73308-43-7

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 758640-21-0 N-Benzylaniline 
• 6840-29-5 N-phenyl-N-benzylacetamide 
• 541-50-4 2-acetoacetic acid 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 

Downstream Products

• 935733-32-7 1-benzyl-3-(1-hydroxyethylidene)indolin-2-one 
• 112482-66-3 N-benzyl-N-phenyl-2-diazo-3-oxobutanamide 
• 1373442-88-6 N-benzyl-2-hydroxy-3-oxo-N-phenylbutanamide 
• 1436432-46-0 1-benzyl-3-hydroxy-4-methylquinolin-2(1H)-one 
• 112482-84-5 1-benzyl-3-acetyl-2-indolinone 
• 112482-71-0 N-benzyl-2-diazo-N-phenylacetamide 
• 7135-32-2 1-benzylindolin-2-one 

Relevant academic research and scientific papers

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

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.

One-pot synthesis of 3-hydroxyquinolin-2(1 H)-ones from N-phenylacetoacetamide via PhI(OCOCF3)2-mediated α-hydroxylation and H2SO4-promoted intramolecular cyclization

A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF 3)2-mediated α-hydroxylation and a H 2SO4-promoted intramolecular condensation. The hydroxyl group in the generated α-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.

Phenyliodine bis(trifluoroacetate)-mediated oxidative C-C bond formation: Synthesis of 3-hydroxy-2-oxindoles and spirooxindoles from anilides

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

Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles

With [Ru(p-cymene)Cl2]2 as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C-H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (kH/kD ～ 1) suggests that the reaction should not proceed by rate-limiting C-H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.

Rhodium(II) Acetate and Nafion-H Catalyzed Decomposition of N-Aryldiazoamides. An Efficient Synthesis of 2(3H)-Indolinones

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

ORGANOMETALLIC INDUCED SELF-CONDENSATION OF CARBOXAMIDES

N,N-Disubstituted carboxamides containing α-hydrogen atoms undergo self-condensation reaction simply on treatment with Grignard reagents or n-BuLi in THF at room temp.The reaction is considerably influenced by steric hindrance at the α-carbon and the condensing agent utilized.A possible Claisen-type mechanism is also reported.

Reductive Ring Contraction of Mesoionic Thiazol-4-ones to Azetidin-2-ones

A series of anhydro-2,3,5-triaryl-4-hydroxythiazolium hydroxides was prepared and desulfurized with Raney nickel.The reduction was stereospecific and gave cis-1,3,4-triphenylazetidin-2-ones.Desulfurization in the presence of triphenylphosphine gave the corresponding trans-azetidinones.Consideration of the possible mechanistic pathways led to the conclusion that the reaction proceeds through formation of biradical-dipole, hydrogenation to a 1,4-dipole, and ring closure.It was also concluded that in the preparation of β-lactams by the nonconcerted cycloaddition of imines and ketenes the first step (dipole formation) is the stereochemistry-determining step.