22596-45-8

Upstream product

• 705-60-2 1-phenyl-2-nitroprop-1-ene 
• 705-60-2 (2-nitroprop-1-enyl)benzene 
• 22596-45-8 trans-2-methyl-2-nitro-3-phenyloxirane 
• 62-53-3 aniline 
• 134-32-7 1-amino-naphthalene 
• 91-59-8 naphthalen-2-ylamine 
• 104-94-9 4-methoxy-aniline 
• 91-60-1 2-Naphthalenethiol 
• 95-54-5 1,2-diamino-benzene 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 
• 100-52-7 benzaldehyde 

Downstream Products

• 579-07-7 1-Phenylpropane-1,2-dione 
• 4773-35-7 1-chloro-1-phenylpropan-2-one 
• 70071-08-8 2,6,7-trimethyl-3-phenylquinoxaline 
• 826-83-5 4(5)-phenyl-5(4)-methylimidazole 
• 13739-49-6 2,5⁽⁴⁾-dimethyl-4⁽⁵⁾-phenylimidazole 
• 2654-31-1 5⁽⁴⁾-methyl-2,4⁽⁵⁾-diphenylimidazole 
• 31483-79-1 2-(4-Methoxy-phenyl)-5-methyl-4-phenyl-1H-imidazole 
• 34658-68-9 3-methyl-2-phenyl-1H-imidazo[1,2-a]pyridine 
• 28241-62-5 2-Amino-4-methyl-5-phenyl-thiazol 

Relevant academic research and scientific papers

Diindenopyrazines: Electron-Deficient Arenes

The syntheses, properties and application of the air-stable electron acceptors, diindenopyrazines 4 a–g are reported demonstrating the introduction of functional aryl groups in the 6- and 12-positions. The targets are accessible on the hundred milligram to gram scale. The structure of the aryl groups in 4 a–g modulates their solubility, redox potentials and optical properties. The introduction of electron-poor aryl groups to the electron-poor diindenopyrazine backbone reduces the electron affinity to ?4 eV, making the compounds attractive as n-semiconductors. A simple organic field-effect transistor of 4 e –without optimization– shows electron transport with a mobility of up to 0.037 cm2 V?1 s?1.

Catalyst-Free Synthesis of Benzofuran Derivatives from Cascade Reactions between Nitroepoxides and Salicylaldehydes

Different benzofuran derivatives are synthesized via a catalyst-free reaction between nitroepoxides and salicylaldehydes. In the employed methodology, K2CO3 and DMF have been used at 110 °C, and the reactions were completed after 12 h in 33-84% yields. Th

Regioselective Opening of Nitroepoxides with Unsymmetrical Diamines

Nitroepoxides are easily transformed into benzodiazepines, tetrahydrobenzodiazepines, imidazopyridines, and N-alkyl tetrahydroquinoxalines by treatment with 2-aminobenzylamines, 2-aminopyridines, and N-alkyl 1,2-diaminobenzenes, respectively. Regioselectivity is controlled through attack of the most nucleophilic nitrogen of the unsymmetrical diamine to the β position of the epoxide. These reactions represent an efficient way to prepare privileged bioactive structures.

Catalytic enantioselective epoxidation of nitroalkenes

Nitroepoxides are potentially exploitable as synthons with vicinal electrophilic centers. Nevertheless, although advances have been made in the field, enantioselective epoxidation of nitroalkenes is still a challenging process. Herein we show a convenient procedure for the preparation of optically active nitroepoxides in high enantiomeric excess and high chemical yield. The kinetic data of the best catalyst have been examined using computational methods based on DFT calculations. Interestingly, the results demonstrate that the enantioselectivity of the epoxidation of nitroalkenes by this kind of catalyst is not only kinetically but also thermodynamically controlled.

Preparation of Morpholines and Benzoxazines Starting from Nitroepoxides

Nitroepoxides are easily transformed into 2,3-disubstituted morpholines and 2,3-disubstituted benzoxazines in a two-step sequence by treatment with N-methylethanolamine and N-methyl-2-hydroxyaniline, respectively, in a highly stereoselective fashion.

Catalytic enantioselective synthesis of α-nitroepoxides via aminolytic kinetic resolution

The first enantioselective synthesis of β-aryl-substituted α-nitroepoxides, exploiting an organocatalyzed aminolytic kinetic resolution (AKR), has been developed. Ring-opening reaction of racemic α-nitroepoxides with aniline in the presence of a readily available Cinchona alkaloid-derived thiourea affords unreacted epoxides in up to 95% ee.

Nitroepoxides as versatile precursors to 1,4-diamino heterocycles

Nitroepoxides are easily transformed into 1,4-diamino heterocycles such as quinoxalines and pyrazines by treatment with 1,2-benzenediamines and ammonia, respectively. Additionally, related saturated heterocycles, such as piperazines and tetrahydroquinoxalines, can be accessed by treatment with 1,2-diamines and a reducing agent. These transformations are efficient, provide access privileged, bioactive structures, and produce minimal waste.

α-nitro epoxides in organic synthesis: Development of a one-pot organocatalytic strategy for the synthesis of quinoxalines

A new strategy for the synthesis of biologically active quinoxalines by using versatile α-nitro epoxides as starting compounds has been developed. In addition, the in situ organocatalytic epoxidation of electron-poor nitro olefins followed by condensation with 1,2-phenylenediamines to provide quinoxalines in one pot has been demonstrated. The reaction of easily accessible nitro olefins with the tBuOOH/1,8-diazabicycloundec-7-ene (TBHP/DBU) organocatalytic system gives rise to the corresponding α-nitro epoxides, which are suitable for subsequent reaction with 1,2-phenylenediamines under mild conditions to give quinoxaline heterocycles in up to 82 % yield. Copyright

α-Nitro Epoxides in Organic Synthesis: Development of a One-Pot Organocatalytic Strategy for the Synthesis of Quinoxalines

A new strategy for the synthesis of biologically active quinoxalines by using versatile α-nitro epoxides as starting compounds has been developed. In addition, the in situ organocatalytic epoxidation of electron-poor nitro olefins followed by condensation with 1,2-phenylenediamines to provide quinoxalines in one pot has been demonstrated.

Dynamic kinetic asymmetric ring-opening/reductive amination sequence of racemic nitroepoxides with chiral amines: Enantioselective synthesis of chiral vicinal diamines

We report a highly diastereoselective synthesis of vicinal diamines by the treatment of nitroepoxides with primary amines and then a reducing agent. When using a chiral primary amine, racemic nitroepoxides are transformed into chiral diamines as a single enantiomers (>95:5 er) through a dynamic kinetic asymmetric transformation (DYKAT). The overall process is a one-pot procedure combining the exposure of nitroepoxides to chiral amines to afford diastereomeric mixtures of aminoimines and subsequent stereoselective imine reduction.