
rahedron Lett. 29, 403 (1988); (c) W.D. Lubell, M. Kitamura,
and R. Noyori. Tetrahedron: Asymmetry, 2, 543 (1991); (d) G.
Bartoli, C. Cimarelli, E. Marcantoni, G. Palmieri, and M.
Petrini. J. Org. Chem. 59, 5328 (1994).
3H, J = 7.45 Hz), 2.59 (s, 3H), 2.65 (s, 3H), 4.04–4.09 (q,
2H, J = 7.45 Hz), 7.00 (s, 1H), 7.31–7.39 (m, 5H). 13C NMR
(125 MHz, CDCl3) δ: 13.6, 24.3, 27.7, 61.3, 121.3, 125.9,
127.9, 128.51, 128.57, 138.7, 148.7, 155.1, 158.6, 169.04.
MS (EI) m/z (%): 255 (95) [M+], 210 (90), 115 (100). Anal.
calcd. for C16H17NO2: C 75.27, H 6.71, N 5.49; found: C
75.41, H 6.83, N 5.40.
2. L.G. Beholtz, P. Benovsky, D.L. Ward, N.S. Barta, and J.R.
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Lett. 43, 2521 (2002); (c) H.A Stefani and E. de Avila. Synth.
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F.S. Letie, M.R.S. Nunes, and M.E. Payret-Arrua. Tetrahedron,
55, 10915 (1999).
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and S. Rault. Synthesis, 1740 (2002).
5. (a) C.J. Valduga, A. Squizani, H.S. Braibante, and M.E.F.
Braibante. Synthesis, 1019 (1998); (b) B. Rechsteiner, F.
Texier-Boullet, and J. Hamekin. Tetrahedron Lett. 34, 5071
(1993); (c) A. Arcadi, G. Bianchi, S. Di Giuseppe, and F.
Marinelli. Green Chem. 64 (2003); (d) A.R. Khosropour,
M.M. Khodaei, and M. Kookhazhdeh. Tetrahedron Lett. 45,
1725 (2004); (e) G. Bartoli, M. Boscp, M. Locatelli, E.
Marcantoni, P. Melchiorre, and L. Sambri. Synlett, 239 (2004).
6. (a) M.C. Bagley, J.W. Dale, and J. Bower. Synlett, 1149
(2001); (b) M.C. Bagley, J.W. Dale, D.D. Hughes, M.
Ohnesorge, N.G. Phillips, and J. Bower. Synlett, 1523 (2001);
(c) M.C. Bagley, C. Brace, J.W. Dale, M. Ohnesorge, N.G.
Phillips, X. Xiong, and J. Bower. J. Chem. Soc. Perkin Trans.
1, 1663 (2002).
Methyl 2,6-dimethylnicotinate (6b)
Rf 0.3 (20% EtOAc in petroleum ether). IR (neat, cm–1):
1
1720. H NMR (400 MHz, CDCl3) δ: 2.57 (s, 3H), 2.73 (s,
3H), 3.89 (s, 3H), 7.05–7.07 (s, 1H, J = 8 Hz), 8.08–8.10 (s,
1H, J = 8 Hz). 13C NMR (100 MHz, CDCl3) δ: 13.6, 24.3,
40.0, 120.8, 124.9, 139.1, 159.1, 161.0, 166.6. MS (EI) m/z
(%): 179 (60) [M+], 151 (100). Anal. calcd. for C10H13NO2:
C 67.02, H 7.31, N 7.82; found: C 66.91, H 7.44, N 7.89.
Methyl 2-methyl-4-phenylnicotinate (6c)
Rf 0.4 (20% EtOAc in petroleum ether). IR (neat, cm–1):
1
1720. H NMR (400 MHz, CDCl3) δ: 2.58 (s, 3H), 3.89 (s,
3H), 7.05–7.07 (s, 1H, J = 8 Hz), 8.08–8.10 (s, 1H, J =
8 Hz), 7.31–7.39 (m, 5H). 13C NMR (125 MHz, CDCl3) δ:
25.1, 45.1, 121.3, 125.9, 127.9, 128.51, 128.57, 138.7,
148.7, 155.1, 158.6, 162.5, 169.04. MS (EI) m/z (%): 227
(80) [M+], 115 (100). Anal. calcd. for C14H13NO2: C 73.99,
H 5.77, N 6.16; found: C 74.17, H 5.71, N 6.22.
1-(2,6-Dimethylpyridin-3-yl)ethanone (6d)
Rf 0.4 (20% EtOAc in petroleum ether). IR (neat, cm–1):
1
1686. H NMR (400 MHz, CDCl3) δ: 2.57 (s, 3H), 2.73 (s,
3H), 7.05–7.07 (s, 1H, J = 8 Hz), 8.08–8.10 (s, 1H, J =
8 Hz). 13C NMR (100 MHz, CDCl3) δ: 13.6, 24.3, 40.0,
120.8, 124.9, 139.1, 159.1, 161.0, 166.6. MS (EI) m/z (%):
149 (60) [M+]. Anal. calcd. for C9H11NO: C 72.46, H 7.43,
N 9.39; found: C 72.58, H 7.50, N 9.42.
7. (a) M.C. Bagley, J.W. Dale, and J. Bower. Chem. Commun.
(Cambridge), 1682 (2002); (b) X. Xiong, M.C. Bagley, and K.
Chapaneri. Tetrahedron Lett. 45, 6121 (2004); (c) M.C.
Bagley, K. Chapaneri, J.W. Dale, X. Xiong, and J. Bower. J.
Org. Chem. 70, 1389 (2005).
8. (a) T. Welton. Chem. Rev. 99, 2071 (1999); (b) P. Wassercheid
and K. Wilhelm. Angew. Chem. Int. Ed. 39, 3772 (2000);
(c) R. Sheldon. Chem. Commun. 2399 (2001).
1-(2,6-Dimethyl-4-phenylpyridin-3-yl)ethanone (6e)
Rf 0.34 (20% EtOAc in petroleum ether). IR (neat, cm–1):
1
1686. H NMR (400 MHz, CDCl3) δ: 2.55 (s, 3H), 2.75 (s,
3H), 7.00 (s, 1H), 7.31–7.39 (m, 5H). 13C NMR (125 MHz,
CDCl3) δ: 23.3, 24.3, 27.7, 121.3, 125.9, 127.9, 128.51,
128.57, 138.7, 148.7, 155.1, 158.6, 169.04. MS (EI) m/z
(%): 225 (60) [M+], 115 (100). Anal. calcd. for C15H15NO:
C 79.97, H 6.71, N 6.22; found: C 80.16, H 6.79, N 6.33.
9. R.S. Varma and V.V. Namboodivi. Chem. Commun. (Cam-
bridge), 543 (2001).
10. J. Howart, K. Hanlon, D. Fayne, and P. McCormac. Tetrahe-
dron Lett. 38, 3097 (1997).
11. (a) A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver,
D.C. Forbes, and J.H. Davis, Jr. J. Am. Chem. Soc. 124, 5962
(2002); (b) H.P. Zhu, F. Yang, J. Tang, and M.Y. He. Green
Chem. 5, 38 (2003).
12. (a) G. Karthikeyan and P.T. Perumal. Synlett, 2249 (2003);
(b) G. Karthikeyan and P.T. Perumal. J. Heterocycl. Chem. 41,
1039 (2004).
Acknowledgement
One of the authors (G.K.) thanks the Council of Scientific
and Industrial Research, New Delhi for the financial support.
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