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PAPER
Table 3 Selected 1H and 13 C NMR Spectral Data of Products
Product 1H NMR (DMSO-d6, TMS), d
13 C NMR (DMSO-d6, TMS), d
1
0.92 (t, J = 6.6 Hz, 3 H, 6¢-H), 1.30–1.46 (m, 6 H, 2¢-H, 3¢-H, 4¢-H), 1.54–1.66 14.7, 27.4, 30.2, 32.4, 44.7, 63.8, 120.5, 124.0, 128.6,
(m, 2 H, 5¢-H), 3.08 (t, J = 6.9 Hz, 2 H, 1¢-H), 3.56 (br s, 1 H, NH exch. D2O), 140.7
7.08–7.59 (m, 5 Harom
)
2
0.91 (t, J = 6.6 Hz, 3 H, 6¢-H), 1.29–1.50 (m, 6 H, 2¢-H, 3¢-H, 4¢-H), 1.56–1.66 14.5, 21.1, 27.2, 29.9, 32.5, 44.6, 63.5, 120.3, 124.3,
(m, 2 H, 5¢-H), 2.31 (s, 3 H, Me) 3.10 (t, J = 6.9 Hz, 2 H, 1¢-H), 3.55 (br s, 1 133.6, 138.0
H, NH exch. D2O), 7.09–7.60 (m, 4 Harom
)
10
2.04 (s, 3 H, COMe), 2.32 (s, 3 H, Me), 8.04 (br s, 1 H, NH, exch. D2O), 7.10– 17.7, 21.0, 120.2, 129.5, 133.3, 137.7, 168.3
7.58 (m, 4 Harom
2.75 (s, 4 H, CH2CH2), 7.04–7.68 (m, 5 Harom
2.37 (s, 3 H, Me), 7.08–8.10 (m, 8 Harom
)
13
16
)
26.2, 120.3, 124.1, 128.6, 140.9, 173.8
)
20.9, 120.2, 127.5, 129.4, 131.4, 132.5, 133.2, 135.3,
166.5
17
19
21
2.71 (dd, J = 13.0, 15.5 Hz, 1 H, COCH2), 3.03 (dd, J = 2.5, 15.5 Hz, 1 H,
32.5, 43.2, 47.6, 120.5, 124.0, 128.6, 129.2, 133.2,
COCH2), 3.05 (dd, J = 4.5, 15.5 Hz, 1 H, NCOCH2), 3.49 (dd, J = 5.0, 15.5 141.0, 169.8, 197.7
Hz, 1 H, NCOCH2), 4.25 (m, 1 H, NCH), 7.07–7.91 (m, 4 Harom
)
3.38 (dd, J = 5.5, 16.0 Hz, 1 H, NCOCH2), 3.97 (dd, J = 2.8, 16.0 Hz, 1 H,
NCOCH2), 4.75 (dd, J = 2.8, 5.5 Hz, 1 H, NCH), 5.12 (s, 4 H, OCH2), 6.08– 128.4, 129.0, 129.6, 133.3, 140.6, 141.2, 169.9,
7.91 (m, 14 Harom 171.9, 197.8
32.4, 43.8, 72.3, 79.1, 120.4, 124.2, 127.1, 127.7,
)
1.80 (ddd, J = 2.75, 12.5, 14.0, 1 H, CH2), 2.1 (s, 3 H, Me), 2.57 (ddd, J = 3.0, 17.6, 32.3, 40.9, 43.4, 51.0, 72.5, 120.2, 124.0, 128.6,
3.0, 14.0, 1 H, CH2), 2.99 (dd, J = 2.5, 15.5 Hz, 1 H, NCOCH2), 3.7 (dd, J = 129.4, 133.8, 141.1, 165.6, 171.3, 172.3
5.0, 15.5 Hz, 1 H, NCOCH2), 3.97 (s, 3 H, Me), 4.19 (m, 1 H, NCH), 6.19 (dd,
J = 2.75, 3.0 Hz, 1 H, OCH) 7.55–8.02 (m, 3 Harom
)
24
2.67 (dd, J = 3.5, 17.0 Hz, 1 H, NCOCH2), 3.43 (dd, J = 6.0, 17.0 Hz, 1 H,
NCOCH2), 4.36 (m, 1 H, NCH), 5.14 (s, 4 H, OCH2), 7.2.0–7.78 (m, 14 Harom
32.1, 44.2, 67.8, 72.1, 120.5, 121.3, 124.0, 125.5,
) 126.2, 128.2, 129.0, 130.4, 140.6, 153.2, 169.7, 171.8
(17) Strohmeier, G. A.; Kappe, C. O. J. Comb. Chem. 2002, 4,
154.
