Journal of Organic Chemistry 2010-11-05

Formation of γ-oxoacids and 1H-pyrrol-2(5H)-ones from α,β-unsaturated ketones and ethyl nitroacetate.

Maialen Aginagalde, Tamara Bello, Carme Masdeu, Yosu Vara, Ana Arrieta, Fernando P Cossío

Index: J. Org. Chem. 75(21) , 7435-8, (2010)

Full Text: HTML

Abstract

Michael addition of ethyl nitroacetate on α,β-unsaturated ketones followed by Nef oxidation under hydrolytic conditions yields γ-oxoacids instead of the corresponding α,δ-dioxoesters. A concerted decarboxylation step is proposed on the basis of computational results. Finally, conversion of the γ-ketoacids thus prepared into 1H-pyrrol-2(5H)-ones by reaction with primary amines under Paal-Knorr conditions is also reported.

Related Compounds

Related Articles:

[Experimental establishment of the maximum permissible concentration of the methyl and ethyl esters of nitroacetic acid].

1980-07-01

[Gig. Tr. Prof. Zabol. (7) , 49-51, (1980)]

Synthesis and biological evaluation of DL-4,4-difluoroglutamic acid and DL-gamma,gamma-difluoromethotrexate.

1996-01-05

[J. Med. Chem. 39(1) , 66-72, (1996)]

Facile synthesis of alpha,alpha-diisobutylglycine and anchoring its derivatives onto PAL-PEG-PS resin.

2003-12-12

[J. Org. Chem. 68(25) , 9854-7, (2003)]

Functionalization of pyrimidine and purine nucleosides at C4 and C6: C-nucleophilic substitution of their C4- and C6-(1,2,4-triazol-1-yl) derivatives.

2005-01-01

[Nucleosides Nucleotides Nucleic Acids 24(5-7) , 1043-6, (2005)]

Acid-base-catalysed condensation reaction in water: isoxazolines and isoxazoles from nitroacetates and dipolarophiles.

2012-02-13

[Chemistry 18(7) , 2081-93, (2012)]

More Articles...