14003-19-1

Basic information

• Product Name: ETHYL 2-NITRILO-2-(2-OXOINDOLIN-3-YLIDENE)ACETATE
• Synonyms: ETHYL 2-NITRILO-2-(2-OXOINDOLIN-3-YLIDENE)ACETATE;AKOS BC-1555
• CAS NO: 14003-19-1
• Molecular Formula: C₁₃H₁₀N₂O₃
• Molecular Weight: 242.23
• Product Categories: Esters;Pyrroles & Indoles
• Mol File: 14003-19-1.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL 2-NITRILO-2-(2-OXOINDOLIN-3-YLIDENE)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-NITRILO-2-(2-OXOINDOLIN-3-YLIDENE)ACETATE(14003-19-1)
• EPA Substance Registry System: ETHYL 2-NITRILO-2-(2-OXOINDOLIN-3-YLIDENE)ACETATE(14003-19-1)

Safety Data

• Hazardous Substances Data: 14003-19-1(Hazardous Substances Data)

Upstream product

• 59-48-3 2-oxoindole 
• 105-56-6 ethyl 2-cyanoacetate 
• 91-56-5 indole-2,3-dione 
• 13504-72-8 triphenylphosphorane 
• 14003-18-0 3-methylene-2-indolinone 

Downstream Products

• 83451-58-5 2-Amino-3-ethoxycarbonyl-4-quinolyl-1-phenyl-5-oxo-2-pyrazolin-4-yl ketone 
• 106536-40-7 ethyl 6′-amino-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carboxylate 
• 138197-38-3 6'-Amino-2-oxo-1',3'-diphenyl-spiro<2,3-dihydro-indol-3,4'-pyrano<2,3-c>pyrazol>-5'-carbonsaeure-ethylester 
• 74647-44-2 5'-acetyl-2'-amino-3'-ethoxycarbonyl-6'-methylspiro-2-one 
• 74647-46-4 2'-amino-5'-benzoyl-3'-ethoxycarbonyl-6'-methylspiro-2-one 
• 26960-51-0 ethyl (E)-2-(1-benzyl-2-oxoindolin-3-ylidene)-2-cyanoacetate 
• 1361403-92-0 ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate 
• 1210910-09-0 2-benzyl-3a-(ethoxycarbonyl)-4-oxo-3-spiro(3-indolyl-2-one)-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-2-carboxylic acid 
• 210232-93-2 ethyl 2-amino-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carboxylate 
• 1155873-30-5 4,3'-spiro(ethyl 3-acetyl-6-amino-1-phenyl-1,4-dihydropyridazine-5-carboxylate)-2'-oxindole 
• 1123744-18-2 ethyl 5-amino-3-cyano-2-oxo-1-(4'-methylphenyl)-1,1',2',3a,7,7a'-hexahydrospiro[indole-3',7-pyrano[3,2-b]pyrrole]-6'-carboxylate 

Relevant articles and documents

E,Z Isomerization Studies of Ethyl 2-Oxo-3-Indolinylidenecyanoacetates by 1H NMR Spectroscopy

The kinetics of base-catalysed E/Z isomerization for a series of ethyl 2-oxo-3-indolinylidenecyanoacetates in CDCl3 solutions were studied by 1H NMR spectroscopy.Both polarizable double bond considerations and steric requirements of the base must be considered in explaining the results.The E/Z equilibrium of ethyl 1-carbethoxy-2-oxo-3-indolinylidenecyanoacetate was reached faster than those of ethyl 2-oxo-3-indolinylidenecyanoacetate and the 1-methyl derivative by a factor of ca. 10 in the presence of triethylamine, and the isomerization were faster when quinuclidine was used.In pure DMSO-d6 solutions, the equilibria were established upon dissolution, but addition of small amounts of acid slowed the isomerization process in these systems.Key words: E/Z isomerization, 1H NMR, Ethyl-2-oxo-3-indolinylidenecyanoacetates

Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon-carbon double bond formation

The iron-catalyzed cross-dehydrogenative coupling (CDC) of C(sp3)-H/C(sp3)-H bonds to afford olefins by 4H elimination is described. This method employs air (molecular oxygen) as an ideal oxidant, and is performed under mild, ligand-free and base-free conditions. H2O is the only byproduct. Good tolerance of functional groups and high yields have also been achieved. Preliminary mechanistic investigations suggest that the present transformation involves a radical process.

Copper-catalyzed hydroboration of alkenyl oxindoles

Herein we describe the NHC-Cu(I)-catalyzed hydroboration of alkenyl oxindoles. The corresponding boronates were obtained in good yields, under operationally simple and environmentally friendly conditions, using ethanol as the solvent. Our studies revealed that water-based systems were not very effective. Furthermore, the obtained products are amenable to further elaboration and can be useful to the synthesis of a broader range of oxindole-containing molecules with biological relevance.