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14
Experimental Procedure
for the Synthesis of Spiroben-zofuranol 3 and 4:
A
mixture of salicylaldehyde 1 (1.62 mmol,
1.2 equiv),
N-substituted maleimide 2 (1.35
mmol, 1.0 equiv) and DABCO (30 mol%) was stirred at 70 ˚C
under neat conditions for 1-2 h. The residue was dissolved
in EtOAc (20 mL) and given a dilute HCl wash (1 × 20 mL)
and H2O wash (2 × 20 mL). The EtOAc layer was
dried over anhyd Na2SO4 and removal of solvent
under reduced pressure gave a crude product, which was purified
by flash column chromatography with EtOAc-PE (20:80) as
eluent to obtain spirobenzofuranols 3 and 4.
Spectral
Data of Compound 3b: colorless solid; mp 162-164 ˚C; R
f
0.33
(50% EtOAc-PE). IR: 3450, 2918, 1785, 1698, 1623,
1441, 1195 cm-¹. ¹H
NMR (500 MHz, DMSO-d
6): δ = 1.26
(t, 3 H, J = 6.9 Hz), 2.85 (s,
3 H), 2.88 (d, 1 H, J = 18.3
Hz), 3.37 (d, 1 H, J = 18.3
Hz), 3.98-4.03 (m, 2 H), 5.19 (d, 1 H, J = 6.9
Hz), 6.17 (d, 1 H, J = 6.9 Hz),
6.87-6.95 (m, 3 H). ¹³C NMR
(125 MHz, DMSO-d
6): δ = 15.1,
25.1, 35.0, 64.3, 73.8, 89.6, 114.5, 117.9, 122.6, 129.9, 143.7, 147.4,
174.3, 176.2. HRMS: m/z calcd for C14H15NO5: 277.0952;
found: 277.0957.
15 Crystallographic data of the compound 3a in this paper have been deposited with
the Cambridge Crystallographic Data Centre as supplemental publication
no. CCDC-724171. Copies of the data can be obtained, free of charge
on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44
(1223)336033 or email: deposit@ccdc.cam.ac.uk].
17
Experimental Procedure
for the Synthesis of Spiroben-zofuranone 9:
A mixture
of salicylaldehyde 1 (1.62 mmol, 1.2 equiv),
N-substituted
maleimide 2 (1.35 mmol, 1.0 equiv) and DABCO
(30 mol%) was stirred under neat conditions at 70 ˚C
for 1-2 h. After the formation of spirobenzofuranols 3 and 4, CH2Cl2 and
PDC (1.2 equiv) were added to the reaction mixture and the mixture
was refluxed. After 1 h the reaction mixture was filtered on a celite
pad. The filtrate was concentrated, poured into H2O,
and extracted with EtOAc (3 × 20 mL). The organic layer
was dried over anhyd Na2SO4 and removal of
solvent under reduced pressure gave a crude product, which was purified
by column chromatography with EtOAc-PE (10:90) as eluent
to obtain the spirobenzofuranone 9.
Spectral Data of Compound 9b:
colorless solid; mp 136-138 ˚C; R
f
0.46 (40% EtOAc-PE).
IR: 2930, 1715, 1602, 1383, 1159 cm-¹. ¹H
NMR (500 MHz, CDCl3): δ = 1.47 (t,
3 H, J = 6.9 Hz), 3.06 (s, 3
H), 3.13 (d, 1 H, J = 18.4 Hz),
3.20 (d, 1 H, J = 17.6 Hz),
4.16 (q, 2 H, J = 6.9 Hz), 7.08
(t, 1 H, J = 7.6 Hz), 7.17 (d,
1 H, J = 8.4 Hz), 7.24 (t, 1
H, J = 7.6 Hz). ¹³C
NMR (125 MHz, CDCl3): δ = 14.8, 25.9,
37.4, 65.0, 86.9, 115.9, 120.4, 120.8, 124.2, 145.9, 163.1, 170.3,
172.5, 196.2. MS: m/z = 276 [M+ + 1].
Anal. Calcd for C14H13NO5 (275.06):
C, 61.09; H, 4.76; N, 5.09. Found: C, 61.17; H, 4.78; N, 5.01.