271-95-4

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Benzisoxazole is used as a key component in the development of antiepileptic drugs, such as zonisamide, which is effective for the treatment of partial seizures. Its presence in the molecular structure of these drugs contributes to their therapeutic effects.
1,2-Benzisoxazole is also used as a substrate for rabbit liver aldehyde oxidase, an enzyme involved in the metabolism of various compounds, including drugs and xenobiotics. This application aids in the study of enzyme activity and the development of new pharmaceuticals.
Additionally, 1,2-Benzisoxazole is utilized in the production of 5-nitro-benzo[d]isoxazole, a compound with potential applications in the synthesis of other pharmaceuticals.
Used in Chemical Synthesis:
1,2-Benzisoxazole serves as a versatile building block in the synthesis of various organic compounds, including those with potential applications in the pharmaceutical, agrochemical, and materials science industries. Its unique structure and reactivity make it a valuable intermediate in the development of new molecules with diverse properties and functions.

InChI:InChI=1/C7H5NO/c1-2-4-7-6(3-1)5-8-9-7/h1-5H

Upstream product

• 90-02-8 salicylaldehyde 
• 59417-52-6 2-(acetoxyiminomethyl)phenol 
• 94-67-7 salicylaldehyde-oxime 
• 90368-32-4 2,2-dimethyl-1,3-dioxane-4,5,6-trione O-phenyloxime 
• 80277-94-7 hexanoylsalicylaldoxime 
• 144447-19-8 2-hydroxybenzaldehyde oxime hydrogen sulfate potassium salt 
• 76347-03-0 3-methyl-4-(O-phenyloximino)isoxazol-5(4H)-one 
• 13519-78-3 2-ethoxy-N-allylaniline 
• 15258-47-6 2-methoxy-N-allylaniline 
• 1483-72-3 diphenyliodonium chloride 
• 145508-94-7 tert-butyl 4-(iodomethyl)piperidine-1-carboxylate 
• 21013-96-7 (E)-2-hydroxylbenzaldehyde oxime 
• 80289-35-6 lauroylsalicylaldoxime 

Downstream Products

• 39055-82-8 5-acetyl-2-hydroxybenzonitrile 
• 611-20-1 salicylonitrile 
• 4481-51-0 2-((2-hydroxybenzylamino)methyl)phenol 
• 56394-87-7 3-(4-chloro-phenyl)-7-methyl-benzo[d]isoxazole 
• 1044822-20-9 methyl 2-phenyl-2H-benzo[e][1,3]oxazine-2-carboxylate 
• 1044822-21-0 C₂₅H₂₁NO₅ 
• 72332-14-0 2-cyanophenoxide ion 
• 489409-87-2 3-(5-nitro-biphenyl-2-yl)-benzo[d]isoxazole 

Relevant academic research and scientific papers

An efficient synthesis of oxazolines: Via a cascade reaction between azaoxyallyl cations and 1,2-benzisoxazoles

A formal [3 + 2] cycloaddition reaction between the C and O terminals of azaoxyallyl cations formed in situ and 1,2-benzisoxazoles has been realized. This one-pot cycloaddition method provided an effective and practical pathway to synthesize oxazoline in good yields under mild conditions. The title products exhibited unique fluorescence properties.

[3 + 2]-Cycloaddition of Azaoxyallyl Cations with 1,2-Benzisoxazoles: A Rapid Entry to Oxazolines

A novel and efficient [3 + 2] cycloaddition reaction of azaoxyallyl cations and 1,2-benzisoxazoles to give oxazoline derivatives has been developed. The transformation provides a rapid entry to functionalized oxazoline scaffolds under mild and transition-metal-free conditions, which will greatly expand the reaction types of heterocycle chemistry and pave the way for syntheses of bioactive compounds.

Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles

A Rh(II)-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with 2,1-benzisoxazoles has been developed, which affords an efficient method for the synthesis of quinazoline derivatives. The transformation represents an unprecedented example which utilizes N-sulfonyl-1,2,3-triazole as an aza-[2C]-component in cycloadditions. Meanwhile, a Rh(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with 1,2-benzisoxazoles is also presented, which enables the rapid synthesis of functionalized imidazole derivatives.

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

Chromatography-free entry to substituted salicylonitriles: Mitsunobu-triggered domino reactions of salicylaldoximes

A mild and efficient one-pot procedure is described to transform salicylaldoximes into salicylonitriles using Mitsunobu chemistry. The reactions proceed through the corresponding 1,2-benzisoxazoles that undergo the Kemp elimination in situ to generate the

Triflic anhydride: A mild reagent for highly efficient synthesis of 1,2-benzisoxazoles, isoxazolo, and isothiazolo quinolines without additive or base

The synthetic utility of trifluoromethanesulphonic anhydride (triflic anhydride, TA) without additive or base for the high-yielding synthesis of a wide variety of 1,2-benzisoxazoles from 2-hydroxyaryl aldoximes and ketoximes under mild conditions has been carried out for the first time. As a continuation of our study, syntheses of isoxazolo and isothiazolo quinolones have also been demonstrated using triflic anhydride under similar conditions. This method is simple and has benefits from the easy way to isolate the products in excellent yields.

Gallium-containing polymer brush film as efficient supported Lewis acid catalyst in a glass microreactor

Polystyrene sulfonate polymer brushes, grown on the interior of the microchannels in a microreactor, have been used for the anchoring of gallium as a Lewis acid catalyst. Initially, gallium-containing polymer brushes were grown on a flat silicon oxide surface and were characterized by FTIR, ellipsometry, and X-ray photoelectron spectroscopy (XPS). XPS revealed the presence of one gallium per 2-3 styrene sulfonate groups of the polymer brushes. The catalytic activity of the Lewis acid-functionalized brushes in a microreactor was demonstrated for the dehydration of oximes, using cinnamaldehyde oxime as a model substrate, and for the formation of oxazoles by ring closure of ortho-hydroxy oximes. The catalytic activity of the microreactor could be maintained by periodic reactivation by treatment with GaCl3.

Heterogeneous catalytic method for the conversion of aldoximes into nitriles using molecular sieve modified with Copper(II)

A simple heterogeneous metal-catalyzed method was developed for the transformation of aldoximes into nitriles. Molecular sieve (4 A) modified with copper(II) proved to be an efficient catalyst for the conversion. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Reaction of triflyl-imidazole with aldoximes: Facile synthesis of nitriles and formation of novel aldoxime-bis(N-triflyl)-imidazole adducts

The synthetic utility of N-triflylimidazole as an in situ reagent for facile, high yielding, synthesis of various aliphatic, aromatic, and heteroaromatic nitriles from the corresponding aldoximes has been demonstrated. With benzaldoximes, in the presence of certain substitutents (2-F; 2-OMe; 3-CF3; 2-Me-5-F) a different course of reaction was observed, leading instead to novel 1:1 aldoxime-bis(N-triflyl)imidazole covalent adducts, in which the aldoxime oxygen atom is bonded to the imidazole C-2 ring carbon. For these aldoximes, conversion to nitrile could be effected by reaction with Tf2O in the absence of imidazole. The molecular structure of the adduct formed from 2-methyl-5-fluoro-benzaldoxime was confirmed by X-ray analysis. Plausible mechanisms for the formation of 1:1 covalent adducts have been considered. Various attempts to isolate such adducts via the reaction of an authentic sample of bis(N-triflyl)imidazolium trifate with aldoxime were unsuccessful. Remarkably, whereas isolated benzaldoxime adducts undergo deprotonation/methylation with NaH/MeI, an authentic sample of bis(N-triflyl)imidazolium triflate did not undergo H/Me exchange under these conditions. These transformations are discussed.

ALKYL-SUBSTITUTED 3' COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, Ar, m and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.