105956-40-9Relevant academic research and scientific papers
An efficient and simple Morita-Baylis-Hillman reaction based on the N-methylpyrrolidine-Ba(OH)2 catalytic system
Guerra, Krassimira P.,Afonso, Carlos A. M.
, p. 2562 - 2569 (2011)
By using of precise catalytic amount of N-methylpyrrolidine (5 mol %) and Ba(OH)2 (1.5 mol %) in H2O/CH3OH 5/1 or CH 3OH/CH2Cl2 3/1 solvent mixtures at T=0 °C a Morita-Baylis-Hillman derivatives could be obtained in good to excellent yield from 2-cyclopenten-1-one, 2-cyclohexen-1-one and formaldehyde and diverse aryl aldehydes after suitable reaction time.
Imidazole-catalysed Baylis-Hillman reactions: A new route to allylic alcohols from aldehydes and cyclic enones
Gatri, Rafik,El Ga?ed, Mohamed Moncef
, p. 7835 - 7836 (2002)
An efficient one-pot synthesis of cyclic Baylis-Hillman adducts is described. An imidazole-catalysed coupling reaction between cyclic enones and both aliphatic and aromatic aldehydes leads to allylic alcohols in moderate to good yields.
A concise and convergent (formal) total synthesis of huperzine A
Lucey, Cathal,Kelly, Sean A.,Mann, John
, p. 301 - 306 (2007)
The first convergent synthesis of the tricyclic skeleton of huperzine A is described and includes, as the key step, an efficient regioselective intramolecular Heck reaction of 2-(tert-butyldimethylsilyloxymethyl)-6-(2- methoxy-5-bromopyridin-6-yl)methylcy
BX 3-Mediated Intermolecular Formation of Functionalized 3-Halo-1 H-indenes via Cascade Halo-Nazarov-Type Cyclization
Fernandes, Rodney A.,Kumari, Anupama
, p. 2245 - 2258 (2020)
A BX 3-promoted, intermolecular regioselective synthesis of 3-halo-functionalized 1 H-indenes from 4-oxo-4 H-chromene-3-carb?-aldehydes and alkynes has been developed. BX 3 displays a dual role of Lewis acid catalyst and halide source for haloallyl cation formation for the intended halo-Nazarov-type cyclization. The overall transformation represents an efficient cascade annulation that employs readily available starting materials, inexpensive reagents and a convenient and mild reaction procedure to generate halo-functionalized indenes (45 examples). The reaction was also extended to 8-formylcoumarins to deliver coumarin-based 3-halo-1 H-indenes in 79-95percent yield (6 examples). The reaction involves conversion of the aldehyde into an sp 3 carbon with two new C-C bonds and additionally a C-X bond is formed (X = halide).
Catalytic SNAr of unactivated aryl chlorides
Walton, James W.,Williams, Jonathan M. J.
, p. 2786 - 2789 (2015)
We present nucleophilic aromatic substitution of unsubstituted aryl chlorides via a mechanism that is catalytic in [CpRu(p-cymene)]PF6 and involves a Ru(η6-arylchloride) intermediate. From the spectroscopic evidence we infer that are
Glutathionyl Transferase Catalyzed Addition of Glutathione to COMC: A New Hypothesis for Antitumor Activity
Hamilton, Diana S.,Ding, Zhebo,Ganem, Bruce,Creighton, Donald J.
, p. 1209 - 1212 (2002)
matrix presented Data are presented indicating that the potent antitumor activity of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxy-2-cyclohexenone (COTC) and 2-crotonyloxymethyl-2-cyclohexenone (COMC) is not likely the result of glyoxalase I inhibition,
Development of pH/Glutathione-Responsive Theranostic Agents Activated by Glutathione S-Transferase πfor Human Colon Cancer
Liu, Ji,Liu, Xin,Qian, Jianqiang,Meng, Chi,Zhu, Peng,Hang, Jiaying,Wang, Yaling,Xiong, Biao,Qiu, Xiaodong,Zhu, Weizhong,Yang, Yumin,Zhang, Yanan,Ling, Yong
, p. 9271 - 9283 (2020)
Two novel theranostic agents HJTA and HJTB have been designed and synthesized by covalently linking a β-carboline derivative, with antitumor activities and pH-responsive fluorescence, with a 2-exomethylenecyclohexanone moiety, which can be activated by the tumor-targeting glutathione (GSH)/glutathione S-transferase π(GSTπ). These agents showed pH- and GSH-dual-responsive fluorescence in tumor cells but not in normal cells. Importantly, HJTA selectively illuminated tumor tissue for up to 7 h and generated precise visualization of orthotopic colonic tumors through the blood circulation system in intraoperative mice. Furthermore, HJTA exhibited potent and selective antiproliferative activities and colonic tumor inhibition in mice. Finally, HJTA induced great cancer cell apoptosis and autophagy by regulating the expression of apoptotic and autophagic proteins. Therefore, this pH/GSH-dual-responsive fluorescent probe with cancer-targeting therapeutic activity provides a novel tool for precise diagnosis and tumor treatment, therefore broadening the impact of multifunctional agents as theranostic precision medicines.
Cyclic enones as substrates in the Morita-Baylis-Hillman reaction: Surfactant interactions, scope and scalability with an emphasis on formaldehyde
Schwartz, Brett D.,Porzelle, Achim,Jack, Kevin S.,Faber, Jonathan M.,Gentle, Ian R.,Williams, Craig M.
, p. 1148 - 1154 (2009)
Traditionally, cyclic enones and formalin are reactants notorious for displaying problematic behaviour (i.e., poor solubility and low yields) under Morita-Baylis-Hillman (MBH) reaction conditions. The body of research presented herein focuses on the use o
N,N,N′,N′-Tetramethyl-1,3-propanediamine as the catalyst of choice for the Baylis-Hillman reaction of cycloalkenone: Rate acceleration by stabilizing the zwitterionic intermediate via the ion-dipole interaction
Young Lee, Ka,Gowrisankar, Saravanan,Kim, Jae Nyoung
, p. 5485 - 5488 (2004)
N,N,N′,N′-Tetramethyl-1,3-propanediamine (TMPDA) can be used as an efficient catalyst for the Baylis-Hillman reaction of cycloalkenones. The increased reaction rate was thought be derived from the stabilizing effect of the zwitterion
The intramolecular reductive cyclization of cyclic enones
Handy, Scott T.,Omune, Duncan
, p. 1366 - 1371 (2007)
The reductive cyclization (electrohydrocyclization reaction) of tethered cyclic enones has been investigated under electrochemical, metal-mediated, and photochemical conditions. The tricyclic products are generally formed with excellent stereoselectivity,
