766
Y. Carvajal-Miranda, R. Pérez-Salazar, and J. A. Varela
Vol 53
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Na2SO4 and evaporated to dryness. The residue was purified by
column chromatography eluting with Hex : AcOEt 7:3. H-
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2006, 128, 8087.
1
NMR (300 MHz, CDCl3) δ 8.33 (d, J = 8.3 Hz, 2H), 8.21
(s, 2H), 7.55 (dd, J = 7.7 and 1.6 Hz, 2H), 7.43 (td,
J = 7.7 and 1.6 Hz, 2H), 7.19 (t, J = 7.7 Hz, 2H), 2.99
(s, 2H). 13C-NMR and DEPT (75 MHz, CDCl3) δ 156.90
(2 × C), 149.66 (2 × C), 138.01 (2 × C), 132.14 (2× CH),
130.74 (2 × CH), 124.88 (2 × CH), 120.80 (2 × CH), 111.84
(2 × C), 91.42 (2 × C), 74.96 (2× C). MS (ESI) m/z (%):
233.1 (96), 255.2 (100), 285.0 (44), 311.2 (25).
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58, 6373.
Cycloaddition [2 + 2 + 2].
A mixture of ruthenium-
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catalyzed (0.0112 mmol, 0.1 equiv) compounds, Et4N+ClÀ
(0.0112 mmol, 0.1 equiv), and DMF (1 mL, 0.112 M) was
stirred at rt for 45 min, and 0.063 g (0.1117 mmol) of
diynamide was then added and stirred at rt for 4 h. The
mixture was diluted with diethyl ether, filtered through
silica, and concentrated in vacuo. Purification of the
residue by flash chromatography on silica gel eluting with
1
Hex : EtOAc (7:3) to give 11a was performed. H-NMR
(250MHz, CDCl3) δ 8.61 (s, 2H), 8.53 (m, 3H), 7.67
(d, J= 8.4 Hz, 4H), 7.53 (m, 5H), 7.06 (d, J= 8.4 Hz, 4H),
2.23 (s, 3H). 13C-NMR and DEPT (63 MHz, CDCl3) δ
145.17 (2 × C), 139.06 (2 × C), 136.10 (2 × C), 134.73
(2 × C), 129.78 (4 × CH), 127.51 (2 × CH), 126.60 (4 × CH),
126.13 (2 × C), 123.99 (2 × CH), 123.21 (2 × CH), 121.01
(2 × C), 115.75 (2 × CH), 114.50 (2 × CH), 21.63 (2 × CH3).
MS (ESI) m/z (%): 565.57 (2), 428.11 (22), 427.11 (100).
EMAR (ESI, M+ +1; C32H24N2O4S2) calcd: 565.1250;
found: 565.5657. Mp (°C): 269.6–270.1.
Acknowledgments. We acknowledge Xunta de Galicia and the
European Regional Development Fund for their financial
support. Finally, the authors also thank the support and
general advice from Professor Dr. Carlos Saá.
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Chem 2008, 73, 1320.
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2008, 14, 9772.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet