114977-17-2

Upstream product

• 100-42-5 styrene 
• 1875-48-5 N-aminophthalamide 
• 292638-85-8 acrylic acid methyl ester 
• 37802-08-7 1a-acetyl-1-phthalimidoamino-1a,6b-dihydro-1H-benzofuro<2,3-b>azirine 
• 134965-34-7 1-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1,1a-dihydro-6-oxa-1-aza-cyclopropa[a]indene-6a-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Aziridination of Alkenes using 3-Acetoxyaminoquinazolin-4-(3H)ones in the Presence of Tertiary Amines: Evidence for an Azaimide (N-Nitrene) Intermediate

Solutions of the triethylammonium imide 8, formed from triethylamine and 3-acetoxyaminoquinazolinone 4, react with alkenes at -30 deg C to give aziridines; the reactivity of the aziridinating intermediate is consistent with its formulation as an azaimide (N-nitrene).

Aryl iodide mediated aziridination of alkenes

(Chemical Equation Presented) Aryl iodide mediated aziridination of a variety of alkenes with N-aminophthalimide under mild conditions (m-CPBA, K 2CO3, CH2Cl2, 25°C) was achieved in moderate to good yields (up to 94%). By recovering the aryl iodide, a recyclable system is developed with product yield over 79% attained for the aziridination of trans-1,2-diphenylethylene.

Metal-free synthesis of 1,2-amino alcohols by one-pot olefin aziridination and acid ring-opening

A one-pot, two-step reaction comprising olefin aziridination and ring-opening of an aziridine intermediate to synthesize 1,2-amino alcohols has been developed. This reaction is suitable for several types of olefin. This methodology allows an efficient and

Electrocatalytic aziridination of alkenes mediated by n -Bu4NI: A radical pathway

Efficient electrocatalytic aziridination of alkenes has been achieved for the first time. A structurally broad range of aziridines was easily accessed using an undivided cell operated at constant current and mediated by a catalytic quantity of n-Bu4

Sodium-iodoxybenzoate mediated highly chemoselective aziridination of olefins

Herein we utilized, for the first time, sodium 2-iodoxybenzoate as a highly specific oxidant for PhthNH2 to create a highly chemoselective aziridination reagent. This method efficiently effects aziridination of electron-rich, electron-deficient, allylic alcohol and alkenyl bromide C=C bonds in good to excellent yields. Inter and intramolecular chemoselectivity was demonstrated between electron-rich and electron-deficient alkenes by using this efficient and metal free protocol.

Hypoiodite-mediated metal-free catalytic aziridination of alkenes

Look, no metal: A metal-free catalytic procedure for aziridination of alkenes using tetrabutylammonium iodide as the catalyst, m-chloroperoxybenzoic acid (mCPBA) as the terminal oxidant, and N-aminophthalimide as the nitrenium precursor has been developed (see scheme; right: X-ray structure of one of the products). Control experiments suggests that the active oxidant is in situ generated hypoiodous acid (HIO). Copyright

Superoxide-mediated synthesis of N-aminoaziridines from N-aminoheterocycles and olefins

Oxidation of 3-amino-2-methyl-4(3H)-quinazolone and N-aminophthalimide by superoxide ion generated in situ in the presence of olefinic substrates gives rise to the formation of N-aminoaziridine derivatives. Copyright Taylor & Francis, Inc.

Aziridination of alkenes with N-substituted hydrazines mediated by iodobenzene diacetate

Aziridination of a variety of alkenes with N-substituted hydrazines mediated by iodobenzene diacetate under mild conditions (K2CO 3, CH2Cl2) and ambient temperature were achieved in good to excellent yields (up to 99%), and conversions. The practicality and simplicity of this C-N bond formation protocol was exemplified by its application to the aziridination of cholesteryl acetate in a stereoselective manner.

Evidence for Phthalimidonitrene as a Common Intermediate in Several Extrusion Reactions

A common intermediate, presumably phthalimidonitrene 1, is generated in the thermolysis of the aziridinobenzofurans 3 (R = Ac, CO2Me, Bz, COBut and CN) as well as the sulphimide 4, and the azabenzonorbornadiene 5.The transfer of 1 shown in Scheme 1 is zero order in 2-acetylbenzofuran providing further evidence against a concerted bimolecular mechanism 10 for 'nitrene' transfer.

AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES: EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES

Oxidation of 3-aminoquinazolones e.g. (22) with lead tetra-acetate at -20 deg C gives N-acetoxyaminoquinazolones e.g. (23) which are stable in solution at this temperature.These N-acetoxyaminoquinazolones function as inter- and intramolecular aziridinating agents for alkenes and appear to be playing the role previously ascribed to the corresponding N-nitrenes.An analogous N-acetoxyaminophthalimide intermediate (31) is implicated in the lead tetra-acetate oxidation of N-aminophthalimide (4).