98841-65-7

Usage

InChI:InChI=1/C13H16N2O3/c1-17-11-4-3-10(9-12(11)18-2)6-8-15-13(16)5-7-14/h3-4,9H,5-6,8H2,1-2H3,(H,15,16)

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 105-56-6 ethyl 2-cyanoacetate 
• 105-34-0 methyl 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 43052-77-3 (3,4-dihydro-6,7-dimethoxyisoquinolin-1-yl)acetonitrile 
• 138574-63-7 3-Oxo-1,4-diaza-spiro[4.5]dec-1-ene-2-carboxylic acid [2-(3,4-dimethoxy-phenyl)-ethyl]-amide 
• 133550-45-5 (E)-2-Cyano-3-(3,4-dihydroxy-phenyl)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acrylamide 
• 913819-74-6 1-(2-(3,4-dimethoxyphenyl)ethyl)-5-hydroxy-4,5-dimethyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile 
• 1261167-44-5 C₁₉H₂₀ClN₃O₃ 
• 1315060-74-2 2-(3,4-dimethoxyphenyl)-3-methyl-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carbonitrile 
• 1315060-75-3 N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}benzamide 
• 1315060-76-4 N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}-3-iodobenzamide 
• 1164524-78-0 N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}-4-chlorobenzamide 
• 1315060-77-5 N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}-2-fluorobenzamide 
• 1164549-29-4 N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}-4-methoxybenzamide 
• 1315060-79-7 N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}benzenesulfonamide 
• 1315060-80-0 N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}-3-chlorobenzenesulfonamide 
• 1315060-81-1 N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}-3-nitrobenzenesulfonamide 

Relevant academic research and scientific papers

Cyanoacetamides (IV): Versatile one-pot route to 2-quinoline-3-carboxamides

Cyanoacetic acid derivatives are the starting materials for a plethora of multicomponent reaction (MCR) scaffolds. Herein, we describe scope of a valuable general protocol for the synthesis of arrays of 2-aminoquinoline-3-carboxamides from cyanoacetamides and 2-aminobenzaldehydes or heterocyclic derivatives via a Friedlaender reaction variation. In many cases, the reactions involve a very convenient work up by simple precipitation and filtration. More than 40 new products are described. We foresee our protocol and the resulting derivatives becoming very valuable to greatly expanding the scaffold space of cyanoacetamide derivatives.

6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidenoacetonitrile in some fusion reactions

6,7-Dimethoxy-3,4-dihydroisoquinolin-1-ylacetonitrile in the enamine form readily reacts with acyl iso(thio)cyanates affording in high yields 1,2-fused oxo- and thioxodihydropyrimidoisoquinolines and thiouracyloisoquinolines. The reaction of the enamine with primary amines of diverse classes in the presence of 2 equiv of formaldehyde resulted in 1,2-fused N-substituted tetrahydropyrimidinoisoquinolines whose yields depended on the basicity and sterical accessibility of the reagent. Fused 5-hydroxyindolo-, dioxopyrrolo-, pyrroloisoquinolines formed in medium yields in the one-stage reactions of the enamine with p-benzoquinone, oxalyl chloride, and β-nitrostyrene respectively. The reaction of 1-cyanomethyl-6,7-dimethoxydihydroisoquinoline with acrylonitrile leads to the formation of 1,2-fused iminopyridinoisoquinoline easily hydrolysable to pyridine derivative and readily reacting by the amidine group with aroyl chlorides and arylsulfonyl chlorides. Pleiades Publishing, Ltd., 2011.

Synthesis of N-substituted γ-methylene γ-lactams

N-Substituted cyanoacetamides 1 were condensed with 1,2-diketones 2 under base catalysis to form ?-hydroxy ?-lactams 3. Treatment of 3 with acids gave novel fungicidal ?-methylene ?-lactams 4. The exocyclic double bond of 4b reacted reversibly with 4-toluene sulfinate. CSIRO 2005.

PYRROLODIHYDROISOQUINOLINES AS PDE10 INHIBITORS

The invention relates to novel pyrrolodihydroisoquinoline derivatives, which are efficacious inhibitors of PDE10.

Tyrphostins. 2. Heterocyclic and α-Substituted Benzylidenemalonitrile Tyrphostins as Potent Inhibitors of EGF Receptor and ErbB2/neu Tyrosine Kinases

We have previously described a novel series of low molecular weight protein tyrosine kinase inhibitors which we named tyrphostins.The characteristic active pharmacophore of these compounds was the hydroxy-cis-benzylidenemalonitrile moiety.In this article we describe three novel groups of tyrphostins: (i) one group has the phenolic moiety of the cis-benzylidenemalononitrile replaced either with other substituted benzenes or with heteroaromatic rings, (ii) another is a series of conformationally constrained derivatives of hydroxy-cis-benzylidenemalononitriles in which the malononitrile moiety is fixed relative to the aromatic ring, and (iii) two groups of compounds in which the position trans to the benzenemalononitrile has been substituted by ketones and amides.Among the novel tyrphostins examined we found inhibitors which discriminate between the highly homologous EGF receptor kinase (HER1) and ErbB2/neu kinase (HER2).These findings may lead to selective tyrosine kinase blockers for the treatment of diseases in which ErbB2/neu is involved.