Abstract
An efficient synthesis of 2,3-diarylated fully substituted furans
was performed through the sequential reactions of Knoevenagel reaction,
Stetter reaction catalyzed by NHC, and intramolecular cyclization
under solvent-free conditions. The protocol has the advantages of
easy workup, high yields, and an environmental benign procedure
compared with the reported methods.
Key words
NHC - fully substituted furans - umpolung - solvent-free synthesis - multicomponent reaction
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21
General Procedure
for the Synthesis of 5
Aryl aldehyde 1 (1
mmol), DBU (0.35 mmol), and malononitrile 2 (1
mmol) were triturated together in an agate mortar with a pestle
for 5 min. Then the mixture was kept at 55 ˚C for a certain
time (monitored by TLC). After addition of another aryl aldehyde
(1 mmol), sulfamethiazole salt (0.15 mmol) was added and mixed thoroughly
by grinding at 55 ˚C. The reaction mixture was mixed by
grinding every half an hour with a pestle and mortar during 1-5
h reaction time (monitored by TLC). The resultant mixture was cooled to
r.t., purified through column chromatography using acetone and PE
(1:5) as the eluent, to give pure product 5a -o .
22
Characterization
Data of Representative Compounds 5a
max = 3467,
3443, 2216, 1653, 1455, 1067, 763, 694 cm-¹ . ¹ H
NMR (400 MHz, DMSO-d
6 ): δ = 7.17-7.27
(m, 5 H, ArH), 7.38-7.47 (m, 5 H, ArH). 7.75 (s, 2 H, NH2 )
ppm. ¹³ C NMR (100 MHz, DMSO-d
6 ): δ = 163.5, 136.6,
131.2, 129.4, 129.0, 128.8, 128.6, 128.3, 126.9, 124.2, 121.8, 115.5,
69.2 ppm. ESI-HRMS: m/z calcd
for C17 H11 N2 O [M - H]- :
259.0871; found: 259.0871.
