- Synthesis of 3-alkyl-2,5-dimethylfuran derivatives by indirect alkylation of 2,5-dimethylfuran with aliphatic nitrocompounds
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The preparation of 3-alkyl-2,5-dimethylfuranes via indirect alkylation of 2,5-dimethylfuran is reported. Thus, primary nitroalkanes react with cis-3-hexen-2,5-dione giving a tandem Michael addition/elimination of nitrous acid, followed by chemoselective hydrogenation of the C=C double bond of the obtained enones. The Paal-Knorr reaction, performed with p-toluenesulfonic acid in diethyl ether, completes the formation of the title compounds. In this context the nitroalkane can be considered as an alkyl cation synthon.
- Ballini,Bosica,Fiorini,Giarlo
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p. 2003 - 2006
(2007/10/03)
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- Reactions of acylzirconocene chloride with nucleophiles: Bimodal reactivity at β- and acyl carbons of α,β-unsaturated acylzirconocene chloride
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Reactions of α,β-unsaturated acylzirconocene chloride with nucleophiles showed novel bimodal reactivity at the β- and acyl carbons depending upon the nucleophile employed, and the formation of ketone α,β-dianionic species was also observed. (C) 2000 Elsev
- Hanzawa,Narita,Kaku-uchi,Taguchi
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p. 7525 - 7528
(2007/10/03)
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- 2,5-Dialkylfurans and nitroalkanes as source of 2,3,5-trialkylpyrroles
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The synthesis of 2,3,5-trialkylpyrroles can be easily achieved by conjugate addition of nitroalkanes to 2-alken-1,4-dione (prepared by oxidative cleavage of 2,5-dialkylfuran) in acetonitrile with DBU as base, followed by chemoselective hydrogenation (10% Pd/C as catalyst) of the C-C double bond of the enones obtained by the elimination of nitrous acid from the Michael adduct. The Paal-Knorr reaction, performed on a bed of basic alumina and in the absence of a solvent, completes the formation of the title compounds.
- Ballini, Roberto,Barboni, Luciano,Bosica, Giovanna,Petrini, Marino
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p. 391 - 393
(2007/10/03)
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- A new two-step synthesis of 2-alkylated 1,4-diketones and α-alkylated γ-keto esters
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2-Alkylated 1,4-diketones and α-alkylated γ-keto esters can be easily prepared by a two-step procedure which involves first the conjugate addition of a nitroalkane to an enedione derivative in acetonitrile with DBU as base, followed by chemoselective hydrogenation of the C-C double bond (H2 10% Pd/C) of the Michael adduct, obtained after elimination of nitrous acid.
- Ballini,Bosica,Petrelli,Petrini
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p. 1236 - 1240
(2007/10/03)
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