22273-65-0

Usage

InChI:InChI=1/C10H9NO2/c12-10-6-9(7-13-10)11-8-4-2-1-3-5-8/h1-6,11H,7H2

Upstream product

• 4916-29-4 dimethyl 2-(phenyl-amino)-2-butendioate 
• 541-57-1 4-hydroxy-2(5H)-furanone 
• 62-53-3 aniline 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 4971-56-6 tetrahydrofuran-2,4-dione 
• 90766-46-4 4-anilino-3-bromo-5H-furan-2-one 

Downstream Products

• 119648-08-7 4-anilino-3-(N,N-dimethylaminoethyl)-2(5H)-furanone 
• 121694-87-9 4-(N-methylanilino)-2(5H)-furanone 
• 85422-43-1 9-phenylfuro[3,4-b]quinoline-1(3H)-one 
• 1070658-55-7 C₂₇H₂₄BrNO₇ 
• 4971-56-6 tetrahydrofuran-2,4-dione 
• 62-53-3 aniline 
• 728885-50-5 2-amino-2',5-dioxo-1-phenyl-5,7-dihydro-1H-spiro[furo[3,4-b]pyridine-4,3' indoline]-3-carbonitrile 
• 1579950-57-4 ethyl 3-oxo-1-(2-oxo-4-(phenylamino)-2,5-dihydrofuran-3-yl)isoindoline-1-carboxylate 

Relevant academic research and scientific papers

Highly active magnetically separable CuFe2O4 nanocatalyst: An efficient catalyst for the green synthesis of tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H) dione derivatives

A facile and efficient procedure has been reported for the synthesis of tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H)-diones by the condensation reaction of benzaldehydes, 1,3-cyclohexanediones and anilinolactones in the presence of CuFe2O4 as a reusable nanocatalyst with high catalytic activity in water. The notable advantages of this method are excellent isolated yields, short reaction times, simple workup procedure and little environmental impact. Graphical Abstract: [Figure not available: see fulltext.].

Synthesis of novel spirooxindoles in water by using MnFe2O 4 nanoparticles as an efficient magnetically recoverable and reusable catalyst

An efficient, clean, atom-economical and simple method for the one-pot synthesis of novel spirooxindole derivatives via a three-component reaction of isatins, dimedone and anilinolactones was reported. This reaction was performed by using MnFe2O4 nanoparticles (5 mol%) as an efficient magnetically heterogeneous catalyst in water as green solvent. Prominent among the advantages of this method is the use of magnetically recoverable and reusable catalyst, simple work up procedure, good to high product yields and use of water as a solvent that is considered to be relatively environmentally benign.

Synthesis of 3-bromotetronamides via amination of 3,4-dibromofuran-2(5H)- one

This work describes the direct synthesis of 3-bromotetronamides in good yields through the reaction of 3,4-dibromofuran-2(5H)-one, obtained from furfural, with primary and secondary amines. Aromatic amines were more tolerated than aliphatic and heteroaromatic ones. The X-ray structures of five derivatives are described.

Polyalkoxybenzenes from plants. 5. parsley seed extract in synthesis of azapodophyllotoxins featuring strong tubulin destabilizing activity in the sea urchin embryo and cell culture assays

A series of 4-azapodophyllotoxin derivatives with modified rings B and E have been synthesized using allylpolyalkoxybenzenes from parsley seed oil. The targeted molecules were evaluated in vivo in a phenotypic sea urchin embryo assay for antimitotic and tubulin destabilizing activity. The most active compounds identified by the in vivo sea urchin embryo assay featured myristicin-derived ring E (4e, 6e, and 8e). These molecules were determined to be more potent than podophyllotoxin. Cytotoxic effects of selected molecules were further confirmed and evaluated by conventional assays with A549 and Jurkat human leukemic T-cell lines including cell growth inhibition, cell cycle arrest, cellular microtubule disruption, and induction of apoptosis. The ring B modification yielded 6-OMe substituted molecule 8e as the most active compound. Finally, in Jurkat cells, compound 8e induced caspase-dependent apoptosis mediated by the apical caspases-2 and -9 and not caspase-8, implying the involvement of the intrinsic caspase-9-dependent apoptotic pathway.

A facile synthesis of the 4-aza-analogs of 1-arylnaphthalene lignans chinensin, justicidin B, and Taiwanin C

Reaction of anilines 1a-d with retronic acid (2) or 1,3- cyclopentanedione (3) produced anilinolactones 4a-d and anilinocyclopentenone 5a, respectively, which were then condensed with benzaldehydes to yield 4- aza-1-arylnaphthalene lignan analogs 6-19.

Mechanism of hydrolysis and structure-stability relationship of enaminones as potential prodrugs of model primary amines

The objective of this work was to investigate the chemistry and the structure-stability relationship of enaminones (a class of enamines formed between a primary amine and a 1,3-dicarbonyl compound) and to evaluate their potential usefulness as prodrugs of primary amines. The acid-catalyzed degradation of the enaminones was found to be very sensitive to minor differences in the structure of the 1,3-dicarbonyl compound used to form the enaminone, but relatively insensitive to changes in the amine portion of the enaminones. A correlation was found between the rate of enaminone hydrolysis and the pK(a) of the 1,3-dicarbonyl compound, suggesting that the rate-controlling step in the hydrolysis of the enaminones was the proton addition to the vinyl carbon of the enaminone. Enaminones formed with cyclic 1,3-dicarbonyl compounds were significantly more stable than those formed with structurally similar acyclic compounds. Based on chemical stability considerations alone, enaminones do not appear to be good candidates as prodrugs of primary amines. Evidence is presented, however, that enaminones formed between amines and 1,3-ketoesters or lactones may be subject to enzyme-catalyzed degradation. Further research on the design of enaminones destabilized by a triggering enzymatic event that results in the loss of conjugation (e.g., ester or lactone hydrolysis or an oxidation/reduction event) may prove worth pursuing.

Enaminones as potential prodrugs of primary and secondary amines

Novel enzymatically labile enaminones useful as potential prodrugs of primary and secondary amines are disclosed. Also, disclosed herein are compositions comprising said amines and methods of administering said composition to warm-blooded animals.

2(3H)- AND 2(5H)-FURANONES. III. AN EFFICIENT SYNTHESIS AND THE ESCHENMOSER-MANNICH REACTION OF N-SUBSTITUTED 4-AMINO-2(5H)-FURANONE

A series of N-substituted 4-amino-2(5H)-furanones (II) was derived from β-tetronic acid (I) by direct action of several aliphatic and aromatic amines.The Eschenmoser-Mannich reaction of II readily gave the corresponding Mannich bases (VI) quantitatively.