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DOI: 10.1055/s-2008-1072507
Regio- and Chemoselective Unprecedented Imino-Diels-Alder Reactions of 1-Substituted Unactivated Dienes with N-Aryl Imines - Part II [1]
Publikationsverlauf
Publikationsdatum:
17. März 2008 (online)
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Abstract
The chemo- as well as regioselective participation of N-aryl imines as 4π component in aza-Diels-Alder reactions with 3-butadienyl-2-azetidinones in the presence of Lewis acid catalysts resulting in novel quinoline derivatives is described.
Key words
dienyl-2-Azetidinones - imino-Diels-Alder reactions - Lewis acid - regioselectivity - chemoselectivity - quinoline derivatives
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References and Notes
3-[2-(6-Methoxy-2-phenyl-quinolin-4-yl)-vinyl]-1,4-diphenyl-azetidin-2-one (4a): white solid, mp 170-171 °C. 1H NMR (600 MHz, CDCl3): δ = 3.90 (s, 3 H, OCH3), 4.12 (dd, J = 2.3, 7.6 Hz, 1 H, H3), 4.90 (d, J = 2.3 Hz, 1 H, H4), 6.71 (dd, J = 7.6, 15.5 Hz, 1 H, H5), 7.10 (t, J = 6.8 Hz, 1 H, arom.), 7.41 (m, 13 H, arom. and H12), 7.50 (d, J = 15.5 Hz, 1 H, H6), 7.52 (s, 1 H, H14), 7.90 (s 1 H, H8), 8.08 (d, J = 9.2 Hz, 1 H, H11) 8.13 (d, J = 7.4 Hz, 2 H, H18). 13C NMR (75 MHz, CDCl3): δ = 53.4, 61.6, 63.8, 101.4, 115.9, 117.1, 122.0, 124.2, 125.9, 127.2, 128.0, 128.5, 128.7, 128.8, 128.9, 129.1, 129.3, 130.3, 131.7, 137.0, 137.4, 139.7, 141.2, 144.7, 154.8, 157.8, 164.7. MS: m/z = 482 [M]+. IR (KBr): νmax = 1752, 1627, 1565, 1508, 1387 cm-1. Anal. Calcd for C33H26N2O2: C, 82.13; H, 5.43; N, 5.81. Found: C, 82.27; H, 5.58; N, 5.66.