17666-95-4

Upstream product

• 17666-97-6 5-Methoxy-1,3-dioxo-indan-2-carboxylic acid ethyl ester 
• 100-07-2 4-methoxy-benzoyl chloride 
• 1663-67-8 malonoyl dichloride 
• 148502-18-5 5-methoxy-1-oxoindan-3-ylammonium chloride 
• 908128-22-3 7-methoxy-1,4-dioxo-3-(phenyliodonio)-1,4-dihydronaphthalen-2-olate 
• 100-09-4 4-methoxybenzoic acid 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 

Downstream Products

• 106507-42-0 2,2-dihydroxy-5-methoxyindane-1,3-dione 
• 507484-59-5 2-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile 
• 17828-67-0 5-methoxy-2-phenyl-1H-indene-1,3(2H)-dione 

Relevant academic research and scientific papers

Sulfoximines Assisted Rh(III)-Catalyzed C-H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines

A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh(III)-catalyzed C-H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.

Subtle side-chain tuning on terminal groups of small molecule electron acceptors for efficient fullerene-free polymer solar cells

Four dithienoindaceno[1,2-b:5,6-b′]dithiophene (DT-IDT) based small molecules IT-O1, IT-O2, IT-O3 and IT-O4 with increasing alkoxyl chain length from methoxy to butoxy on the terminal-groups were synthesized to investigate the end-group side-chain effects on these acceptor-donor-acceptor-type small molecule electron acceptors. The optical absorption and energy levels of the four molecules, blend morphologies, carrier mobilities, and photovoltaic performances of the devices blended with the polymer PBDB-T are systematically investigated. Interestingly, both the solubility and electron mobility are enhanced for these materials with decrease in side chain length, which lead to ideal morphologies and balanced charge transport. Hence, increased Jsc and FF, and thus distinctly higher PCEs of 11.6% were obtained from the PBDB-T:IT-O1-based devices.

Synthetic methods for the preparation of ARQ 501 (β-Lapachone) human blood metabolites

ARQ 501 (3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b] pyran-5,6-dione), a synthetic version of β-Lapachone, is a promising anti-cancer agent currently in multiple Phase II clinical trials. Promising anti-cancer activity was observed in Phase I and Phase II trials. Metabolism by red blood cells of drugs is an understudied area of research and the metabolites arising from oxidative ring opening (M2 and M3), decarbonylation/ring contraction (M5), and decarbonylation/oxidation (M4 and M6) of ARQ 501 offer a unique opportunity to provide insight into these metabolic processes. Since these metabolites were not detected in in vitro incubations of ARQ 501 with liver microsomes and were structurally diverse, confirmation by chemical synthesis was considered essential. In this report, we disclose the synthetic routes employed and the characterization of the reference standards for these blood metabolites as well as additional postulated structures, which were not confirmed as metabolites.

A convenient route to indane-1,3-diones and 3-hydroxyindan-1-ones

The synthesis of alkoxyindane-1,3-diones is described in four steps starting from benzaldehydes via 3-amino and 3-hydroxyindan-1-ones. Key Words: indane-1,3-diones / 3-hydroxyindan-1-ones / diazotization / oxidation

Acylation of Aroyl Chlorides via a Template Friedel-Crafts Process: Synthesis of Indan-1,3-diones

Variously substituted indan-1,3-diones have been regioselectively prepared in a one-pot synthesis by sequential cross-condensation-cycloacylation of aromatic acyl chlorides and acetyl chloride or malonyl dichloride, electrophilic acylation of aromatic acyl chlorides representing the key step in the process.The synergism of the aromatic carbonyl enolization and the organization of the reacting system promoted by the metal is emphasized to account for the mild reaction conditions.

Synthetic routes to ninhydrins. Preparation of ninhydrin, 5-methoxyninhydrin, and 5-(methylthio)ninhydrin

Two syntheses of 5-methoxyninhydrin (2,2-dihydroxy-5-methoxy-1,3-indanedione) are described. One method employs a novel and efficient two step route, which begins with commercially available 6-methoxy-1-indanone. The application of this strategy for the preparation of a new ninhydrin derivative, 5-(methylthio)ninhydrin, and ninhydrin is also presented.