13250-95-8Relevant articles and documents
Limitations of the Jacobs-Gould reaction using microwave irradiation
Smith, Robert B.,Faki, Hajira,Leslie, Ray
, p. 1492 - 1499 (2011)
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.
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.
Design, synthesis and structure-activity-relationship of 1,5-tetrahydronaphthyridines as CETP inhibitors
Fernandez, Maria-Carmen,Escribano, Ana,Mateo, Ana I.,Parthasarathy, Saravanan,Martin De La Nava, Eva M.,Wang, Xiaodong,Cockerham, Sandra L.,Beyer, Thomas P.,Schmidt, Robert J.,Cao, Guoqing,Zhang, Youyan,Jones, Timothy M.,Borel, Anthony,Sweetana, Stephanie A.,Cannady, Ellen A.,Stephenson, Gregory,Frank, Scott,Mantlo, Nathan B.
scheme or table, p. 3056 - 3062 (2012/06/17)
This Letter describes the discovery and SAR optimization of 1,5-tetrahydronaphthyridines, a new class of potent CETP inhibitors. The effort led to the identification of 21b and 21d with in vitro human plasma CETP inhibitory activity in the nanomolar range (IC50 = 23 and 22 nM, respectively). Both 21b and 21d exhibited robust HDL-c increase in hCETP/hApoA1 dual heterozygous mice model.
