896905-07-0

Upstream product

• 7147-44-6 1-(2-chlorophenyl)ethanone oxime 
• 108-24-7 acetic anhydride 
• 2142-68-9 1-(2-chlorophenyl)ethanone 

Downstream Products

• 1612759-96-2 (Z)-1-(2-chlorophenyl)-2-tosylethenamine 
• 419557-34-9 2-(2-chlorophenyl)imidazo[1,2-a]pyridine 
• 1519051-01-4 N'-(2-chlorophenyl)-N-phenylacetimidamide 

Relevant academic research and scientific papers

Access to pyrrolo[2,1-: A] isoindolediones from oxime acetates and ninhydrin via Cu(i)-mediated domino annulations

A copper-mediated domino condensation reaction of readily accessible oxime acetates with ninhydrin is reported to afford pyrrolo[2,1-a]isoindolediones via new C-C & C-N bond formations. A wide range of oxime acetates were shown to generally participate in the reaction to produce the condensed products in excellent yields. The necessary control experiments were performed and the mechanism is proposed to involve sequentially the formation of iminium radical via Cu-mediated N-O bond cleavage of oxime acetates, addition of the radical to ninhydrin and rearrangement via ring expansion.

CuCl2-catalyzed N[sbnd]O bond cleavage of oxime esters: Approach to imidazoheterocycles and furo[3,2-c]chromenyl fused imidazoles

An articulate approach to a diverse set of imidazoheterocycles in good to high yields via a copper-catalyzed aza-annulation of several oxime esters with a group of 2-amino-azaarenes was developed. The above cyclization reaction probably proceeds via a single electron transfer process which embodies a new technique for creating two new C[sbnd]N bonds for imidazole ring synthesis. Gratifyingly, the implementation of this chemistry could be further stretched to the synthesis of a novel class of fused imidazoles bearing a furo[3,2-c]chromene moiety via a sequential C[sbnd]N bond formation, followed by C(sp2)-H functionalization/5-endo-dig-oxacyclization (C[sbnd]C and C[sbnd]O bonds) of in situ produced fused imidazoles with cyclic enynones in the presence of copper(II) as a π-electrophilic Lewis acid catalyst.

Copper(0)/PPh3-Mediated Bisheteroannulations of o-Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls

A copper(0)/PPh3-mediated cascade bisheteroannulation reaction of o-nitroalkynes with methylketoximes has been developed that provides viable access to a diverse range of pyrazo-fused pseudoindoxyl compounds. Synthetically useful functional groups including sensitive C-I bonds are compatible with this system. Mechanistic studies suggest a reaction cascade involving sequential PPh3-mediated deoxygenative cycloisomerization and copper-catalyzed [3 + 2] pyrazo-annulation.

Direct access to bis-S-heterocycles via copper-catalyzed three component tandem cyclization using S8 as a sulfur source

A novel strategy for constructing sulfur containing bis-S-heterocyclic compounds from oxime esters/vinyl azide, phenylacetylene/aldehydes and elemental sulfur (S8) has been developed. These transformations show good functional group tolerance. Various bis-S-heterocyclic products were efficiently synthesized from easily prepared or widely commercially available starting materials. In this protocol, S8 successfully served as a two-sulfur atom donor for thiophene and thiazole rings, respectively.

Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions

A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.

Catalyst free synthesis of mono- and disubstituted pyrimidines from O-acyl oximes

Transition-metal or iodine catalyzed transformations of O-acyl oximes to various N-heterocycles are well established. Herein, we report a catalyst free, oxime carboxylate based, three-component condensation method to access mono- and disubstituted pyrimidines. A broad range of substituted pyrimidines were prepared in moderate to excellent yields. Control experiments reveal that in situ generated formamidine is the key intermediate.

Iron-Catalyzed Synthesis of 2H-Imidazoles from Oxime Acetates and Vinyl Azides under Redox-Neutral Conditions

A novel and versatile method for the synthesis of 2H-imidazoles via iron-catalyzed [3 + 2] annulation from readily available oxime acetates with vinyl azides has been developed. This denitrogenative process involved N-O/N-N bond cleavages and two C-N bond formations to furnish 2,4-substituted 2H-imidazoles. This protocol was performed under mild reaction conditions and needed no additives or ligands. Furthermore, this is a green reaction involving oxime acetate as internal oxidant, acetic acid, and nitrogen as byproducts.

Synthesis of symmetrical pyridines by iron-catalyzed cyclization of ketoxime acetates and aldehydes

A novel and facile iron-catalyzed cyclization of ketoxime acetates and aldehydes for the green synthesis of substituted pyridines has been developed. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce 2,4,6-triarylsubstituted symmetrical pyridines in high yields in the absence of any additive. A gram-scale reaction sequence was performed to demonstrate the scaled-up applicability of this synthetic method.

Iron-Catalyzed Cyclization of Ketoxime Carboxylates and Tertiary Anilines for the Synthesis of Pyridines

A novel and efficient iron-catalyzed cyclization of ketoxime carboxylates and N,N-dialkylanilines for the modular synthesis of diverse pyridines was developed. The reaction was initiated by Fe-catalyzed N-O bond cleavage of ketoxime carboxylates in the presence of tertiary anilines. The methylene carbon on N,N-dialkylanilines functioned as a source of one-carbon synthon in the reaction. The reaction used readily available starting materials, tolerated various functional groups, and afforded 2,4-disubstituted and 2,4,6-trisubstituted pyridines in good to high yields under mild conditions.