873-67-6

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 2468, 1988 DOI: 10.1021/jo00246a014

InChI:InChI=1/C7H5NO/c9-8-6-7-4-2-1-3-5-7/h1-5H

Upstream product

• 13591-33-8 benzonitrolic acid 
• 698-16-8 benzohydroximoyl chloride 
• 10266-71-4 N-?hydroxybenzenecarboximidoyl bromide 
• 76016-69-8 3-nitro-4-phenyl-1,2,5-oxadiazole 2-oxide 
• 109057-79-6 trityl phenylcyanomethane nitronate 
• 698-16-8 benzhydroximic acid chloride 
• 934-16-7 phenylhydroxamoyl chloride 
• 7707-64-4 3-phenyl-furazan 5-oxide 
• 7732-18-5 water 
• 1821-34-7 N-chlorobenzamide 
• 495-18-1 Benzohydroxamic acid 
• 263888-04-6 O-tert-butyldiphenylsilyl benzhydroxamate 
• 100-52-7 benzaldehyde 
• 15256-68-5 2,4,5-triphenyl-2H-1,2,3-triazole 1-oxide 

Downstream Products

• 55367-28-7 5-(furan-2-yl)-3-phenyl-4,5-dihydroisoxazole 
• 55124-75-9 3-phenyl-4,5-dihydro-isoxazole-4r,5c-dicarboxylic acid anhydride 
• 58598-96-2 5-(2’-pyridyl)-3-phenyl-1,2,4-oxadiazole 
• 4894-23-9 3,5-diphenyl-4,5-dihydro-isoxazole 
• 2157-50-8 propiophenone oxime 
• 5585-14-8 3,4-diphenyl-furazan 2-oxide 
• 103-71-9 phenyl isocyanate 
• 72418-40-7 3-phenylisoxazole-5-carbaldehyde 
• 93979-32-9 5-benzyl-3-phenyl-2-Δ²-isoxazoline 
• 20821-97-0 5-(4-methoxyphenyl)-3-phenyl-4,5-dihydroisoxazole 
• 5050-64-6 3,5,5-triphenyl-4,5-dihydroisoxazole 
• 613-91-2 acetophenone oxime 
• 100-47-0 benzonitrile 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

AOT-based microemulsions accelerate the 1,3-cycloaddition of benzonitrile oxide to N-ethylmaleimide

We studied the 1,3-dipolar cycloaddition of benzonitrile oxide to N-ethylmaleimide in AOT/isooctane/water microemulsions at 25.0 °C and found the reaction rate to be roughly 150 and 35 times greater than that in isooctane and pure water, respectively. The

New approaches to the synthesis of canthin-4-one alkaloids and synthetic analogues

Two novel approaches to the canthin-4-one ring system have been worked out. Claisen-type condensation of 1-acetyl-β-carboline with N-acyl benzotriazoles gives, via intermediate 1,3-diketones, 6-alkylcanthin-4-ones in one single operation, but this protocol is restricted to small alkyl substituents. An alternative approach, via 1-ethynyl-β-carboline and 1-isoxazolyl-β-carbolines, followed by reductive isoxazole cleavage and cyclization, is more versatile. 5,6-disubstituted canthin-4-ones are accessible via iodination at C-5 and subsequent Pd-catalyzed cross-coupling.

Ionic liquids: Just molten salts after all?

While there has been much effort in recent years to characterise ionic liquids in terms of parameters that are well described for molecular solvents, using these to explain reaction outcomes remains problematic. Herein we propose that many reaction outcom

Pseudo-Interphase of Liposome Promotes 1,3-Dipolar Cycloaddition Reaction of Benzonitrile Oxide and N -Ethylmaleimide in Aqueous Solution

The hydrophobic interior of a liposome membrane was used as a platform for the organic synthesis of hydrophobic compounds in water. The 1,3-dipolar cycloaddition of benzonitrile oxide (BNO) and N-ethylmaleimide (EMI) in liposome suspensions was carried ou

Synthesis of 2-(12-aryldodecanoyl)cyclohexane-1,3-diones

Synthesis was developed of 2-(10-undecenoyl)cyclohexane-1,3-diones containing in the side chain keto and hydroxy groups and a phenyl substituent. The synthesis is underlain by a nitrile oxide approach. The scheme included isoxazole synthesis for the prote

Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

Regioselective [3+2] cycloaddition of nitrile oxides to 1Н-pyrrole-2,3-diones: synthesis of spiro[pyrroledioxazoles]

[Figure not available: see fulltext.] 1,3-Dipolar cycloaddition of 1H-pyrrole-2,3-diones to nitrile oxides generated in situ from N-hydroxybenzimidoyl chlorides by the action of triethylamine proceeds regioselectively with the formation of 1,4,2-dioxazole

One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies

Abstract: Regioselective synthesis of some novel 7-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one linked isoxazole hybrids via copper(I) catalyzed one-pot reaction of various aromatic aldehydes with 7-bromo-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one was developed. The structures of the compounds that are synthesized are confirmed by 1H NMR, 13C NMR, and mass spectra. All the hybrids have been tested for their in vitro anticancer activity against four human cancer cell lines, including HeLa, MCF-7, A549, and PC3. Three of the compounds exhibited remarkable anticancer activity compared to standard drug etoposide. Molecular docking studies with EGFR also strengthened the in vitro anticancer activity.

One-pot synthesis of novel ether-linked diisoxazole derivatives via sequential O-propargylation and 1,3-dipolar cycloaddition from 2-bromohomoallylic alcohols

A simple and efficient, one-pot approach for the synthesis of ether-linked diisoxazole derivatives has been developed through sequential reactions, which includes O-propargylation of 2-bromohomoallylic alcohols with propargyl bromide in the presence of so

Reactions of 1,2,4-Oxadiazole[4,5-a]piridinium Salts with Alcohols: the Synthesis of Alkoxybutadienyl 1,2,4-Oxadiazoles

1,2,4-Oxadiazole[4,5-a]piridinium salts add alcohols and alkoxides to undergo electrocyclic ring opening affording alkoxybutadienyl 1,2,4-oxadiazole derivatives. The pyridinium salts represent a special class of Zincke salts that are prone to rearrange to give alkoxybutadienyl 1,2,4-oxadiazoles when treated with suitable nucleophiles or, alternatively, to give pyridones in the presence of bicarbonate. The pivotal tuning of the experimental conditions leads to a straightforward synthesis of valuable 1,2,4-oxadiazole derivatives. The mechanism is also discussed in the light of previous observations.