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S. Mukherjee et al.
PAPER
(3) (a) Brown, D. J. Quinoxalines: Supplement II, In The
Coupling of Carbene Complex 27 with {2,6-Dimethoxy-5-[(tri-
methylsilyl)ethynyl]pyrimidin-4-yl}(p-tolyl)methanone (21)
Following general procedure 6 using carbene complex 27 (0.25 g,
0.76 mmol) and 21 (0.22 g, 0.63 mmol); purification of the crude
mixture gave 32 as a gummy solid; yield: 0.17 g (57%); Rf = 0.51
(EtOAc–PE, 1:9).
Chemistry of Heterocyclic Compounds; Taylor, E. C.; Wipf,
P., Eds.; John Wiley & Sons: New Jersey, 2004.
(b) Beifuss, U.; Tietze, M. Top. Curr. Chem. 2005, 244, 77.
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V. Chem. Lett. 2008, 37, 348. (b) Huang, T. K.; Shi, L.;
Wang, R.; Guo, X. Z.; Lu, X. X. Chin. Chem. Lett. 2009, 20,
161. (c) Zhao, Z.; Wisnoski, D. D.; Wolkenberg, S. E.;
Leister, W. H.; Wang, Y.; Lindsley, C. W. Tetrahedron Lett.
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S. S.; Jadhav, W. N.; Bhusare, S. R.; Pawar, R. P.
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Darabantu, M.; Turck, A.; Ple, N. J. Heterocycl. Chem.
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Stephanatou, J.; Tsoleridis, C. A. Synlett 2009, 302.
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5622. (h) Pachter, J.; Kloetzel, M. C. J. Am. Chem. Soc.
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(5) (a) Jiang, D.; Herndon, J. W. Org. Lett. 2000, 2, 1267.
(b) Ghorai, B. K.; Herndon, J. W. Org. Lett. 2001, 3, 3535.
(c) Luo, Y.; Herndon, J. W.; Cervantes-Lee, F. J. Am. Chem.
Soc. 2003, 125, 12720. (d) Ghorai, B. K.; Herndon, J. W.
Organometallics 2003, 22, 3951. (e) Camacho-Davila, A.;
Herndon, J. W. J. Org. Chem. 2006, 71, 6682. (f) Chen, Y.;
Ye, S.; Jiao, L.; Liang, Y.; Sinha-Mahapatra, D. K.;
Herndon, J. W.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129,
10773.
IR (KBr): 3450, 1660, 1576 cm–1
1H NMR (500 MHz, CDCl3): d = 7.09 (d, J = 8.5 Hz, 2 H), 7.06 (d,
J = 8.5 Hz, 2 H), 5.69 (m, 1 H), 4.92 (d, J = 10.0 Hz, 1 H), 4.87 (d,
J = 17.5 Hz, 1 H), 4.04 (s, 3 H), 3.87 (s, 3 H), 2.54–2.44 (m, 2 H),
2.40 (dt, J = 14.0, 6.0 Hz, 1 H), 2.33 (s, 3 H), 2.32 (t, J = 12.5 Hz, 1
H), 2.15 (dd, J = 12.5, 3.0 Hz, 1 H), 1.96 (dt, J = 14.0, 8.0 Hz, 1 H),
1.84–1.73 (m, 3 H, including one OH proton), 0.18 (s, 9 H). Irradi-
ation at d = 5.69: d = 4.92 (s), 4.87 (s), 2.40 (dd), 1.96 (dd); Irradi-
ation at d = 2.32: d = 2.15 (d) and sharpened one multiplet at d =
2.54–2.49; Irradiation at d = 1.96: d = 2.40 (dd) and sharpened the
multiplets at d = 2.49–2.44 and 5.69.
13C NMR (75 MHz, CDCl3): d = 206.2 (s), 169.4 (s), 163.3 (s),
161.5 (s), 159.2 (s), 144.7 (s), 143.7 (s), 137.1 (s), 136.1 (d), 128.8
(d, 2 C), 125.2 (d, 2 C), 116.4 (t), 115.0 (s), 73.8 (s), 55.1 (q), 54.3
(q), 48.0 (t), 43.9 (d), 34.0 (t), 32.7 (t), 31.5 (d), 20.9 (q), 1.91 (q, 3
C).
MS: m/z (%) = 480 (10) [MH+ + 1], 479 (35) [M + H]+, 463 (100)
[M+ – Me].
Anal. Calcd for C27H34N2O4Si: C, 67.75; H, 7.16; N, 5.85. Found:
C, 67.84; H, 7.05; N, 5.91.
(6) (a) Jana, G. P.; Ghorai, B. K. Tetrahedron 2007, 63, 12015.
(b) Jana, G. P.; Ghorai, B. K. Lett. Org. Chem. 2009, 6, 372.
(c) Mukherjee, S.; Jana, G. P.; Ghorai, B. K. J. Organomet.
Chem. 2009, 694, 4100. (d) Jana, G. P.; Mukherjee, S.;
Ghorai, B. K. Synthesis 2010, 3179.
(7) Roy, P.; Ghorai, B. K. Beilstein J. Org. Chem. 2010, 6, No.
52; doi: 10.3762/bjoc.6.52.
(8) For a review on azaisobenzofuran, see: Basak, S.; Ghosh, S.
K.; Sarkar, T. K. J. Indian Inst. Sci. 2001, 81, 431.
(9) Haddadin, M. J.; Yavrouian, A.; Issidorides, C. H.
Tetrahedron Lett. 1970, 11, 1409.
Acknowledgement
Financial support from CSIR [No.01 (2215)/08-EMR-II], Govern-
ment of India is gratefully acknowledged. We thank Professor J. W.
Herndon, Department of Chemistry and Biochemistry, New Mexico
State University, Las Cruces, New Mexico, USA for helpful discus-
sions. We thank CPIPL, Kolkata and IICB, Kolkata for providing
the NMR facility. The UGC and CSIR, New Delhi, are also thanked
for the award of a Senior Research Fellowships to S.M. and P.R.
(10) Butini, S.; Pickering, D. S.; Morelli, E.; Coccone, S. S.;
Trotta, F.; Angelis, M. D.; Guarino, E.; Fiorini, I.; Campiani,
G.; Novellino, E.; Schousboe, A.; Christensen, J. K.;
Gemma, S. J. Med. Chem. 2008, 51, 6614.
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Synthesis 2011, No. 9, 1419–1426 © Thieme Stuttgart · New York