73308-43-7Relevant articles and documents
An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space
Gama, Fernando H. S.,De Souza, Rodrigo O. M. A.,Garden, Simon J.
, p. 70915 - 70928 (2015/09/08)
The present study describes the preparation of N-aryl-(15) and N-alkyl-(17) acetoacetamides, in good to excellent yields, using both conventional and microwave heating, by reaction of amine derivatives (14 and 16) with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD, 12) in aqueous medium. The acetoacetamides were used to prepare novel Biginelli dihydropyrimidine derivatives. The introduction of the amino acid derivatives potentially allows for the exploration of new structural complexity and topologically diversifies the chemical space occupied by this versatile chemical scaffold.
Phenyliodine bis(trifluoroacetate)-mediated oxidative C-C bond formation: Synthesis of 3-hydroxy-2-oxindoles and spirooxindoles from anilides
Wang, Junwei,Yuan, Yucheng,Xiong, Rui,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
supporting information; experimental part, p. 2210 - 2213 (2012/06/18)
The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO2Et) in CF3CH2OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1′ (E = CON(R4
Rhodium(II) Acetate and Nafion-H Catalyzed Decomposition of N-Aryldiazoamides. An Efficient Synthesis of 2(3H)-Indolinones
Doyle, Michael P.,Shanklin, Michael S.,Pho, Hoan Q.,Mahapatro, Surendra N.
, p. 1017 - 1022 (2007/10/02)
N-Aryldiazoamides undergo facile intramolecular aromatic substitution to form 2(3H)-indolinones in high yield when these reactions are performed in the presence of a catalytic amount of rhodium(II) acetate.Diazoacetamides react smoothly at room temperature in dichloromethane, whereas the corresponding less reactive diazoacetoacetamides respond in the refluxing benzene.A meta methoxy substituent directs substitution solely to its para position, but a meta methyl substituent offers virtually no selectivity for substitution.N-α-Naphtyldiazoacetamide undergoes exclusive intr amolecular substitution at the β-position.The perfluororesinsulfonic acid Nafion-H also catalyzes the decomposition of N-aryldiazoacetamides, but not N-aryldiazoacetamides, and yields of 2-idolinones are even greater than those obtained with rhodium carboxylate catalysis even though higher reaction temperatures are required to initiate decomposition