1 - Memorial University of Newfoundland
1 - Memorial University of Newfoundland
1 - Memorial University of Newfoundland
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while solid (0.1 J. 78%). mp = 273-274 °C; o..(DMSQ-d,) = 7.68 (dd. j = 7.2, 2.6 Hz, IH.<br />
H-3). 7.40-7.37 (m. 3H), 7.34-7.30 (m. 4H), 7.24 (m. IH). 7.22-7.21 (m. Ifl), 7.19 (dd. j<br />
= 7.8. 2.8 Hz. IH). 6.68 (d. j = 8.4 Hz, IH. H-II). 6.08 (s. IH. H-7),4.42 (d. j = 10.2 Hz.<br />
IH. H-7a). 4.29-4.04 (m. 3H), 2.13-2.05 (m. IH, H-13a) ppm: lic(CD,Cl,) =159.1 (C-6).<br />
154.5.150.4.149.2.147.9.131.6.130.0.129.7.127.2. 125.6. 125.0. 124.8. 124.4, 121.6,<br />
121.3 (C-9). 120.4, 119.6, 117.5. 117.2 (C-II), 66.7 (l3). 52.1 (C-7a). 44.9 (C-14). 44.0<br />
(C-13a) ppm; IR v= 3392 (w), 1703 (s). 1620 (m). 1595 (w). 1583 (w). 1559 (w), 1488<br />
(s). 1458 (m), 1410 (m), 1343 (s), 1310 (m). 1275 (m). 1254 (w). 1230 (w). 1217 (m),<br />
1201 (s). 1137 (w). 1077 (m). 1048 (s), 1024 (m). 1009 (m) em"; HRMS 1M·) ealed for<br />
C 25H I 8 OJBr 459.0470, found 459.0468.<br />
(7aR*, 13aR., 14S*)-2-Nitro·14-phcnyl·5,6,7,7a,12,13,13a,14-oclah)'dro·5.12-dioxa<br />
7-azadibcnzo[a,Jt]anthraccn-6-one (64)<br />
According (0 general procedure 3-A, 3·amino-6-nitrocoumarin (0.062 g. 0.30<br />
mlllol), enal45 (0.075 g, 0.32 mmol) and Yb(OTl)) (0.019 g. 1011101%) afforded 64 as a<br />
pale yellow solid (0.105 g. 82%). mp = 262-263 °C; ",,(CD,CI,) = 8.00 (dd, j = 9.0 Hz,<br />
250
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