72936-33-5Relevant academic research and scientific papers
4-Amino-1,5-dihydro-2H-pyrrol-2-ones from boron trifluoride catalyzed reactions of 3-amino-2H-azirines with carboxylic acid derivatives
Hugener,Heimgartner
, p. 1490 - 1498 (1995)
Reaction of 3-amino-2H-azirines 1 with ethyl 2-nitroacetate (6a) in refluxing MeCN affords 4-amino-1,5-dihydro-2H-pyrrol-2-ones 7 and 3,6-diamino-2,5-dihydropyrazines 8, the dimerization product of 1. Thus, 6a reacts with 1 as a CH-acidic compound by C-C
Efficient palladium-catalyzed cross-coupling of highly acidic substrates, nitroacetates
Metz, Alison E.,Berritt, Simon,Dreher, Spencer D.,Kozlowski, Marisa C.
supporting information; experimental part, p. 760 - 763 (2012/03/26)
Palladium-catalyzed cross-coupling conditions were developed that efficiently afford 2-aryl-2-nitroacetates from aryl bromides and the very acidic nitroacetates.
Ethynyl-1,2-benziodoxol-3(1H)-one (EBX): An exceptional reagent for the ethynylation of keto, cyano, and nitro esters
Gonzalez, Davinia Fernandez,Brand, Jonathan P.,Waser, Jerome
supporting information; experimental part, p. 9457 - 9461 (2010/10/03)
Hot alkyne! The in situ generation of ethynyl-1,2-benziodoxol-3(1H)-one (EBX) from a silyl-protected reagent by using TBAF is reported. EBX displayed exceptional acetylene transfer ability onto stabilized enolates (see scheme), even at -78 □°C. The mild reaction conditions allowed the first ethynylation reactions of linear keto, cyano, and nitro esters in high yields to give all-carbon quaternary centers or non-natural amino acids after selective reduction of the nitro group.
New Synthesis of α-Nitroalkyl- and α-Nitroaralkylcarboxylic Esters from α-Nitroalkyl- and α-Nitroaralkyl-2-oxazolines
Feuer, Henry,Bevinakatti, Hanamanthsa S.,Luo, Xuan-Gan
, p. 9 - 13 (2007/10/02)
2-Nitroalkyl- and 2-nitroaralkyl-2-oxazolines are readily converted, in one step, to α-nitroalkyl- and α-nitroaralkylcarboxylic esters on treatment with the appropriate alcohol and trifluoroacetic acid (TFA).The initial products of the ring cleavage are the TFA salts of the ammonioalkyl esters of α-nitroalkyl- and α-nitroaralkylcarboxylic acids.These salts undergo facile transesterification to the α-nitrocarboxylic esters on refluxing with the appropriate alcohol.
A Facile Synthesis of α-Amino Esters via Reduction of α-Nitro Esters Using Ammonium Formate as a Catalytic Hydrogen Transfer Agent
Ram, Siya,Ehrenkaufer, Richard E.
, p. 133 - 135 (2007/10/02)
Various nitroesters 3 were selectively and rapidly reduced to their corresponding amino esters 4 in very good yield using anhydrous ammonium formate as a catalytic hydrogen transfer agent.
The Chemistry of Aryllead(IV) Tricarboxylates. The C-Arylation of Nitroalkanes and Nitronate Salts with Aryllead Triacetates
Kozyrod, Robert P.,Pinhey, John T.
, p. 713 - 721 (2007/10/02)
2-Nitropropane reacts with phenyllead triacetate in dimethyl sulfoxide to give 2-nitro-2-phenylpropane in good yield.This arylation of nitroalkanes has been examined with a variety of substrates and a number of aryllead triacetates, and in those cases where there was no steric hindrance the reaction was found to be quite general.Reactions of nitroethane and methyl nitroacetate, compounds with two α-hydrogens, were readily controlled to give either the mono- or di-arylated products.The corresponding nitronate salts were also examined and found to undergo the arylation reaction in similar yield but at a very much faster rate.
