94839-07-3

Usage

Uses

Used in Pharmaceutical Synthesis:
3,4-METHYLENEDIOXYPHENYLBORONIC ACID is used as a key reactant in the synthesis of pharmaceutical compounds, particularly for the formation of complex organic molecules and heterocycles. Its reactivity and stability contribute to the efficient production of target compounds with desired biological activities.
Used in Organic Synthesis:
3,4-METHYLENEDIOXYPHENYLBORONIC ACID is used as a versatile reagent in organic synthesis for the formation of carbon-carbon and carbon-heteroatom bonds. Its applications include the Petasis reaction, Mannich-type multicomponent assembly, Suzuki-Miyaura cross-coupling, oxidative Heck reaction, and intramolecular Alder-ene and Pictet-Spengler reactions.
Used in the Petasis Reaction:
3,4-METHYLENEDIOXYPHENYLBORONIC ACID is used as a reactant in the Petasis reaction between glyoxylic acid, α-amino phosphonates, and organylboronic acids. This reaction allows for the formation of complex organic molecules with potential applications in various fields, including pharmaceuticals and materials science.
Used in Mannich-Type Multicomponent Assembly:
3,4-METHYLENEDIOXYPHENYLBORONIC ACID is used as a reactant in the Mannich-type multicomponent assembly and 1,3-dipolar cycloaddition for the synthesis of tetrahydroisoquinoline fused isoxazolidine scaffolds. This method enables the efficient construction of complex heterocyclic structures with potential applications in medicinal chemistry.
Used in Suzuki-Miyaura Cross-Coupling:
3,4-METHYLENEDIOXYPHENYLBORONIC ACID is used as a reactant in the Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides. This reaction is a powerful tool for the formation of carbon-carbon bonds, allowing for the synthesis of a wide range of organic compounds, including pharmaceuticals and natural products.
Used in Oxidative Heck Reaction:
3,4-METHYLENEDIOXYPHENYLBORONIC ACID is used as a reactant in the oxidative Heck reaction for the synthesis of functionalized cinnamaldehyde derivatives. This reaction provides a convenient method for the preparation of aldehydes with potential applications in the synthesis of biologically active compounds.
Used in Intramolecular Alder-Ene and Pictet-Spengler Reactions:
3,4-METHYLENEDIOXYPHENYLBORONIC ACID is used as a reactant in intramolecular Alder-ene and Pictet-Spengler reactions for the synthesis of crinine. These reactions are valuable for the construction of complex heterocyclic structures with potential applications in the development of pharmaceuticals and agrochemicals.

Upstream product

• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 121-43-7 Trimethyl borate 
• 274-09-9 Methylenedioxybenzene 
• 5419-55-6 Triisopropyl borate 
• 13675-18-8 tetrahydroxydiboron 
• 1682-37-7 3,4-(methylenedioxy)benzenediazonium tetrafluoroborate 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 688-74-4 boric acid tributyl ester 

Downstream Products

• 4791-89-3 3,3,3',4'-bis(methylenedioxy)biphenyl 
• 161196-32-3 methyl o-(3',4'-methylenedioxyphenyl)phenylcarbamate 
• 161196-37-8 methyl N-methyl-N-carbamate 
• 175883-24-6 5-[4,5-difluoro-2-[4-(methylsulfonyl)phenyl]phenyl]-1,3-benzodioxole 
• 565203-80-7 3-benzo[1,3]dioxol-5-yl-4-methoxy-benzonitrile 
• 74199-04-5 4,5,6-trimethoxy-3',4'-mehylendioxybiphenyl-2-carbaldehyde 
• 842170-41-6 5-benzo[1,3]dioxol-5-yl-nicotinic acid 
• 866454-84-4 (S)-6-(3,4-methylenedioxyphenyl)-1-nitrocyclohexene 
• 221006-72-0 1-[3',4'-(methylenedioxy)biphenyl-4-yl]ethanone 

Relevant academic research and scientific papers

Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source

In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions

Asymmetric conjugate addition of aryl halides or aryl triflates to electron-deficient olefins was realized by sequential Miyaura borylation and Hayashi-Miyaura conjugate addition in one pot. A nickel-catalyzed borylation of aryl halides or triflates and a rhodium-chiral diene complex catalyzed enantioselective conjugate addition was executed as a pair of relay reactions as a more efficient and greener protocol.

An efficient synthesis of 8-substituted Odoratine derivatives by the Suzuki coupling reaction

An efficient method for the preparation of 8-substituted odoratine [(3-(3 ′, 4 ′-methylenedioxyphenyl)-5,6,7-trimethoxyisoflavone] derivatives, structurally similar to glaziovianin A, a known cytotoxic substance, has been described.

Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts

We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.

An easy route to (hetero)arylboronic acids

An unprecedented spontaneous reactivity between diazonium salts and diboronic acid has been unveiled, leading to a versatile arylboronic acid synthesis directly from (hetero)arylamines. This fast reaction (35 min overall) tolerates a wide range of functional groups and is carried out under very mild conditions. The radical nature of the reaction mechanism has been investigated.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds of Formula IIa: and compositions thereof, and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Sequential one-pot access to molecular diversity through aniline aqueous borylation

On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

NOVEL PYRIMIDINE COMPOUNDS, PROCESS FOR THEIR PREPARATION AND COMPOSITIONS CONTAINING THEM

The present invention provides new heterocyclic compounds, particularly substituted pyrimidines, methods and compositions for making and using these heterocyclic compounds, and methods for treating a variety of diseases and disease states, including atherosclerosis, arthritis, restenosis, diabetic nephropathy, or dyslipidemia, or disease states mediated by the low expression of Perlecan.

INDOLES USEFUL IN THE TREATMENT OF INFLAMMATION

There is provided compounds of formula (I), Wherein X1 , R1 , R2 , R3, R4, R5 and R6 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a member of the MAPEG family is desired and/or required, and particularly in the treatment of inflammation.

Development of an Efficient Procedure for Indole Ring Synthesis from 2-Ethynylaniline Derivatives Catalyzed by Cu(II) Salts and Its Application to Natural Product Synthesis

The development of efficient methods for the indole synthesis catalyzed by Cu(II) salts and its applications were investigated. Cu(OAc)2 has been proved to be the best catalyst for the synthesis of various 1-p-tolylsulfonyl or 1-methylsulfonylindoles, which have both electron-withdrawing and electron-donating groups on the aromatic ring and C2 position of indoles. For the primary aniline derivatives, Cu(OCOCF 3)2 showed good activities, while Cu(OAc)2 was a good catalyst for the cyclization of secondary anilines. This methodology could be applied to the sequential cyclization reaction for the compounds which have the electrophilic part in the same molecule. By prior treatment with KH, the sequential cyclization was realized to provide the tricyclic ring systems, but it was limited to five- and six-membered rings for the second cyclization. Finally, formal and total synthesis of hippadine with the Cu(II)-promoted indole synthesis as the key step was accomplished.