185945-75-9

Upstream product

• 34598-49-7 5-Bromo-1-indanone 
• 98-80-6 phenylboronic acid 
• 223692-69-1 5-phenyl-7-(trimethylsilyl)-1-indanone 
• 42348-86-7 5-chloro-1-indanone 
• 100-58-3 phenylmagnesium bromide 
• 3470-49-3 5-hydroxy-2,3-dihydro-1H-indene-1-one 
• 154122-32-4 1-oxo-2,3-dihydro-1H-inden-5-yl trifluoromethanesulfonate 

Downstream Products

• 211805-65-1 5-phenyl-1-indanol 
• 255895-84-2 2-bromo-5-phenylindan-1-one 

Relevant academic research and scientific papers

Inherent vs Apparent Chemoselectivity in the Kumada-Corriu Cross-Coupling Reaction

The Kumada-Corriu reaction is a powerful tool for C-C bond formation, but is seldom utilized due to perceived chemoselectivity issues. Herein, we demonstrate that high-yielding couplings can occur in the presence of many electrophilic and heterocyclic functional groups. Our strategy is mechanically based, matching oxidative addition rates with the rate of syringe pump addition of the Grignard reagent. The mechanistic reason for the effectiveness of this strategy is uncovered by continuous-infusion ESI-MS studies.

One-by-one hydrogenation, cross-coupling reaction, and Knoevenagel condensations catalyzed by PdCl2 and the downstream palladium residue

A novel catalyst-economic strategy with a recovered palladium catalyst was successfully applied for multi-task and maximum reuse in different types of one-by-one downstream reactions, from catalytic hydrogenation to Suzuki and Sonogashira-type cross-coupling reactions, Knoevenagel condensations, and trans-Knoevenagel-like condensations.

Heterogeneous Pd/C-catalyzed ligand-free, room-temperature suzuki-miyaura coupling reactions in aqueous media

A mild and efficient ligand-free Suzuki-Miyaura coupling reaction catalyzed by heterogeneous Pd/C was developed. Aryl bromides and triflates undergo the cross-coupling with aryl boronic acids in excellent yields without the presence of any additives in aqueous media at room temperature. Aryl vinyl boronic acids are also applicable to this coupling reaction and provide the trans-stilbene derivatives in high yields. The application of wet-type Pd/C to the coupling reaction was achieved without any loss of activity under aerobic conditions, and the reuse of Pd/C is feasible for a fifth run without significant loss of activity. Inductively coupled plasma (ICP) mass-spectrometric analysis of the filtrate from the reaction mixture of 4-bromonitrobenzene with phenylboronic acid demonstrated that the palladium metal hardly leached into the solution within the limits of the detector ( 1 ppm), thus suggesting that the present Suzuki-Miyaura reaction proceeded by heterogeneous catalysis.

Synthesis of indanones via solid-supported [2+2+2] cyclotrimerization

(Chemical Equation Presented) A new facile approach toward natural and unnatural indanones has been developed, featuring a solid-supported [2+2+2] cyclotrimerization as the key step. This strategy has been applied to the chemo- and regioselective assembly of indanone arrays and to the total synthesis of a recently isolated indanone marine natural product.

6-Aryl-8H-indeno[1,2-d]thiazol-2-ylamines: A1 adenosine receptor agonist allosteric enhancers having improved potency

Allosteric enhancers (AEs) of the A1 adenosine receptor (A 1AR) have potential as drugs for treating neurological, cardiovascular, and renal diseases. This report describes the synthesis and evaluation of a series of 6-aryl-8H-indeno[1,2-d]thiazol-2-ylamines that exhibited AE activity at the A1AR. Palladium-mediated condensation of arylboronic acids with 5-bromoindan-1-one generated arylindanones 2a-aj for iodine-catalyzed condensation with thiourea, generating 2-aminothiazolium salts 3a-aj. Binding studies using membranes from cells stably expressing human A 1ARs, A2AARs, or A3ARs evaluated AE activity and receptor subtype selectivity. The EC50 of the AE activities of compounds 3m-o, 3x, and 3ae were 2.2, 1.5, 0.9, 1.0, and 3.0 μM, respectively, substantially lower than that of the well characterized 2-amino-3-aroylthiophene (PD 81,723), >10 μM. The new compounds also have substantially higher maximal AE activity. These compounds had no AE activity at the A2AAR and only minimal activity at the A3AR. 2005 American Chemical Society.

Novel imidazolyl and triazolyl substituted biphenyl compounds: Synthesis and evaluation as nonsteroidal inhibitors of human 17α-Hydroxylase-C17, 20-lyase (P450 17)

The synthesis of a new series of P450 17 inhibitors is described. The imidazol-1-yl compounds 5 showed strong inhibition of P450 17 rat and especially human enzyme, the most active compounds being 5ax, 5ay and 5bx with IC50 values of 0.17, 0.24 and 0.25 μM, respectively (ketoconazole: 0.74 μM). The 1,2,4-triazol-1-yl compounds 6 were less active, while the 1,2,4-triazol-4-yl compounds 7 were inactive. The title compounds showed little inhibition of P450 arom. The most active P450 17 inhibitors 5ax and 5ay markedly decreased the testosterone plasma concentration of SD rats 2 h after application of 0.019 mmol/kg. After 6 h, 5ay still exhibited a strong effect. Copyright (C) 2000 Elsevier Science Ltd.

Polycyclic thiazolidin-2-ylidene amines, process for their preparation, and their use as pharmaceuticals

Polycyclic thiazolidin-2-ylidene amines and their physiologically tolerable salts and physiologically functional derivatives of the formula I in which the radicals have the meanings indicated, and their physiologically tolerable salts and a process for their preparation are described. The compounds are suitable, for example, as anorectics.