73721-00-3

Upstream product

• 256530-40-2 1-methyl-3-phenylindene ozonide 
• 22360-62-9 1-methyl-3-phenylindene 
• 28269-50-3 2-vinylbenzoic acid chloride 
• 27326-43-8 2-vinylbenzoic acid 
• 2039-88-5 2-bromostyrene 
• 124-38-9 carbon dioxide 
• 22679-42-1 2-ethylbenzophenone 
• 100-58-3 phenylmagnesium bromide 
• 84847-60-9 endo-1-methyl-3-phenylindene ozonide 
• 84810-14-0 exo-1-methyl-3-phenylindene ozonide 

Downstream Products

• 36192-86-6 o-Benzyl-hydratropasaeure 

Relevant academic research and scientific papers

Synthesis of Tofisopam by Way of Photoinduced CO2 Fixation

Herein reported is a unique synthetic route of Tofisopam, an anxiolytic drug containing a 2,3-benzodiazepine core structure. 3,4-Dimethoxypropylbenzene and 3,4-dimethoxybenzoic acid, which are both of plant origin, and CO2 constitute its carbon skeleton. These three renewable substances are united by two C?C bond forming reactions, i.e., a Friedel–Crafts acylation reaction and a photoinduced carboxylation reaction to construct the major carbon framework. Finally, a methyl group is introduced by a Kumada-type cross-coupling reaction to furnish Tofisopam. Various analogs of Tofisopam are readily synthesized by introducing other substituents than a methyl group at the last C?C bond forming step.

Rhodium-Catalyzed Hydrocarboxylation of Olefins with Carbon Dioxide

The catalytic hydrocarboxylation of styrenes derivatives and α,β-unsaturated carbonyl compounds with CO2(101.3 kPa) in the presence of an air-stable rhodium catalyst was explored. The combination of [RhCl(cod)]2(cod = cyclooctadiene) as a catalyst and diethylzinc as a hydride source allowed for effective hydrocarboxylation and provided the corresponding α-aryl carboxylic acids in moderate to excellent yields. In this catalytic process with carbon dioxide, intervention of the RhI–H species, which could be generated from the RhIcatalyst and diethylzinc, was clarified. Significantly, the catalytic asymmetric hydrocarboxylation of α,β-unsaturated esters with carbon dioxide was also performed by employing a cationic rhodium complex possessing (S)-(–)-4,4′-bi-1,3-benzodioxole-5,5′-diylbis(diphenylphosphine) [(S)-SEGPHOS] as a chiral diphosphine ligand. A plausible model for asymmetric induction was proposed by determination of the absolute configuration of the product.

Light-Driven Carboxylation of o-Alkylphenyl Ketones with CO2

o-Alkylphenyl ketones undergo a C-C bond forming carboxylation reaction with CO2 simply upon irradiation with UV light or even solar light. The reaction presents a clean process exploiting light energy as the driving force for carboxylation of organic molecules with CO2.

Diels-alder reactions of l,1-Bis(methylthio)ethene with pyran-2-ones

Bis(methylthio)ethene has been shown to undergo Diels-Alder cycloaddition reactions with a range of simple and aryl-fused pyran-2-ones. These reactions can be brought about under either high-temperature or high-pressure conditions. These reactions are all

Synthesis, X-ray Analysis, and Acidolysis of exo- and endo-1-Methylindene Ozonides

Ozonolyses of 2,3-disubstituted 1-methylindenes gave mixtures of the corresponding exo and endo ozonides.The structures of endo-1-methyl-3-phenylindene ozonide (3a) and exo-1-methyl-2,3-diphenylindene ozonide (2b) were determined by the X-ray analysis.Acidolysis of exo- and endo-1-methylindene ozonides 2a-d and 3a-d under several conditions revealed some characteristic features. (a) Antimony pentachloride or chlorosulfonic acid catalyzed the interconversion of the exo-endo ozonide isomers, the ratio in equilibrium being ca. 7:3 for all the pairs. (b) In the reaction of 3-methyl-substituted indene ozonides 2c,d and 3c,d in acetic-d3 acid-d a rapid hydrogen-deuterium exchange on the bridgehead methyl was observed. (c) In methylene chloride or acetic acid the ozonides decomposed very slowly, yielding the mixtures of rearranged products 4 and 5, carboxylic acid 6, and diketone 7; both the rate of decomposition and the product distribution being a marked function of the structure of the ozonides. (d) Methanol accelerated the decomposition of ozonides, the disappearance following pseudo-first-order kinetics.The rate decreased in the order 3a > 2a > 2b > 2c ca. 3c > 3b.This order was significantly different from the order observed in the reaction in acetic acid: 3b > 3c > 2b > 2c > 3a > 2a. (e) Reduction by AlHCl2 gave a mixture of 3,4-dihydro-1H-2-benzopyrans 19 - 22, the composition being significantly varied depending on the stereochemistry of the ozonides. (f) Treatment of 2a or 3a with bis(α-hydroxy-4-methylbenzyl)peroxide (31) gave two stereoisomeric peroxides 32a and 33a in roughly equal amounts.In contrast, the reaction of an exo ozonide 2d with a mixture of p-tolualdehyde and 30percent H2O2 (an equivalent of 31) afforded exclusively the corresponding exo peroxide 32d, while the endo isomer 3d gave predominantly the endo peroxide 33d.

2-(Arylmethyl)arylacetic Acids as Potential Antiinflammatory Agents

The title compounds 2 have been synthesized and tested for antiinflammatory activity.The synthetic method, consisting of the chemical sequence 3-aryl-1H-indenes (4) 2-(aroyl)arylacetic acids (5) 2, appears to be of value because of its simplicity