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DOI: 10.1055/s-0030-1258571
Palladium-Catalyzed, Microwave-Enhanced Three-Component Synthesis of Isoquinolines with Aqueous Ammonia
Publikationsverlauf
Publikationsdatum:
23. September 2010 (online)
Abstract
A variety of substituted isoquinoline derivatives can be synthesized in moderate yield by a palladium-catalyzed, microwave-assisted MCR starting from o-bromoarylaldehydes, terminal alkynes, and aqueous ammonia.
Key words
multicomponent reaction - alkynes - aqueous ammonia - isoquinoline - palladium
- 1a
Multicomponent
Reactions
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References and Notes
Synthesis of 3-(4-Methoxyphenyl)isoquinoline
(3d)
In a sealed MW test tube, to a solution of 2-bromobenz-aldehyde
(1a, 185 mg, 0.116 mL, 1 mmol) in THF (1
mL), 4-ethynylanisole (159 mg, 0.156 mL, 1.2 mmol), and trans-dichlorobis(triphenylphosphine)palladium
(7.02 mg, 0.01 mmol) were added. The solution was stirred at r.t.
for 10 min, then NH3 (2.5 M aq, 3 mL) and CuI (3.81 mg,
0.02 mmol) were added. The stirred reaction mixture was heated at
130 ˚C (max. power setting = 500
W) in a multimode microwave oven (Microsinth Milestone®)
for 2 h. The reaction mixture was diluted with H2O (70
mL) and extracted with EtOAc (3 × 70
mL). The organic layer dried with Na2SO4,
was evaporated to dryness, and the crude material was purified by
flash chromatography over a silica gel column (hexane-EtOAc = 96:4)
yielding the isoquinoline 3d (132 mg, 56%)
as brown solid; mp 85-87 ˚C. IR (KBr):
1626, 1606, 1584, 1512, 1447, 1292, 1249, 1179, 1024, 834 cm-¹. ¹H
NMR (200 MHz, CDCl3): δ = 3.88 (s,
3 H, CH3), 7.04 (d, 2 H, arom, J = 8.8
Hz), 7.57 (ddd, 1 H, arom, J = 8.1,
7.0, 1.1 Hz), 7.67 (ddd, 1 H, arom, J = 8.4, 7.0,
1.5 Hz), 7.85 (d, 1 H, arom, J = 8.1
Hz), 7.95-7.99 (m, 2 H, arom), 8.08 (d, 2 H, arom, J = 8.8 Hz),
9.31 (s, 1 H, arom). ¹³C NMR (50.3
MHz, CDCl3): δ = 55.6
(CH3), 114.5, 115.5, 126.8, 126.9, 127.8, 128.4, 130.6,
152.5 (CH arom), 127.7, 132.6, 137.0, 151.4, 160.5 (C quat.). ESI-MS: m/z (%) = 236
(100) [M + 1]+. Anal.
Calcd for C16H13NO (235.28): C, 81.68; H,
5.57; N, 5.95. Found: C, 81.77; H, 5.60; N, 5.93.