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General Procedure
for the Synthesis of Compound 3a by Heck Reaction
A
mixture of 1a (100 mg, 0.395 mmol), cyclohexanone
(2a, 77.5 mg, 0.79 mmol), and DABCO (132.7
mg, 1.185 mmol) was taken in DMF (5 mL) under nitrogen atmosphere. Pd(OAc)2 (10
mol%, 8.8 mg) was added and the reaction mixture was stirred
at 120 ˚C for 4 h. After completion of the reaction
as monitored by TLC, the reaction mixture was cooled, H2O
(20 mL) was added and extracted with EtOAc (3 × 30
mL). The EtOAc extract was washed with H2O (2 × 40
mL), followed by brine (30 mL). The organic layer was dried (Na2SO4),
and the solvent was evaporated to give a crude product which was
purified by column chromatog-raphy over silica gel (230-400
mesh) using PE-EtOAc (3:2) as eluent. Product 3a was isolated as a white solid in 91% yield.
Compound 3a
Yield 91%,
solid, mp 254-256 ˚C. IR (KBr): 1637,
3305 cm-¹. ¹H NMR
(400 MHz, CDCl3): δ = 8.30
(d, 1 H, J = 9.5 Hz),
8.00 (s, 1 H), 7.48 (d, 1 H, J = 9.0
Hz), 7.13 (d, 1 H, J = 9.0
Hz), 6.73 (d, 1 H, J = 9.5
Hz), 3.80 (s, 3 H), 3.00 (br s, 2 H), 2.80 (br s, 2 H), 1.93 (br
s, 4 H). ¹³C NMR (100 MHz, DMSO): δ = 22.17,
23.13, 23.18, 23.41, 29.57, 107.28, 108.69, 112.51, 114.75, 118.38,
122.47, 130.57, 134.79, 135.60, 136.82, 160.65; MS: m/z = 253 [M+ + H].
Anal. Calcd for C16H16N2O: C, 76.16;
H, 6.39; N, 11.10. Found: C, 76.34, H, 6.42, N, 11.27.
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