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General Procedure
for the Synthesis of Phenyl Propiolamides 2a-j
N
-(1-Ethyl-2-oxo-1,2-dihydroquinolin-6-yl)-
N
-methyl-3-phenylpropiolamide
(2e)
A mixture of phenylpropiolic acid (500 mg, 3.42
mmol) and SOCl2 was stirred at 100 ˚C
for 1.5 h. After evaporation of the solvent, the residue was dissolved
in CH2Cl2 (20 mL). A solution of amine 1e (691 mg, 3.42 mmol) in CH2Cl2 (20 mL)
and TBAHS (cat. amount) was added to the stirred solution of acid
chloride. To this reaction mixture an aq solution of K2CO3 (930
mg, 6.84 mmol) was added slowly. After stirring for 6 h at r.t.,
the solution was washed with 5% HCl (2 × 20
mL) and then with 5% aq NaOH (2 × 20
mL). The organic layer was dried (Na2SO4),
and the solvent was evaporated under reduced pressure. The residue
was purified by column chromatography over silica gel using EtOAc-PE (3:7)
as an eluent to afford amide 2e. Other
compounds 2a-d,f-j were
also prepared accordingly.
White solid; mp 116-118 ˚C;
yield 87%. IR (KBr): 2216, 1643, 1591 cm-¹. ¹H
NMR (400 MHz, CDCl3): δ = 1.39
(t, 3 H, J = 7.2
Hz), 3.43 (s, 3 H), 4.36-4.43 (m, 2 H), 6.77 (d, 1 H, J = 9.2 Hz),
7.09 (d, 2 H, J = 7.2
Hz), 7.21 (t, 2 H, J = 7.6 Hz),
7.32 (t, 1 H, J = 7.2
Hz), 7.45 (d, 2 H, J = 8.4
Hz), 7.59 (s, 1 H), 7.68 (d, 1 H, J = 9.2
Hz). ¹³C NMR (100 MHz, CDCl3): δ = 161.7,
154.3, 138.3, 138.2, 137.2, 132.3, 130.2, 129.7, 128.6, 128.4, 127.3,
123.0, 121.2, 120.1, 114.8, 91.4, 82.5, 37.6, 36.5, 12.7. HRMS (ESI+): m/z [M + H+] calcd
for C21H18N2O2: 331.1441;
found: 331.1440.
<A NAME="RB13711ST-20">20</A>
General Procedure
for the Synthesis of Spiro Compounds 3a-jProcedure
for the Synthesis of 1′-Ethyl-4-iodo-5′-methoxy-1-methyl-3-phenyl-1′
H
-spiro[pyrrole-2,6′-quinoline]-2′,5
(1
H
,5′
H
)-dione (3e)
Using
the general procedure, compound 2e (150
mg, 0.45 mmol), NaHCO3 (115 mg, 1.36 mmol), and molecular
I2 (346 mg, 1.36 mmol) were added in MeCN (5 mL) containing
MeOH (1.5 equiv) and stirred at r.t. for 4.2 h. Then the reaction
mixture was quenched similarly with 10% Na2S2O3 solution,
extracted with CH2Cl2 (3 × 15
mL), washed with H2O (2 × 10
mL) followed by brine (10 mL), and dried over anhyd Na2SO4.
The solvent was removed to give a crude mass which was purified
by column chromatography over silica gel (230-400 mesh)
using EtOAc-PE (1:1) as eluent to furnish the desired product 3e. Other compounds 3a-d,f-j were also prepared accordingly.
Yellow
solid; mp 184-186 ˚C; yield: 90%.
IR (KBr): 1695, 1652, 1621 cm-¹. ¹H
NMR (400 MHz, CDCl3): δ = 1.28
(t, 3 H, J = 7.2
Hz), 2.91 (s, 3 H), 3.34 (s, 3 H), 4.13-4.19 (m, 2 H),
4.28 (s, 1 H), 6.01 (d, 1 H, J = 10.0
Hz), 6.45 (d, 1 H, J = 9.2
Hz), 6.92 (d, 1 H, J = 10.4
Hz), 7.22 (d, 1 H, J = 9.6 Hz),
7.37-7.42 (m, 5 H). ¹³C NMR
(100 MHz, CDCl3): δ = 167.0,
161.6, 161.4, 137.2, 136.6, 132.9, 130.4, 129.7, 128.7, 128.7, 123.5,
119.7, 114.0, 78.5, 72.4, 59.9, 38.3, 28.5, 14.5. HRMS (ESI+): m/z [M + Na+] calcd
for C22H21IN2O3: 511.0489;
found: 511.0441.
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