20147-41-5

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 22755-09-5 N-phenyl hydroxylamine hydrochloride 
• 98-95-3 nitrobenzene 
• 586-96-9 Nitrosobenzene 
• 100-65-2 N-Phenylhydroxylamine 

Downstream Products

• 20147-53-9 2-phenyl-3-pyridin-3-yl-(3ar,6ac)-hexahydro-furo[3,2-d]isoxazole 
• 20147-46-0 3-(5-ethoxy-2-phenyl-isoxazolidin-3-yl)-pyridine 
• 82299-13-6 (E)-N-((pyridine-3-yl)methylene)benzenamine 

Relevant academic research and scientific papers

Investigations on regio- and stereoselectivities in cycloadditions involving α- (3-pyridyl)-N-phenylnitrone: Development of an efficient route to novel nicotine analogs

Thermal reactions of hitherto α-(3-pyridyl)-N-phenylnitrone (1) with mono-substituted electron-rich and electron-neutral dipolarophiles are regio-, and stereo-selective (exo-selective), controlled by LUMO-dipole - HOMO-dipolarophile interaction, and furnish syn-5-substituted-3-(3-pyridyl)- isoxazolidines (5) in high yields. With electron deficient dipolarophiles such as acrylonitrile there is observed a loss of regioselectivity as well as stereoselectivity and the regioselectivity is reversed in reactions with methyl vinyl ketone and methyl acrylate, due to intervention of HOMO-dipole - LUMO-dipolarophile interaction, affording 4-substituted-3-(3-pyridyl)- isoxazolidines (7) as major products. Reactions of nitrone (1) with disubstituted dipolarophiles such as methyl methacrylate and ethyl coronate furnish methyl syn-5-methy-3-pyridyl-1-phenyl-isoxazolidine-5-carboxylate (8) and ethyl anti-5-methy-3-pyridyl-1-phenyl-isoxazolidine-4-carboxylate (10), respectively, in high yields. Reaction with N-Phenylmaleimide affords novel isoxazolidino-pyrrolidinediones bearing a 3-pyridyl moiety (11, 12). A mechanistic rationalization of the obtained results in terms of electronic, steric and secondary interactions is proffered.

Highly Electron-Deficient Pyridinium-Nitrones for Rapid and Tunable Inverse-Electron-Demand Strain-Promoted Alkyne-Nitrone Cycloaddition

Highly accelerated inverse-electron-demand strain-promoted alkyne-nitrone cycloaddition (IED SPANC) between a stable cyclooctyne (bicyclo[6.1.0]nonyne (BCN)) and nitrones delocalized into a Cα-pyridinium functionality is reported, with the most

Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide

A new Kinugasa reaction protocol has been elaborated for the one-pot synthesis of 4-substituted β-lactams utilizing calcium carbide and nitrone derivatives. Calcium carbide is thereby activated by TBAF·3H2O in the presence of CuCl/NMI. The ease of synthesis and use of inexpensive chemicals provides rapid access of practical quantities of β-lactams exclusively substituted at position 4.

Metal-free approach for the ?-proline mediated synthesis of nitrones from nitrosobenzene

An efficient, and metal-free approach for the ?-proline mediated synthesis of nitrones from nitrosobenzene and benzaldehydes has been established. The reaction undergoes very efficiently at room temperature in methanol as a solvent. The reaction is assumed to involve that the initial formation of azomethine ylide and [2 + 3] cycloaddition of nitrosobenzene, followed by the subsequent retro [2 + 3] cycloaddition could offer the desired nitrone.

Formation and reductive ring opening reactions of indolyl-isoxazolidines: Access to novel natural product analogs and precursors

Regio- and stereoselective 1,3-dipolar cycloadditions of C-(3-indolyl)-N-phenylnitrone (2) with variedly substituted dipolarophiles were carried out to obtain syn- C4 and C5 substituted indolyl-isoxazolidines 6a-c and 7a-f, respectively. Reduction of obtained isoxazolidines, by employing various reducing agents, causes cleavage of the N-O bond, which is accompanied by concomitant cleavage of C-N bond leading to the formation of a library of novel indole based natural product analogs and precursors.

Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4 + 2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines

An iron-catalyzed intermolecular [4 + 2] cyclization of arylnitrones with geminal-substituted vinyl acetates was developed for the synthesis of 2,4-disubstituted quinolines in moderate to good yields with good functional group compatibilities. Preliminary mechanistic studies suggest a plausible iron-catalyzed C-H activation process under external-oxidant-free conditions.

Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines

Microwave irradiation allows increasing the speed of several reactions and also offers the possibility of eliminating poisoning organic solvents. In this work we report the microwave-assisted neat synthesis of α-phenyl-tert-butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans-crotonate.