183280-15-1Relevant articles and documents
Supramolecular Pd(II) complex of DPPF and dithiolate: An efficient catalyst for amino and phenoxycarbonylation using Co2(CO)8 as sustainable C1 source
Gaikwad, Vinayak V.,Mane, Pravin A.,Dey, Sandip,Patel, Divya,Bhanage, Bhalchandra M.
, (2019/11/28)
Highly active, efficient and robust “dppf ligated tetranuclear palladium dithiolate complex” was synthesized and applied as a catalyst for chemical fixation of carbon monoxide for the synthesis value added chemicals such as tertiary amide and aromatic esters. The synthesized catalyst was characterized using different analytical techniques such as elemental analysis, 1H and 31P NMR spectroscopy. The use of Co2(CO)8 as a cheap, less toxic and low melting solid surrogate are additional advantages over the current protocol. The catalyst showed superior activity towards the Amino (10?3 mol % catalyst) and Phenoxycarbonylation (10-2 mol % catalyst) and high TON (104 to 103) and TOF (103 to 102 h-1). The Betol and Lintrin (active drug molecules) were synthesized under an optimized reaction condition. The scalability of the current protocol has been demonstrated up-to the gram level.
Electrodimerization of N-Alkoxyamides for Zinc(II) Catalyzed Phenolic Ester Synthesis under Mild Reaction Conditions
Subramanian, Kripa,Yedage, Subhash L.,Bhanage, Bhalchandra M.
, p. 2511 - 2521 (2018/05/14)
An electrochemical On-Off method for phenolic ester synthesis from N-alkoxyamides has been reported. This one-pot protocol begins with rapid and selective electrodimerization of the amide using n-Bu4NI (TBAI) as an electrocatalyst. The reaction proceeds further in the absence of current via Zn catalyzed C?N bond activation of the amide dimer followed by its coupling with phenol to form the ester. The present methodology is ligand-free and takes place under mild reaction conditions. This transformation incorporates a wide variety of phenols and amide substrates leading to the formation of functionalized esters highlighting its versatility. (Figure presented.).
Structure-activity relationships of novel azomethine prodrugs of the histamine H3-receptor agonist (R)-α-methylhistamine: From alkylaryl to substituted diaryl derivatives
Krause,Rouleau,Stark,Garbarg,Schwartz,Schunack
, p. 720 - 726 (2007/10/03)
This study was performed on the basis of recently developed prodrugs of the histamine H3-receptor agonist (R)-α-methylhistamine (1) to determine structure-activity relationships of azomethine prodrugs of 1, in which the primary amine functionality is bioreversibly linked to aromatic ketones. Therefore, the pro-moiety was systematically altered from alkylaryl over benzylaryl to diaryl substitution. Those compounds that emerged to be stable enough during preparation were tested for their in vitro hydrolysis rates. Apparently, bulky alkyl residues were capable of preventing previously observed intramolecular cyclization, but the obtained azomethines 12 a-c were far too unstable to serve as prodrugs. However, the benzylaryl imines 12d, e were stable compounds, but 12d decomposed too rapidly under in vitro conditions. Distinctly greater stability was provided by diaryl pro-moieties, even if strongly electron-withdrawing functionalities were introduced. Selected compounds were also tested in vivo following p.o. application to mice. Particularly the trifluoromethyl substituted imine 12i proved to be highly effective as stability and rate of conversion were well-balanced, so that brain penetration of 1 was strikingly facilitated. Thus 12i, a highly potent azomethine prodrug, may serve as an important pharmacological tool and, possibly, a therapeutic agent.
