37716-10-2

Upstream product

• 780-25-6 N-benzylidene benzylamine 
• 698-16-8 benzohydroximoyl chloride 
• 622-42-4 1-nitro-1-phenylmethane 
• 934-16-7 phenylhydroxamoyl chloride 
• 932-90-1 Benzaldoxime 

Downstream Products

• 1485-70-7 N-benzylbenzamide 
• 888-71-1 3,5-diphenyl-1,2,4-oxadiazole 
• 19857-37-5 3-benzyl-2-phenyl-3,4-dihydroquinazolin-4-one 

Relevant academic research and scientific papers

Generation of N-Centered Radicals via a Photocatalytic Energy Transfer: Remote Double Functionalization of Arenes Facilitated by Singlet Oxygen

An unprecedented approach to the generation of an N-centered radical via a photocatalytic energy-transfer process from readily available heterocyclic precursors is reported, which is distinctive of the previous electron transfer approaches. In combination with singlet oxygen, the in-situ-generated nitrogen radical from the oxadiazoline substrate in the presence of fac-Ir(ppy)3 undergoes a selective ipso addition to arenes to furnish remotely double-functionalized spiro-azalactam products. The mechanistic studies provide compelling evidence that the catalytic cycle selects the energy-transfer pathway. A concurrent activation of molecular oxygen to generate singlet oxygen by energy transfer is also rationalized. Furthermore, the occurrence of the electron transfer phenomenon is excluded on the basis of the negative driving forces for one-electron transfer between oxadiazoline and the excited state of fac-Ir(ppy)3 with a consideration of their redox potentials. The necessity of singlet oxygen as well as the photoactivated oxadiazoline substrate is clearly supported by a series of controlled experiments. Density functional studies have also been carried out to support these observations. The scope of substrates is explored by synthesizing diversely functionalized cyclohexadienone moieties in view of their utility in complex organic syntheses and as potential targets in pharmacology.

Gold-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with 4,5-Dihydro-1,2,4-oxadiazoles: Synthesis of Functionalized 4-Aminoimidazoles

A gold-catalyzed formal [3 + 2] cycloaddition of ynamides with 4,5-dihydro-1,2,4-oxadiazoles has been developed. The reaction provides a concise and regioselective access to highly functionalized 4-aminoimidazoles likely via the formation of an α-imino go

Oxidative radical skeletal rearrangement induced by molecular oxygen: Synthesis of quinazolinones

Oxidative skeletal rearrangement of 5-aryl-4,5-dihydro-1,2,4-oxadiazoles into quinazolinones is induced by molecular oxygen (under a dry air atmosphere) that likely proceeds via transient iminyl radical species. Concise syntheses of biologically active qu

Base-induced cycloreversion of nitrile oxide cycloadducts: Conversion of imines into secondary and tertiary amides and aromatic aldehydes into acids without a conventional oxidising agent

A series of substituted Δ2-1,2,4-oxadiazolines (4,5-dihydro-1,2,4-oxadiazoles) 12 have been prepared by 1,3-dipolar cycloaddition of nitrile oxides to imines and are found, upon treatment with KOBut, to undergo cycloreversion to give nitriles and amide anions. These can be protonated to give secondary amides or treated in situ with alkyl halides to give tertiary amides in moderate to good overall yield, although the reaction is restricted to examples with an aromatic substituent at the 5-position. The 1,4,2-dioxazoles 15, formed by cycloaddition of benzonitrile oxide to aromatic aldehydes, similarly undergo cycloreversion allowing direct conversion either into substituted benzoic acids or their methyl esters. Copyright 1996 by the Royal Society of Chemistry.