5435-82-5

Usage

InChI:InChI=1/C12H12N2O3/c1-3-17-12(16)9-6-13-10-5-4-8(2)7-14(10)11(9)15/h4-7H,3H2,1-2H3

Upstream product

• 19056-89-4 diethyl 2-(((5-methylpyridin-2-yl)amino)methylene)malonate 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 64050-17-5 3-(5-methyl-[2]pyridylamino)-acrylic acid 
• 33359-68-1 7-methyl-4-oxo-4H-pyrido-[1,2-a]pyrimidine-3-carboxylic acid 

Relevant academic research and scientific papers

On the Regioselectivity of the Gould–Jacobs Reaction: Gas-Phase Versus Solution-Phase Thermolysis

A detailed investigation of the regioselectivity in the thermal cyclization of (pyridyl)aminomethylenemalonates both in the gas- and solution phase is presented. Flash vacuum pyrolysis (FVP) as a gas-phase thermolysis technique is used to study the Gould–Jacobs reaction at temperatures between 450–650 °C, while different solution-phase heating techniques (reflux, microwave, and continuous flow) were employed at 260–350 °C. Depending on the position of the substituent in the pyridine moiety and the applied thermolysis technique, the regioselectivity of the cyclization can be controlled either in favor of the kinetic (pyridopyrimidinone) or the thermodynamic (naphthyridinone) product. Under FVP conditions, 6-substituted pyridopyrimidinones were obtained in high regioselectivity, which was not demonstrated before under standard Gould–Jacobs reaction conditions. DFT calculations have been additionally performed to provide further insights into the mechanistic pathways of this specific Gould–Jacobs reaction.

Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor

Fused pyrimidinone and quinolone derivatives that are of potential interest to pharmaceutical research were synthesized within minutes in up to 96% yield in an automated Phoenix high-temperature and high-pressure continuous flow reactor. Heterocyclic scaffolds that are either hard to synthesize or require multisteps are readily accessible using a common set of reaction conditions. The use of low-boiling solvents along with the high conversions of these reactions allowed for facile workup and isolation. The methods reported herein are highly amenable for fast and efficient heterocycle synthesis as well as compound scale-ups.

Limitations of the Jacobs-Gould reaction using microwave irradiation

Upon investigating the green synthesis of some antimicrobial quinolone compounds, some atypical ring-closing patterns were observed during the synthesis of various intermediates using the Jacobs-Gould reaction.

SUBSTITUTED AMIDE DERIVATIVES AS PROTEIN KINASE INHIBITORS

Selected compounds are effective for prophylaxis and treatment of diseases, such as HGF mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.