27271-35-8

Upstream product

• 698-16-8 benzohydroximoyl chloride 
• 95-13-6 1-indene 
• 100-52-7 benzaldehyde 
• 932-90-1 Benzaldoxime 
• 873-67-6 benzonitrile oxide 

Downstream Products

• 5657-78-3 5,6A,7,11b-tetrahydro-indeno[2,1-c]quinolin-6-one 
• 33982-86-4 (2,3-dihydro-1H-inden-2-yl)(phenyl)methanone 
• 16565-63-2 2-Benzimidoyl-indanon-⁽¹⁾ 
• 16565-60-9 3-phenyl-4H-indeno[2,1-d]isoxazole 

Relevant academic research and scientific papers

Water-Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4-Oxadiazoles

Conventional methods generate nitrile oxides from oxime halides in organic solvents under basic conditions. However, the present work revealed that water-assisted generation of nitrile oxides proceeds under mild acidic conditions (pH 4-5). Cycloadditions of nitrile oxides with alkynes and alkenes easily occurred in water without using catalysts, thus yielding isoxazoles and isoxazolines, respectively, with excellent stereoselectivity toward five- and six-membered cyclic alkenes. A double stereoselective cycloaddition of two units of a nitrile oxide with cyclohexene was also achieved, thus yielding 1,2,4-oxadiazole derivatives having a unique hybrid isoxazoline-oxadiazole skeleton. Enantiomerically pure isoxazolines were prepared from monoterpenes with a ring strain. In one case, the isoxazoline with a butterfly-like structure was simply prepared, and it might be used as a ligand in asymmetric catalysis.

One-pot synthesis of isoxazolines from aldehydes catalyzed by iodobenzene

A convenient one-pot, three-step procedure for the synthesis of isoxazolines starting from aldehydes has been developed involving catalytic cycloaddition between nitrile oxides and alkenes, in which iodobenzene is used as the catalyst for the in situ generation of a hypervalent iodine intermediate. In this approach, the aldehydes are first transformed with hydroxylamine sulfate into aldoximes, which are then oxidized to nitrile oxides by the in situ generated hypervalent iodine intermediate; finally, a 1,3-dipolar cycloaddition between the nitrile oxides and alkenes occurs to provide the isoxazolines in moderate to good yields.

Hypervalent iodine-catalyzed cycloaddition of nitrile oxides to alkenes

A new and convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was fi