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DOI: 10.1055/s-0029-1219565
Microwave-Assisted Preparation of Quinolone and Quinoline Derivatives
Publication History
Publication Date:
02 March 2010 (online)
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Abstract
Quinolinone derivatives can be obtained in microwave-assisted syntheses by reaction of aniline derivatives with acetylene dicarboxylic esters, a malonic acid diester or β-keto ester derivatives. The reaction proceeds under mild conditions in short reaction times. Two of the quinolinones were transformed into the corresponding 4-chloroquinolines either by conventional heating or in a microwave-assisted reaction. Further modifications resulted in the formation of the boron adduct or in an agglomerate. The latter was characterized by X-ray crystal structure analysis.
Key words
quinoline - quinolinone - one-pot synthesis - microwave
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References and Notes
Microwave experiments were performed
using a CEM Discover BenchMate Plus microwave oven with IR temperature
detection. Preparation of
4: O-Anisidine
(0.123 g, 1.0 mmol), dimethyl acetylenedicarboxylate (0.156 g, 1.1 mmol)
and Ph2O (6 mL) were placed in a 10 mL vessel, which
was sealed with a septum. The flask was placed in the MW cavity
and was locked with the pressure device. MW irradiation at 120 ˚C
without air-cooling was used during the first 5 min of reaction
time, and then irradiation power was increased to 250 ˚C
for the next 15 min. After cooling to r.t., the reaction mixture
was diluted with n-hexane (150 mL).
A
brown oil or solid precipitated. Solvent was removed and the residue
was washed with n-hexane and recrystallized from
acetone-n-hexane to yield a
colourless crystalline solid in 54% yield. Characterization
of key products: The analytical data of 4,¹² 7
¹³ and 20
¹³ were
in agreement with literature data. Derivative 19:
Mp 146 ˚C. ¹H NMR (400 MHz,
CDCl3): δ = 8.32 (s, 1 H),
7.84 (dd, J = 8.5,
1.1 Hz, 1 H), 7.68 (dd, J = 8.5,
8.0 Hz, 1 H), 7.15 (dd, J = 8.0,
1.1 Hz, 1 H), 4.10 (s, 3 H), 4.05 (s, 3 H). ¹³C
NMR (75 MHz, CDCl3): δ = 165.0 (C),
156.1 (C), 146.1 (C), 143.7 (C), 140.1 (C), 130.1 (CH), 128.6 (C),
121.8 (CH), 115.4 (CH), 108.9 (CH), 56.3 (CH3), 53.2
(CH3). MS (EI, 70 eV): m/z (%) = 251.0(36) [M]+,
235.9 (100) [M - Me]+.
IR (KBr): 3094, 1721, 1611, 1557, 1498, 1470, 1448, 1334, 1259, 1204,
1139, 1108, 1009, 969, 896, 819, 784, 747 cm-¹.
Anal. Calcd for C12H10ClNO3˙1/3H2O
(257.7): C, 55.94; H, 4.17; N, 5.44. Found: C, 55.70; H, 4.10; N,
5.56.
CCDC 761359 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033, E-mail: deposit@ccdc.cam.ac.uk].