30853-80-6Relevant academic research and scientific papers
Synthesis of trans-1,8,12,13-tetraoxadispiro[4.1.4.2]-tridecanes - A new class of peroxides
Naveen Kumar,Sudhakar,Rao, B. Venkateswara,Kishore, K. Hara,Murty, U. Suryanarayana
, p. 771 - 774 (2006)
The synthesis of trans-1,8,12,13-tetraoxadispiro[4.1.4.2]tridecanes, a new class of peroxide skeletons using Birch reduction of aromatic compounds followed by ozonolysis and acid catalysed cyclisation is described.
Identification of N-Hydroxycinnamamide analogues and their bio-evaluation against breast cancer cell lines
Shukla, Akhilesh Kumar,Hamidullah,Shrivash, Manoj Kumar,Tripathi, Vishwa Deepak,Konwar, Rituraj,Pandey, Jyoti
, p. 475 - 483 (2018/08/21)
The present study demonstrates the identification of N-hydroxycinnamamide derivatives and their anticancer potential against human triple-negative breast cancer cell line MDA-MB?231, MCF-7 and non-malignant origin cell line, HEK-293 (human embryonic kidney). MTT assay was studied with HEK-293 cell line. Anticancer potential of the N-hydroxycinnamamide derivatives were compared with marked drug Tamoxifen through in vitro study. The compound numbers 3b and 3h exhibit most potent activity against antagonistic breast cancer cells (MDA-MB-231) with IC50 13μM and 5μM respectively. Compound 3h promotes DNA fragmentation and induction of apoptosis. Furthermore, loss of mitochondrial membrane potential induced by compound 3h. The major mechanism of compound 3h for anti-breast cancer activity was probably initiation of reactive oxygen species (ROS) in cancer cells thereby persuading apoptotic cell deaths in cancer cells.
Ligand-accelerated non-directed C-H functionalization of arenes
Wang, Peng,Verma, Pritha,Xia, Guoqin,Shi, Jun,Qiao, Jennifer X.,Tao, Shiwei,Cheng, Peter T. W.,Poss, Michael A.,Farmer, Marcus E.,Yeung, Kap-Sun,Yu, Jin-Quan
, p. 489 - 493 (2017/11/28)
The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.
Piperidine-appended imidazolium ionic liquid as task-specific basic-IL for Suzuki and Heck reactions and for tandem Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck protocols
Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
, p. 150 - 161 (2017/06/30)
Facile, high yielding, one-pot methods for the synthesis of a library of diversely substituted bi-aryls, diarylethenes, and aryl-enoates, via Suzuki and Heck reactions, and by sequential Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck reactions are reported. The reactions employ piperidine-appended imidazolium ionic liquid [PAIM][NTf2] as a task-specific basic-IL, butyl-methyl-imidazolium ionic liquid [BMIM][X] (X?=?PF6, BF4) as solvent, and catalytic amounts of Pd(OAc)2 with no other additives. Wittig and Horner-Emmons reactions are effected by reacting substituted benzaldehydes with 4-bromobenzyl-PPh3 (or bromomethyl-PPh3) phosphonium salts, or diethylphosphonate with bromobenzaldehydes respectively, to form the corresponding ethenes. Subsequent cross-coupling reactions are accomplished by addition of aryl-boronic acid or phenyl-ethenes along with Pd(OAc)2 to bring about the aforementioned hyphenated transformations. The feasibility to perform double-olefination via Wittig and Horner-Emmons reactions with dialdehydes to form highly conjugated bis-styryl and bis-enoate compounds is also shown. The [BMIM][X] solvent is recycled and reused.
Heterogeneous photocatalysed Heck reaction over PdCl2/TiO 2
Waghmode, Suresh B.,Arbuj, Sudhir S.,Wani, Bina N.
, p. 2911 - 2916 (2013/09/12)
The heterogeneous PdCl2/TiO2 efficiently catalyzes the C-C bond formation (Heck reaction) between aryliodides and olefins under photochemical and mild reaction conditions. This process gives good to excellent conversion under optimized reaction conditions. After completion of the reaction, Pd2+ is reduced to Pd0. Further, Pd0 can be easily converted into Pd2+ by heating with ammonium chloride at 400°C for 30 min and the regenerated catalyst could be reused up to the third recycle with good catalytic activity. The catalysts (before and after reaction, as well as regenerated) were systematically characterized using Transmission Electron Microscopy, X-ray photoelectron spectroscopy, X-ray diffraction, temperature programmed reduction and DRUV-visible spectroscopy techniques.
