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DOI: 10.1055/s-0030-1261229
A NHC-Involved, Cascade, Metal-Free, and Three-Component Synthesis of 2,3-Diarylated Fully Substituted Furans under Solvent-Free Conditions
Publikationsverlauf
Publikationsdatum:
08. September 2011 (online)
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
- Supporting Information for this article is available online:
- Supporting Information
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0016th:
- Primary Data
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References and Notes
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
Yield 90%,
white solid, mp 205-206 ˚C (reported
204-206 ˚C). IR (KBr): νmax = 3467,
3443, 2216, 1653, 1455, 1067, 763, 694 cm-¹. ¹H
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. ¹³C 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 C17H11N2O [M - H]-:
259.0871; found: 259.0871.