(E)-2-(3-Fluorobenzylidene)-1,4-diphenylbut-3-yn-1-one (1c)
Yellow solid. Mp: 60–62 °C.
1H NMR (400 MHz, CDCl3): δ 8.12–8.09 (m, 1H), 8.05 (d, J = 7.6 Hz, 2H), 7.52 (d, J = 7.6 Hz, 1H), 7.65–7.61 (m, 2H), 7.53 (t, J = 7.6 Hz, 2H), 7.48–7.41 (m, 3H), 7.38–7.35 (m, 3H), 7.19–7.15 (m, 1H).
13C NMR (100 MHz, CDCl3): δ 193.0, 162.7 (J = 244.4 Hz), 143.1 (J = 2.8 Hz), 137.0, 136.9, 136.8, 132.8, 131.4, 130.1, 130.0, 129.8, 129.1, 128.5, 128.2, 126.7 (J = 2.7 Hz), 122.3 (J = 42.2 Hz), 117.4 (J = 21.5 Hz), 116.1 (J= 22.7 Hz), 102.0, 86.8.
IR (KBr): 3053, 2192, 1660, 1589, 1496, 1441, 1277, 1222, 1145, 986, 904, 778, 756, 718 cm–1.
LC–MS: m/z 327 [M + 1]+. Anal. Calcd for C23H15FO: C, 84.64; H, 4.63. Found: C, 84.52; H, 4.68.
Gold-Catalyzed Concomitant [3 + 3] Cycloaddition/Cascade Heterocyclization of Enynones/Enynals with Azides Leading to Furanotriazines
School of Chemistry, University of Hyderabad, Hyderabad 500 046, Telangana, India
J. Org. Chem., Article ASAP
DOI: 10.1021/acs.joc.5b02567
Publication Date (Web): January 15, 2016
Copyright © 2016 American Chemical Society
Abstract
[Au]-catalyzed
[3 + 3] cycloaddition reaction of enynones/enynals with azides, which
allows the efficient regioselective synthesis of highly fused furo[3,4-d][1,2,3]triazines
in good-to-excellent yields under mild conditions, has been developed.
The synthetic utility of furanotriazines was exploited by oxidation with
cerium ammonium nitrate (CAN) affording highly functionalized
dihydrotriazines. Both furo[3,4-d][1,2,3]triazines and dihydrotriazines exhibit good fluorescence activity.
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