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DOI: 10.1055/s-0030-1260305
Synthesis of Aminoindolizine and Quinoline Derivatives via Fe(acac)3/TBAOH-Catalyzed Sequential Cross-Coupling-Cycloisomerization Reactions
Publikationsverlauf
Publikationsdatum:
13. September 2011 (online)
Abstract
Fe(acac)3/TBAOH-catalyzed three-component coupling-cycloisomerization reaction of aldehydes, terminal alkynes, and amines provides a diverse range of heterocyclic compounds such as aminoindolizines and quinoline derivatives.
Key word
aminoindolizines - quinoline derivatives - tetrabutylammonium hydroxide (TBAOH) - Fe(acac)3 catalyst - cross-coupling - cycloisomerization
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References and Notes
General Procedure
for the Synthesis of Aminoindolizine Derivatives
To
a solution of TBAOH (0.1 mmol) in DMSO (5 mL), pyridine-2-carboxaldehyde
(1.0 mmol), phenyl acetylene (1.2 mmol), morpholine (1.2 mmol),
and Fe(acac)3 (0.05 mmol) were added successively. The
resulting mixture was stirred at r.t. until the reaction was complete
as indicated by TLC. The mixture was then diluted with EtOAc (5
mL), washed with H2O (2 × 5
mL), and the aqueous phase was extracted with EtOAc (3 × 5
mL). The combined organic phases were washed with sat. aq NaCl,
dried over anhyd Na2SO4, filtered, and concentrated
under vacuum. The residue was purified by flash chromatography on
Al2O3 to afford the target product as a yellow
oil.
4
-
(Methoxyphenyl)-1-(piperidin-1-yl) indolizine
4a
(Table 2,
Product 4b)
Pale yellow liquid. ¹H
NMR (300 MHz, C6D6): δ = 1.40-1.48
(m, 2 H), 1.66-1.74 (m, 4 H), 3.01 (dd, J = 5.4
Hz, 4 H), 3.33 (s, 3 H), 6.04-6.09 (m, 1 H), 6.35 (dd, J = 9.0, 6.3
Hz, 1 H), 6.76 (s, 1 H), 6.78-6.83 (m, 2 H), 7.27-7.32
(m, 2 H), 7.58 (d, J = 9.3
Hz, 1 H), 7.91 (d, J = 7.5
Hz, 1 H). ¹³C NMR (75 MHz, C6D6): δ = 24.8,
27.0, 54.8, 55.7, 106.0, 110.8, 114.0, 114.6, 118.4, 121.6, 122.5,
125.3, 125.6, 129.6, 131.7, 159.0. IR (neat): 2933, 1522, 1245,
1034, 835, 738 cm-¹.
General Procedure
for the Preparation of Quinoline Derivatives
A mixture
of aldehyde (1 mmol) and aniline (1.4 mmol) was dissolved in DMSO
(10 mL) and heated at 60 ˚C for 2 h. It was cooled
to r.t., TBAOH (10 mol%), phenylacetylene (1.2 mmol), and
Fe(acac)3 were added, and the mixture stirred at r.t.
overnight. The reaction mixture was poured into H2O, and
extracted with EtOAc (or CH2Cl2). The organic
layer was washed with H2O and dried over anhyd Na2SO4.
The solvent was removed in vacuo. The product was purified by column
chromatography on silica gel eluting with EtOAc-hexane
(10:90).
4-(4-Methoxyphenyl)-2-(naphthalen-2-yl)quinoline (Table
3, Entry 5)
Pale yellow solid, mp 265-269 ˚C
(lit.¹¹ 268-270 ˚C). ¹H NMR (300 MHz, CDCl3): δ = 3.93
(s, 3 H), 7.10 (d, J = 8.4 Hz,
2 H), 7.26 (s, 1 H), 7.54 (m, 5 H), 7.75 (t, J = 8.1
Hz, 1 H), 7.96 (m, 4 H), 8.28 (d, J = 8.1
Hz, 1 H), 8.41 (d, J = 9
Hz, 1 H), 8.64 (s, 1 H). ¹³C NMR (75
MHz, CDCl3): δ = 55.4. 114.0, 119.4,
125.0, 125.7, 126.6, 127.1, 127.7, 128.5, 128.8, 129.5, 130.0, 130.8,
131.3, 133.4, 136.2, 147.6, 149.8, 156.6, 164.2.