76928-56-8

Upstream product

• 20544-84-7 (Z)-(2-azidoprop-1-en-1-yl)benzene 
• 873-66-5 1-propenylbenzene 
• 13213-36-0 1-phenylpropan-2-one oxime 
• 34431-91-9 (E,Z)-1-Azido-1-phenyl-1-propen 
• 103-79-7 1-phenyl-acetone 
• 114971-31-2 1-phenylpropan-2-one O-acetyl oxime 

Downstream Products

• 100-52-7 benzaldehyde 
• 23022-83-5 1-bromo-1-phenyl-2-propanone 
• 103-79-7 1-phenyl-acetone 
• 13901-69-4 dimethyl 2-methyl-5-phenyl-1H-pyrrole-3,4-dicarboxylate 
• 92314-62-0 C₉H₉N 
• 1431934-96-1 ethyl 3,6-dimethyl-2-phenyl-2H-1,4-oxazine-5-carboxylate 

Relevant academic research and scientific papers

Comparison of the photochemistry of 3-methyl-2-phenyl-2h-azirine and 2-methyl-3-phenyl-2h-azirine

Photolysis of 3-methyl-2-phenyl-2H-azirine (1a) in argon-saturated acetonitrile does not yield any new products, whereas photolysis in oxygen-saturated acetonitrile yields benzaldehyde (2) by interception of vinylnitrene 5 with oxygen. Similarly, photolysis of 1a in the presence of bromoform allows the trapping of vinylnitrene 5, leading to the formation of 1-bromo-1-phenylpropan-2-one (4). Laser flash photolysis of 1a in argon-saturated acetonitrile (? = 308 nm) results in a transient absorption with ?max at 440 nm due to the formation of triplet vinylnitrene 5. Likewise, irradiation of 1a in cryogenic argon matrixes through a Pyrex filter results in the formation of ketene imine 11, presumably through vinylnitrene 5. In contrast, photolysis of 2- methyl-3-phenyl-2H-azirine (1b) in acetonitrile yields heterocycles 6 and 7. Laser flash photolysis of 1b in acetonitrile shows a transient absorption with a maximum at 320 nm due to the formation of ylide 8, which has a lifetime on the order of several milliseconds. Similarly, photolysis of 1b in cryogenic argon matrixes results in ylide 8. Density functional theory calculations were performed to support the proposed mechanism for the photoreactivity of 1a and 1b and to aid in the characterization of the intermediates formed upon irradiation.

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

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.

Rh(ii)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: Switchable reactivity of Rh-azavinylcarbene as [2C]- or aza-[3C]-synthon

The Rh(ii)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions. This journal is

Visible-light-induced formal [3+2] cycloaddition for pyrrole synthesis under metal-free conditions

A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful. Photo(chemistry) op: A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been established under the irradiation of visible light in the presence of an organic dye. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the formal synthesis of an inhibitor for HMG-CoA reductase.

Evidence for Vinyl Nitrene Intermediates in the Thermal Rearrangement of 2H-Azirines into Indoles

Thermal racemization of optically active 3-methyl-2-phenyl-2H-azirine was found to be 2039 times faster than its rearrangement into 2-methylindole, which furnished firm evidence for the presence of vinyl nitrenes as intermediates.