61997-76-0Relevant academic research and scientific papers
Hypervalent Iodine(III)-Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β-Enaminone to Carbazolone and Imidazo[1,2-a]pyridine Synthesis
Bhattacherjee, Dhananjay,Ram, Shankar,Chauhan, Arvind Singh,Yamini,Sheetal,Das, Pralay
supporting information, p. 5934 - 5939 (2019/04/08)
A highly efficient and flexible protocol for intramolecular annulation of exocyclic β-enaminones has been disclosed for the synthesis of carbazolones and imidazo[1,2-a]pyridines through a counter-anion-controlled free-radical mechanism promoted by hypervalent iodine(III). The cooperative behavior of HTIB and AgSbF6 plays a crucial role in the intramolecular annulation process through C?C and C?N bond formation to give the desired products. The mechanistic insights suggest that the two competitive reactions involved in the system are guided by the nature of the counteranion, which determines the formation of the final products. A wide variety of carbazolones and imidazo[1,2-a]pyridine molecules have been prepared and isolated in good to excellent yields.
Catalyst-free Synthesis of Tetrahydroacenaphtho[1,2-b]indolone Derivatives via One-pot Four-component Reaction
Bayat, Mohammad,Amiri, Zeinab
, p. 1346 - 1351 (2018/04/14)
A simple and efficient one-pot synthesis of tetrahydroacenaphtho[1,2-b]indolone derivatives via four-component reaction of 5,5-dimethylcyclohexane-1,3-dione (dimedone), arylamines, acenaphthoquinone, and active methylene compounds under catalyst-free conditions is described. The reactions were carried out under mild conditions using ethanol as solvent. Advantages of this method include simple experimental and workup procedure, readily available starting materials, and high yields.
Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9
Lobo, Gricela,Monasterios, Melina,Rodrigues, Juan,Gamboa, Neira,Capparelli, Mario V.,Martínez-Cuevas, Javier,Lein, Michael,Jung, Klaus,Abramjuk, Claudia,Charris, Jaime
, p. 281 - 295 (2015/04/27)
A highly regiospecific synthesis of a series of indenoindoles is reported, together with X-ray studies and their activity against human prostate cancer cells PC-3 and LNCaP in vitro. The most effective compound 7,7-dimethyl-5-[(3,4-dichlorophenyl)]-(4bRS,9bRS)-dihydroxy-4b,5,6,7,8,9bhexahydro-indeno[1,2-b]indole-9,10-dione 7q reduced the viability in both cell lines in a time and dose-dependent manner. Inhibitory effects were also observed on the adhesion, migration, and invasion of the prostate cancer cells as well as on clonogenic possibly by inhibition of MMP-9 activity. Molecular docking of 7q and 6k into MMP-9 human active site was also performed to determine the probable binding mode.
FeCl3-Catalyzed Combinatorial Synthesis of Functionalized Spiro[Indolo-3,10′-indeno [1,2- b ]quinolin]-trione Derivatives
Mondal, Animesh,Mukhopadhyay, Chhanda
supporting information, p. 404 - 408 (2016/01/15)
An efficient, inexpensive, environmentally friendly and high yield one-pot route to new spiro[indolo-3,10′-indeno [1,2-b]quinolin]-trione derivatives has been developed, involving three-component reaction of enaminones, N-substituted isatins and Indane-1,3-dione catalyzed by FeCl3. The approach to this spiro-heterocycle is noteworthy because it results in the formation of three new σ (two C-C and one C-N) bonds in a single operation, leading to the construction of novel spiro skeleton. This method works on a large scale in excellent yields.
Silica sulfuric acid-mediated synthesis of β-enaminones and β-enaminoesters under microwave irradiation
Datta, Bandita,Pasha
experimental part, p. 171 - 177 (2011/04/22)
Silica sulfuric acid, a heterogeneous reagent, has been found to be an efficient catalyst for the synthesis of β-enaminones and β-enaminoesters under microwave irradiation in a microwave reactor within 2 min. The experimental procedure is simple and environment-friendly, and results in excellent yields of the products. Further, the catalyst is recyclable, and the reaction is 60 times faster than the reaction at room temperature. Copyright Taylor & Francis Group, LLC.
Molecular iodine-catalyzed mild and effective synthesis of β-enaminones at room temperature
Datta, Bandita,Reddy, M. B. Madhusudana,Pasha
experimental part, p. 2331 - 2336 (2011/06/27)
Molecular iodine has been found to be an efficient and ecofriendly catalyst for the synthesis of β-enaminones from dimedone and amines at room temperature in the presence of acetonitrile within 60 min. The experimental procedure is simple, includes shorter reaction times, and results in excellent yields of the products. Copyright
NaHSO4/SiO2: An efficient catalyst for the synthesis of β-enaminones and 2-methylquinolin-4(1H)-ones under solvent-free condition
Sapkal, Suryakant B.,Shelke, Kiran F.,Shingate, Bapurao B.,Shingare, Murlidhar S.
experimental part, p. 723 - 726 (2011/03/19)
An efficient and simplified protocol for NaHSO4/SiO2 catalyzed solvent-free synthesis of β-enaminone and 2-methylquinolin-4(1H)- one derivatives under microwave irradiation is described. A series of functionalized derivatives have been synthesized in shorter reaction times with moderate to good yields. The use of milder catalyst in non-conventional method offers significant advantages over conventional methods, such as higher selectivities, simplicity, solvent-free reaction and non-environmental polluting conditions.
An improved method for the synthesis of carbazolones by palladium/copper-catalyzed intramolecular annulation of n -arylenaminones
Weng, Bojie,Liu, Rui,Li, Jing-Hua
experimental part, p. 2926 - 2930 (2010/10/18)
An improved method for the synthesis of carbazolones via the condensation of arylamines with 1,3-cyclodiketones followed by intramolecular oxidative cyclization catalyzed by palladium acetate and copper acetate in ethanol under an oxygen atmosphere was established. The improved method has the advantage of easily available starting materials and affords good yields.
Palladium-catalyzed coupling of vinylogous amides with aryl halides: Applications to the synthesis of heterocycles
Edmondson, Scott D.,Mastracchio, Anthony,Parmee, Emma R.
, p. 1109 - 1112 (2007/10/03)
Described herein is the first example of the palladium-catalyzed coupling of vinylogous amides with aryl bromides and chlorides. The scope of this reaction with respect to the aryl component is investigated. Additionally, a tandem reaction sequence in which the above coupling is followed by an intramolecular Heck reaction is presented. These reactions can be applied to high-yielding, one-pot syntheses of nitrogen-containing heterocycles.
