1629159-50-7

Upstream product

• 101089-41-2 (Z)-2-phenyl-1-(p-tolyl)ethan-1-one oxime 
• 124-63-0 methanesulfonyl chloride 
• 2430-99-1 1-phenyl-2-p-tolylethanone 
• 108-88-3 toluene 
• 5720-05-8 4-methylphenylboronic acid 
• 140-29-4 phenylacetonitrile 
• 101089-41-2 C₁₅H₁₅NO 
• 2001-28-7 2-phenyl-1-p-tolyl-ethanone 

Downstream Products

• 138073-16-2 dimethyl 2-phenyl-5-(p-tolyl)-1H-pyrrole-3,4-dicarboxylate 

Relevant academic research and scientific papers

Visible-Light-Promoted [3 + 2] Cycloaddition of 2H-Azirines with Quinones: Access to Substituted Benzo[f]isoindole-4,9-diones

A visible-light-promoteded [3 + 2] cycloaddition reaction of 2H-azirines with quinones has been developed under mild reaction conditions. The reaction provides a general and efficient strategy for the synthesis of the benzo[f]isoindole-4,9-diones scaffold

Zinc-Enabled Annulation of Trifluorodiazoethane with 2 H-Azirines to Construct Trifluoromethyl Pyrazolines, Pyrazoles, and Pyridazines

A diethylzinc-promoted unconventional annulation reaction of 2,2,2-trifluorodiazoethane with 2H-azirines is described. This transformation involves two [3 + 2] cycloaddition steps and one dinitrogen extrusion process in one pot, thus giving a broad array

Copper-Catalyzed Three-Component Carboboronation of Allenes Using Highly Strained Cyclic Ketimines as Electrophiles

A diastereoselective copper and NHC-ligand-catalyzed three-component difunctionalization of allenes with bis(pinacolato)diboron and 2H-azirines to afford borylated allylaziridines is described. The reaction exhibits complete diastereoselectivity and good yields, and the further chlorination of the corresponding borylated products was also performed. It is believed that the high ring-strain force of 2H-azirines facilitates the reaction. More chemical transformations of borylated allylaziridines are also reported.

A copper-catalyzed insertion of sulfur dioxide: Via radical coupling

A copper-catalyzed three-component reaction of O-acyl oximes, DABCO·(SO2)2, and 2H-azirines under mild conditions has been achieved. This protocol provides an efficient route for the construction of various tetrasubstituted β-sulfonyl N-unprotected enamines in moderate to good yields with excellent stereoselectivity and regioselectivity. Notably, this method represents a rare example of 2H-azirines as useful synthons for β-functionalized N-unprotected enamines. Preliminary mechanistic studies indicate that the reaction proceeds through coupling of a sulfonyl radical and α-carbon radical via copper-catalyzed ring-opening C-C bond cleavage of O-acyl oxime and C-N bond cleavage of 2H-azirine with the insertion of sulfur dioxide.

General Synthesis of Tri-Carbo-Substituted N2-Aryl-1,2,3-triazoles via Cu-Catalyzed Annulation of Azirines with Aryldiazonium Salts

The general synthesis of fully substituted N2-aryl-1,2,3-triazoles is hitherto challenging compared with that of the N1-aryl counterparts. Herein, we describe a Cu-catalyzed annulation reaction of azirines and aryldiazonium salts. This regiospecific metho

-Cycloaddition of 2 H-Azirines with Nitrosoarenes: Visible-Light-Promoted Synthesis of 2,5-Dihydro-1,2,4-oxadiazoles

A formal [3 + 2]-cycloaddition reaction of 2H-azirines with nitrosoarenes has been achieved under irradiation by visible light with the assistance of organic dye photoredox catalyst. This method utilizes nitrosoarenes as efficient radical acceptors and pr

Rhodium-catalysed synthesis of fused pyrimidine derivatives employing N-sulfonyl-1,2,3-triazoles as a 1-aza-[4C] synthon

A new synthetic application of N-sulfonyl-1,2,3-triazoles acting as a 1-aza-[4C] synthon via the 1,2-shift reaction of an α-imine rhodium carbene was developed for the synthesis of fused pyrimidine derivatives. The high reactivity of the strained three-me

Synthesis method of azacyclopropene compound

The invention discloses a synthesis method of an azacyclopropene compound represented as the formula (II). In the presence of alkali, the compound is prepared through an intramolecularly nucleophiliccyclization reaction to an oxime ester derivative represented in the formula (I); the R1 is selected from C1-C3 alkyl groups, phenyl group, substituted phenyl groups and naphthyl groups, wherein substituent groups in the substituted phenyl groups are selected from halogens, C1-C6 alkyl groups, C1-C6 alkoxyl groups, and cyclohexyl group; the R2 is selected from hydrogen and phenyl group; the R3 isselected from hydrogen, C1-C6 alkyl groups, and halogens. The method has gentle reaction conditions, low production cost, wide application range and high yield, and may be a simple new approach for synthesis of azacyclopropene compounds having medicinal activities.

Modular 2,3-diaryl-2: H -azirine synthesis from ketoxime acetates via Cs2CO3-mediated cyclization

A modular 2H-azirine synthesis from ketoxime acetates via Cs2CO3-mediated cyclization has been developed. The reaction utilizes easily available starting materials and provides a general synthetic route to 2,3-diaryl-2H-azirines in good to excellent yields under mild conditions, which is complementary to the conventional approaches for the synthesis of 2H-azirines. A gram-scale reaction was performed to demonstrate the scale-up applicability of this synthetic method. Importantly, 2H-azirines can be efficiently converted to various azaheterocycles.