(18) Alexandre, F. R.; Domon, L.; Frere, S.; Testard, A.; Thiery,
V.; Besson, T. Mol. Diversity 2003, 7, 273.
Acknowledgment
We sincerely thank SAIF, Punjab University, Chandigarh, for pro-
viding microanalyses and spectra.
(19) Varma, R. S. J. Heterocycl. Chem. 1999, 36, 1565.
(20) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002,
35, 717.
References
(21) Hayes, B. L. In Microwave Technology Chemistry at the
Speed of Light; CEM Publishing: Mathews NC, 2002, 29.
(22) Varma, R. S. In Microwave Technology Chemical
Applications: Kirk–Othmer Encyclopedia of Chemical
Technology, 5th ed.; John Wiley & Sons: New York, 2004.
(23) Li, J.; Chan, T. H. Organic Reaction in Aqueous Media; John
Wiley & Sons: New York, 1997.
(1) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
(2) Lindley, J. Tetrahedron 1984, 40, 1433.
(3) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemairc, M.
Chem. Rev. 2002, 102, 1359.
(4) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046.
(5) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999,
576, 125.
(24) Grieco, A. P. Organic Synthesis in Water; Blackie Academic
(6) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219,
131.
and Professional: London, 1998.
(25) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
(26) Wei, W.; Keh, C. C. K.; Li, C. J.; Varma, R. S. Clean Tech.
Environ. Policy 2005, 7, 62.
(27) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.
(28) An, J.; Bagnell, L.; Cablewski, T.; Strauss, C. R.; Trainor, R.
W. J. Org. Chem. 1997, 62, 2505.
(29) Strauss, C. R. Aust. J. Chem. 1999, 52, 83.
(30) Ju, Y.; Varma, R. S. Green Chem. 2004, 6, 219.
(31) Dandia, A.; Arya, K.; Sati, M. Synth. Commun. 2004, 34,
1141.
(32) Ju, Y.; Varma, R. S. Org. Lett. 2005, 7, 2409.
(33) Yadav, L. D. S.; Kapoor, R. J. Org. Chem. 2004, 69, 8118.
(34) Yadav, L. D. S.; Singh, A. Tetrahedron Lett. 2003, 44, 5667.
(35) Yadav, L. D. S.; Singh, S. Synthesis 2003, 63.
(36) Yadav, L. D. S.; Yadav, S.; Rai, V. K. Tetrahedron 2005, 61,
10013.
(7) Oida, S.; Yashida, A.; Hayashi, T.; Naikayama, E.; Sato, S.;
Okhi, E. Tetrahedron Lett. 1980, 21, 619.
(8) McCombie, S. W.; Ganguly, A. K.; Girijavallabhan, V. M.;
Jeffrey, P. D.; Lin, S.; Pinto, P.; McPhail, A. T. Tetrahedron
Lett. 1981, 22, 3489.
(9) Joyeau, R.; Dugenet, Y.; Wakselman, M. J. Chem. Soc.,
Chem. Commun. 1983, 431.
(10) Joyeau, R.; Yadav, L. D. S.; Wakselman, M. J. Chem. Soc.,
Perkin Trans. 1 1987, 1899.
(11) Yamamoto, T.; Kurata, Y. Chem. Ind. (London) 1981, 737.
(12) Yamamoto, T.; Kurata, Y. Can. J. Chem. 1983, 61, 86.
(13) Varma, R. S. Green Chem. 1999, 1, 43.
(14) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
(15) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J.
Tetrahedron 2001, 57, 9225.
(16) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250.
(37) Gore, P. H.; Hughes, G. K. J. Chem. Soc. 1959, 1615.
Synthesis 2006, No. 11, 1868–1872 © Thieme Stuttgart · New York