16205-14-4

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 2157-50-8 propiophenone oxime 
• 873-66-5 1-propenylbenzene 
• 1532565-46-0 (1-azido-2-iodopropyl)benzene 
• 637-50-3 1-phenylpropene 

Downstream Products

• 54600-85-0 2,5-dimethyl-3,6-diphenylpyrazine 
• 86756-07-2 2,5-Dimethyl-6-phenyl-4H-[1,4]oxazin-3-one 
• 86756-08-3 (1R,3R,4S,5S,6R)-1,3,6-Trimethyl-4,5-diphenyl-9-oxa-2,7-diaza-tricyclo[3.3.1.0^2,4]nonan-8-one 
• 89414-88-0 (3R,4S)-4-Methyl-2,5-dioxo-4-phenyl-pyrrolidine-3-carboxylic acid ethyl ester 
• 131202-52-3 Triphenyl-3,4,5 (amino-1' ethyl)-5 4H,5H-isoxazole 
• 131202-53-4 t-Butyl-3 phenyl-5 (amino-1' ethyl)-5 4H,5H-isoxazole 
• 82193-54-2 2-Methyl-4-(1-methyl-allyl)-3-phenyl-1H-pyrrole 
• 86756-04-9 3-[2-Amino-1-phenyl-prop-(E)-ylideneamino]-propionic acid ethyl ester 
• 77329-90-9 2,6-Dimethyl-3,5-diphenyl-1,4-diaza-bicyclo[3.2.0]hept-3-en-7-one 
• 41964-86-7 6-Methyl-2-oxo-5-phenyl-1,2-dihydropyrazine 
• 86756-02-7 3,6-Dimethyl-5-phenyl-1H-pyrazin-2-one 
• 92971-89-6 2-Methyl-3-phenyl-4-vinyl-1-aza-bicyclo[1.1.0]butane 

Relevant academic research and scientific papers

Aziridation of Vinylsilanes and Vinylstannanes: A New Synthesis of Azirines

Aziridination of vinylsilanes and vinylstannanes with N-acetoxyaminoquinazolone (8) gave aziridines (1)-(7): caesium fluoride in dimethylformamide brought about elimination of trimethylsilyl and quinazolone groups from (1) and (2) to give the correspondin

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

A Domino Approach for the Synthesis of 4-Carboxamide Oxazolines from Azirines

A regio- and diastereoselective ring-expansion reaction of N-acylaziridines is described for the synthesis of 4-carboxamide oxazolines using InCl3. A domino Ugi-Joullié/ring-expansion reaction of arylphenylazirines, isocyanides, and carboxylic

Self-Catalyzed Rapid Synthesis of N-Acylated/ N-Formylated α-Aminoketones and N-Hydroxymethylated Formamides from 3-Aryl-2 H-Azirines and 2-Me/Ph-3-Aryl-2 H-Azirines

A rapid and effective method has been established for the synthesis of N-acylated α-aminoketone derivatives by the reaction of 3-aryl-2H-azirines and highly substituted 2-Me/Ph-3-aryl-2H-azirines with various carboxylic acids under ambient air within 10 min at room temperature. N-Trifluoroacetylated α-aminoketones with different substituents have been reported in the presence of trifluoroacetic acid. This protocol is equally effective to synthesize N-formylated α-aminoketone and N-hydroxymethylated formamide derivatives.

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

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

RhII-catalyzed [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles

RhII-catalyzed intermolecular [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza-[3 C] synthons, which have been reported previously in cyclopropanations and [3 + n] cycloadditions. Moreover, this methodology has also been successfully applied in the total synthesis of URB447 as well as the formal synthesis of Atorvastatin (Lipitor).

Gold-Catalyzed Intermolecular Nitrene Transfer from 2H-Azirines to Ynamides: A Direct Approach to Polysubstituted Pyrroles

(Chemical Equation Presented). An effective gold-catalyzed intermolecular nitrene transfer by the reaction of 2H-azirines and ynamides is reported, which provides highly substituted pyrroles in a straightforward manner. This transformation proceeds under mild conditions and gives the polysubstituted pyrroles in good-to-excellent yields. Preliminary results indicate that a nongold carbenoid pathway is preferred for current pyrrole synthesis.

Synthesis of unsymmetrical pyrazines based on ?±-diazo oxime ethers

Synthesis of unsymmetrically substituted pyrazines has been a challenge. The reactivity of ?±-imino carbenoids derived from ?±-diazo oxime ethers has been exploited for pyrazine synthesis, in which the reaction of ?±-diazo oxime ethers with 2H-azirines provides highly substituted pyrazines in good to excellent yields.

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.