267-54-9

Usage

Uses

Used in Pharmaceutical Industry:
[1,3]Dioxolo[4,5-f]-2,1-benzisoxazole(8CI,9CI) is used as a potential active pharmaceutical ingredient (API) for its possible medicinal properties. [1,3]Dioxolo[4,5-f]-2,1-benzisoxazole(8CI,9CI)'s unique structure may contribute to its effectiveness in treating various conditions, such as inflammation or pain.
Used in Research and Development:
In the field of medicinal chemistry, [1,3]Dioxolo[4,5-f]-2,1-benzisoxazole(8CI,9CI) serves as a valuable compound for research and development. Scientists and researchers can use [1,3]Dioxolo[4,5-f]-2,1-benzisoxazole(8CI,9CI) to study its properties, interactions with biological systems, and potential applications in drug discovery and design.
Used in Drug Synthesis:
[1,3]Dioxolo[4,5-f]-2,1-benzisoxazole(8CI,9CI) may also be used as a key intermediate or building block in the synthesis of more complex pharmaceutical compounds. Its unique structure can be exploited to create novel drugs with improved efficacy, safety, or other desirable characteristics.

InChI:InChI=1/C8H5NO3/c1-5-3-12-9-6(5)2-8-7(1)10-4-11-8/h1-3H,4H2

Upstream product

• 712-97-0 6-nitro-1,3-benzodioxole-5-carbaldehyde 
• 138306-34-0 [1-(6-Nitro-benzo[1,3]dioxol-5-yl)-meth-(E)-ylidene]-phenyl-amine 
• 1080661-03-5 N-[(E)-(6-nitro-1,3-benzodioxol-5-yl)methylene]aniline 

Downstream Products

• 97417-59-9 7-phenyl-[1,3]dioxolo[4,5-g]quinolin-6(5H)-one 
• 20332-16-5 4,5-methylenedioxyanthranilic acid 

Relevant academic research and scientific papers

Palladium-catalyzed carbonylative cyclization of benzyl chlorides with anthranils for the synthesis of 3-arylquinolin-2(1: H)-ones

An efficient carbonylative procedure for the synthesis of 3-arylquinoin-2(1H)-ones has been established. Through a palladium-catalyzed aminocarbonylation of benzyl chlorides with anthranils, a variety of 3-arylquinoin-2(1H)-one products were obtained in moderate to excellent yields with good functional group tolerance. This journal is

Access to acridones by tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation of anthranils with arylboronic acids

An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance. What's more, a possible mechanistic proposal was also presented.

I2-DMSO mediated oxidative amidation of methyl ketones with anthranils for the synthesis of: α -ketoamides

An I2-DMSO mediated oxidative amidation of methyl ketones using anthranils as masked N-nucleophiles has been developed for the direct synthesis of α-ketoamides with high atom-economy. This metal-free process involves reductive N-O bond cleavage of anthranils and oxidative C-N bond formation of methyl ketones under mild conditions. The iodo group and electrophilic formyl group provide multiple possibilities for further functionalization of α-ketoamides.

Rh(iii)-Catalyzed tandem indole C4-arylamination/annulation with anthranils: Access to indoloquinolines and their application in photophysical studies

An efficient Rh(iii)-catalyzed straightforward strategy was developed for the tandem C4 arylamination/annulation of indole derivatives with anthranil to provide indoloquinoline moieties. This method is simple and regioselective with a wide scope and functional group tolerance. Mechanistic studies revealed the important role of the newly installed azacycle in the conversion of O-protected aldoximes to their cyano derivatives. Studies were carried out to explore the promising photophysical properties of the obtained indoloquinoline derivatives.

Gold-Catalyzed Intermolecular Formal [4 + 2 + 2]-Cycloaddition of Anthranils with Allenamides

The construction of eight-membered rings is a challenging issue due to unfavorable transannular strain and entropic barriers. We report herein a gold-catalyzed formal [4 + 2 + 2] cycloaddition reaction of anthranils with allenamides to deliver oxa-bridged eight-membered heterocycles in accepted yields with unique E/Z configuration. Moreover, the asymmetric [4 + 2 + 2] cycloaddition by using chiral phosphoramidite gold catalyst has also been conducted.

Copper-catalyzed coupling of anthranils and α-keto acids: Direct synthesis of α-ketoamides

Copper-catalyzed coupling of α-keto acids with anthranils is reported for the synthesis of α-ketoamides. This process involves N-O/C-O bond cleavages and C-N bond formation. Furthermore, the decarboxylation of α-keto acids can be successfully suppressed under redox-neutral conditions.

RhIII-Catalyzed Straightforward Synthesis of Benzophenanthroline and Benzophenanthrolinone Derivatives using Anthranils

An efficient pot-economic and step-economic RhIII-catalyzed site-selective direct amination/annulation strategy was developed for the synthesis of benzophenanthroline derivatives using quinoline N-oxides and anthranils. The method was further extended to the synthesis of nitrogen-containing extended π-conjugated benzophenanthrolinone derivatives. Late-stage functionalizations of cinchonidine and cinchophen derivatives and synthesis of a bioactive quinolino-indole were achieved.

Gold-Catalyzed Annulations of N-Propargyl Ynamides with Anthranils with Two Distinct Chemoselectivities

Gold-catalyzed annulation of N-propargyl ynamides with anthranils can proceed by two distinct mechanisms. In the case of a terminal N-propargyl ynamide, its resulting α-imino gold carbene reacts with a tethered alkyne to generate a vinyl cation to enable hydrolysis, which ultimately yields a pyrrolo[2,3-b]quinoline derivative after treatment with p-toluenesulfonic acid. For an internal alkyne, its α-imino gold carbene reacts with a tethered alkyne via either a vinyl cation or an alkenylgold carbene; both paths ultimately lead to a 4-ketone-2-aminopyrrole derivative. Our mechanistic analysis indicates that water is a better nucleophile than anthranil for terminal ynamides, whereas water and anthranils are equally reactive for internal ynamides.

Cu(II)/Ag(I)-Catalyzed Cascade Reaction of Sulfonylhydrazone with Anthranils: Synthesis of 2-Aryl-3-sulfonyl Substituted Quinoline Derivatives

In this paper, a Cu(II)/Ag(I)-catalyzed cascade reaction of anthranils with sulfonylhydrazone to construct 2-phenyl-3-sulfonyl disubstituted quinoline derivatives under mild conditions was studied. The mechanism study indicated that this reaction involves radical addition, and new C-C, C-N, and C-S bonds were constructed in one step.

Gold(III)-Catalyzed Site-Selective and Divergent Synthesis of 2-Aminopyrroles and Quinoline-Based Polyazaheterocycles

A facile, site-selective, and divergent approach to construct 2-aminopyrroles and quinoline-fused polyazaheterocycles enabled by a simple gold(III) catalyst from ynamides and anthranils under mild reaction conditions is described. This one-pot strategy uses readily available starting materials, proceeds in a highly step- and atom-economical manner, with broad substrate scope and scale-up potential. The key element for success in this tandem reaction is a catalyst-directed preferred quenching of the in situ generated gold carbene intermediates by a nucleophilic benzyl/2-furylmethyl moiety on the ynamides as an alternative to the known C?H annulation leading to indoles.