References and Notes
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Crystallographic data (excluding structure
factors) of compound 8 have been deposited
with the Cambridge Crystallographic Data Centre as supplementary
publication number CCDC-665160. These data can be obtained free
of charge via www.ccdc.cam.ac.uk/data_request/cif
or by emailing data_request@ccdc.cam.ac.uk or
by contacting The Cambridge Crystallographic Data Centre, 12, Union Road,
Cambridge CB2 1EZ, UK; fax: +44 (1223)336033.
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Procedure for the
Preparation of 13
To a solution of 12 (500
mg, 2.06 mmol) in DCE (10 mL) was added 4-hydroxy-7-N,N-dimethylaminocoumarin
(423 mg, 2.06 mmol) and a catalytic amount of PTSA. After the mixture
was stirred at 50 ˚C for 6 h, H2O (5 mL) was
added to the mixture and the product was extracted twice with CH2Cl2.
The combined organic extracts were dried over anhyd MgSO4,
filtered, and concentrated. The resulting crude product was purified
by column chromatography (EtOAc-hexane, 7:15) to give a
blue solid with a 35% yield; mp 258-259 ˚C. ¹H
NMR (300 MHz, CDCl3): δ = 9.62
(s, 1 H), 8.34 (dd, J = 8.4,
1.2 Hz, 1 H), 7.98 (d, J = 8.7
Hz, 1 H), 7.90 (dd, J = 8.1,
1.2 Hz, 1 H), 7.87-7.84 (m, 2 H), 7.74 (ddd, J = 8.1, 7.2,
1.2 Hz, 1 H), 7.63-7.52 (m, 4 H), 6.60 (dd, J = 9.0, 2.4
Hz, 1 H), 6.42 (d, J = 2.4
Hz, 1 H), 3.09 (s, 6 H). ¹³C NMR (75
MHz, CDCl3): δ = 176.9,
165.1, 164.2, 156.48, 156.47, 155.9, 154.5, 139.1, 136.2, 134.9,
132.2, 131.8, 129.8, 129.7, 128.2, 128.0, 127.8, 126.6, 110.7, 108.4,
108.1, 97.3, 40.2. IR (KBr): ν = 1674,
1615, 1488, 1205 cm-¹. HRMS (EI): m/z calcd for C26H19NSO3: 425.1086;
found: 425.1081 [M+].
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4831