Palladium chloride catalyzed photochemical Heck reaction
Waghmode, Suresh B.,Arbuj, Sudhir S.,Wani, Bina N.,Gopinath
supporting information, p. 348 - 351 (2013/06/04)
PdCl2 catalyzed carbon-carbon bond formation (Heck reaction) between substituted aryl halides and olefins was carried out without a ligand, under irradiation with UV-visible light. The results demonstrated that UV-visible light accelerated the rate of the reaction, leading to an excellent yield of corresponding products. The recovered palladium nanoparticles could be thermally recycled several times. PdCl2 gave excellent conversion up to the fifth addition of substrate.
Solid supported palladium(0) nano/microparticle: A ligand-free efficient recyclable heterogeneous catalyst for mono- and β,β-double-Heck reaction
Sharma, Dharminder,Kumar, Sandeep,Shil, Arun K.,Guha, Nitul Ranjan,Bandna,Das, Pralay
supporting information, p. 7044 - 7051 (2013/01/15)
Solid supported palladium nano/microparticles were found to be active catalysts to perform mono- and β,β-double-Heck reactions. Different β-unsubstituted and substituted alkenes including acrylate, methacrylate, crotonate, styrene, acrylonitrile, and acrylamide were investigated successfully for mono- and β,β-double-Heck reactions with aryl iodide under milder reaction condition. One-pot β,β-double-Heck reaction of aryl iodides with α,β-unsaturated ester, amide, nitrile, and styrene derivatives were also performed under standard reaction conditions. Wide functional group tolerance, easy catalyst recovery, and recyclability up to twelve times without significant loss of catalytic activity added extra importance to the present process.
Palladium supported on a polyionic resin as an efficient, ligand-free, and recyclable catalyst for Heck, Suzuki-Miyaura, and Sonogashira reactions
Basu, Deb,Das, Sajal,Das, Pralay,Mandal, Bablee,Banerjee, Dipanjan,Almqvist, Fredrik
experimental part, p. 1137 - 1146 (2009/12/01)
Polyionic Amberlite resin formate (ARF), derived from commercially available Amberlite resin chloride by simple rinsing with aqueous formic acid, could be soaked with palladium(0) from palladium salts, the formate counteranion being the reducing source. The resulting Amberlite resin formate supported with palladium(0), ARF-Pd, showed excellent catalytic activity in Heck, Suzuki-Miyaura, and Sonogashira couplings with a range of substrates. The catalyst may be recovered easily and quantitatively without leaching and recycled; it was tested for five runs without any significant loss of activity. Georg Thieme Verlag Stuttgart.
Phosphine-free Pd-salen complexes as efficient and inexpensive catalysts for Heck and Suzuki reactions under aerobic conditions
Borhade, Sanjay R.,Waghmode, Suresh B.
, p. 3423 - 3429 (2008/09/21)
Phosphine-free palladium-salen complexes, N,N′-bis(salicylidene)-ethylenediamino-palladium and N,N′-bis(salicylidene)-1,2-phenylenediamino palladium, are found to be highly active catalysts for the Heck olefination of aryl iodides and Suzuki reaction of aryl iodides and bromides giving excellent yields (70-90%) of products under aerobic conditions, in short reaction times (10-60 min).
A practical, efficient, and atom economic alternative to the Wittig and Horner-Wadsworth-Emmons reactions for the synthesis of (E)-α,β- unsaturated esters from aldehydes
List, Benjamin,Doehring, Arno,Hechavarria Fonseca, Maria T.,Job, Andreas,Rios Torres, Ramon
, p. 476 - 482 (2007/10/03)
We describe a highly efficient new methodology for the synthesis of (E)-α,β-unsaturated esters from aldehydes. In our DMAP-catalyzed reaction, both aromatic as well as aliphatic aldehydes furnish the desired products highly regio- and stereoselectively if treated with commercially available or synthetically easily accessible malonic acid half ester. A large scale application in the synthesis of p-methoxycinnamates, which are of use as sunscreen ingredients, is described.
