- Copper(II)-Promoted, One-Pot Conversion of 1-Alkynes with Anhydrides or Primary Amines to the Respective 2,5-Disubstituted Furans or Pyrroles under Microwave Irradiation Conditions
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Furans and pyrroles are prepared from 1-alkynes by using a Cu(II)-promoted, one-pot, microwave irradiation method. Glaser coupling of 1-alkynes and cyclization of the resulting 1,3-diyne in the presence of an anhydride or a primary amine results in the formation of the respective 2,5-diaryl- or 2,5-dialkyl-substituted furans and pyrroles.
- Lee, Hyejeong,Yi, Yeonhui,Jun, Chul-Ho
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supporting information
p. 3485 - 3490
(2016/01/25)
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- The Diels-Alder Reaction of 2,5-Dialkylfurans and Fumaronitrile Revisited
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The equilibrium reactions of furan and 2,5-dialkyl derivatives with fumaronitrile were investigated under standard conditions (3.0*10-4M) at four different temperatures in chloroform-d as solvent.Plots of lnK against 1/T were linear for each member of the series.The results show that the equilibrium concentration of adduct is sensitive to substituents.At equilibrium, there is a greater proportion of adduct derived from 2,5-dimethylfuran than from furan itself.However, as the length of the substituent chains is increased, the proportion of adduct decreases.Similar trends are also apparent from a more limited study of the equilibria in methanol-d4 and acetone-d6 as solvents.The concentrations of adduct in the equilibrium mixtures are highest in chloroform-d and lowest in acetone-d6.AM1 calculations are reported for model adduct structures.
- Cook, Michael J.,Cracknell, Steven J.
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p. 12125 - 12132
(2007/10/02)
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