2901-29-3Relevant articles and documents
One-Pot Reaction of Carboxylic Acids and Ynol Ethers for the Synthesis of β-Keto Esters
Zeng, Linwei,Lai, Zhencheng,Cui, Sunliang
, p. 14834 - 14841 (2018/12/14)
An one-pot reaction of carboxylic acids and ynol ethers for the synthesis of β-keto esters has been developed. Under promotion of Ag2O, various carboxylic acids and ynol ethers could transform to α-acyloxy enol esters, which undergo a following DMAP-catalyzed rearrangement to deliver β-keto esters rapidly. This method provides a direct approach to β-keto esters from carboxylic acids without any preactivation. The protocol features mild reaction conditions, broad substrate scope, and the products could be transformed to an array of compounds.
Studies with 3-Oxoalkanenitriles: Synthesis of new Pyrazolopyrimidines and Pyrazolotriazines and Reactivity of 4-Phenyl-3-oxobutanenitrilke Derivatives
Khalik, Mervat Mohammed Abdel
, p. 1377 - 1389 (2007/10/03)
4-Phenyl-3-oxobutanenitrile 6 could be synthesized via reacting ethyl phenylacetate with acetonitrile in presence of sodium hydride.Although this product could not be isolated in pure form, it was identified via isolating its 2-phenylhydrazone derivative 4 and its dimethylaminomethylidene derivative 5.Both the hydrazone and the dimethylaminomethylidene derivatives proved versatile starting materials for synthesis of a variety of polyfunctionally substituted heterocycles.The reaction of 4 with hydrazine hydrate afforded 3-benzyl-4- phenylazo-1H-pyrazolo-5-amine 1.Compound 5 reacted with 3-amino-5- methylpyrazole to yield 5-benzyl-2-methylpyrazolopyrimidine-6-carbonitrile 2.The reaction of 4 with a variety of reagents enabled synthesis of a pyridazinone 10 and a benzocinnoline derivative 14.Compound 1 could be converted into pyrazolopyrimidine derivatives 17,19 by reaction with bifunctional electrophiles.In addition, compound 1 was diazotized then coupled with active methylene, β-naphthol or resorcinol affording phenylazopyrazolotriazine derivatives 22-24.
ELECTRON TRANSFER REACTIONS OF ALIPHATIC ESTERS TO THE CORRESPONDING ALIPHATIC KETONES BY LITHIUM 4,4'-DI-T-BUTYLBIPHENYL RADICAL ANION
Karaman, Rafik,Fry, James L.
, p. 4935 - 4938 (2007/10/02)
Sonication of some representative aliphatic esters with lithium in the presence of catalytic amounts of 4,4'-di-t-butylbiphenyl (DBB) in dry THF under N2 afforded the corresponding aliphatic ketones in good yields.Monitoring studies by GC/MS and 1H-NMR spectroscopy after quenching indicate the intermediacy of the corresponding β-ketoesters.
