49655-73-4Relevant academic research and scientific papers
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.
Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor
Tsoung, Jennifer,Bogdan, Andrew R.,Kantor, Stanislaw,Wang, Ying,Charaschanya, Manwika,Djuric, Stevan W.
, p. 1073 - 1084 (2018/06/18)
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.
2-Arylindoles as gonadotropin releasing hormone (GnRH) antagonists: Optimization of the tryptamine side chain
Young, Jonathan R.,Huang, Song X.,Walsh, Thomas F.,Wyvratt Jr., Matthew J.,Yang, Yi Tien,Yudkovitz, Joel B.,Cui, Jisong,Mount, George R.,Ren, Rena Ning,Wu, Tsuei-Ju,Shen, Xiaolan,Lyons, Kathryn A.,Mao, An-Hua,Carlin, Josephine R.,Karanam, Bindhu V.,Vincent, Stella H.,Cheng, Kang,Goulet, Mark T.
, p. 827 - 832 (2007/10/03)
A series of 2-arylindoles containing novel heteroaromatic substituents on the tryptamine tether, based on compound 1, was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. Successful modifications of 1 included chain length variation (reduction) and replacement of the pyridine with heteroaromatic groups. These alterations culminated in the discovery of compound 27kk which had excellent in vitro potency and oral efficacy in rodents.
Palladium(0)-catalyzed coupling of 6-bromo and 3-iodo derivatives of 7- methyl-4-oxo-1,4-dihydro[1,8]naphthyridines
Plisson, Christophe,Chenault, Jacques
, p. 2627 - 2638 (2007/10/03)
Substituted 4-oxo-1,4-dihydro[1,8]naphthyridines were obtained with various substituents (aryl, alkyl, carbonyl chains) by functionalization at positions 6 and 3 using a Suzuki, Heck or Stille reaction.
