39080-52-9Relevant articles and documents
On the Regioselectivity of the Gould–Jacobs Reaction: Gas-Phase Versus Solution-Phase Thermolysis
Boese, A. Daniel,Dallinger, Doris,Darvas, Ferenc,Hartmann, Peter E.,Kappe, C. Oliver,Sipos, Gellért,Wernik, Michaela
, p. 7051 - 7061 (2020/11/30)
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.
MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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Page/Page column 74-75, (2020/01/08)
The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.
A simple and efficient synthesis of novel naphthyridine-1-H-pyrazole-4- carboxylic acid esters/carbaldehydes using Vilsmeier-Haack reagent
Chaitanya, Muggu V.S.R.K.,Dubey, Pramod K.
, p. 49 - 55 (2013/05/23)
The reaction of hydrazide 4 with β-keto esters 5 gave hydrazones 6. Cyclization of 6 with Vilsmeier-Haack reagent (DMF-POCl3 ) for 20 min at room temperature gave 1-(4-oxo-1,4-dihydro-[ 1 ,8]naphthyridine-3-carbonyl)- 1 H -pyrazole-4-carboxylic acid ethyl esters 7. The treatment of 4 with substituted acetophenones 8 yielded the corresponding hydrazones 9 of substituted aceto phenones. The treatment of 9 with Vilsmeier-Haack reagent (DMF-POCl3) for 30 min at room temperature gave product 10, the reaction of which with (diacetoxyiodo)benzene in ethanol at room temperature for 12 h in the presence of molecular iodine furnished 7.
