68702-72-7

Upstream product

• 100-65-2 N-Phenylhydroxylamine 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 20972-43-4 trans-azoxybenzene 
• 68702-71-6 (3S,4S,5R)-3-Isopropyl-5-methyl-2-phenyl-isoxazolidine-4-carboxylic acid methyl ester 
• 344873-43-4 4-Isopropyl-1,3-diphenyl-azetidin-2-one 

Relevant academic research and scientific papers

Catalytic Selective Oxidative Coupling of Secondary N-Alkylanilines: An Approach to Azoxyarene

Azoxyarenes are among important scaffolds in organic molecules. Direct oxidative coupling of primary anilines provides a concise fashion to construct them. However, whether these scaffolds can be prepared from secondary N-alkylanilines is not well explored. Here, we present a catalytic selective oxidative coupling of secondary N-alkylaniline to afford azoxyarene with tungsten catalyst under mild conditions. In addition, azoxy can be viewed as a bioisostere of alkene and amide. Several "azoxyarene analogues" of the corresponding bioactive alkenes and amides showed comparable promising anticancer activities.

Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives

Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza-1-buten-3-ynes in good yields.In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products.The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used.Asymmetric induction is also observed in the reaction of phenylacetylene with α,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.

THE SIMPLEST PHENYLNITRONES AND THEIR CONVERSION INTO ISOXAZOLIDINE DERIVATIVES

Reaction of N-phenylhydroxylamine with the simplest alkanals leads initially to the formation of N-phenylnitrones, dimerization of which gives 5-substituted isoxazolidine.Taking the reactions of N-phenylnitrones, benzaldehyde, and acetone as an example, t

The Influence of Steric and Electronic Effects on the Stability of Aldonitrones and on their Conversion into Isoxazolidines

The nitrones 3Aa-Ai were isolated from the reaction of tert-butylhydroxylamine (1A) with aldehydes 2a-i. 1B-D react in an analogous manner. 3Aa-Ac convert slowly into the isoxazolidines 5Aa-Ac, whereas 3Ad-Ai do not.Phenylhydroxylamine (1F) reacts with 2a-d to yield 5Fa-Fd, likewise compounds 5Ea, Ed and the rearranged product 5Ub are formed from 1E.Reaction of 1F and 2f-h, however, yields the nitrones 3Ff-Fh. 3Ff exists in an equilibrium with a dimer of structure 6. - Compounds 5Aa-Ac were found to undergo cycloreversion to give the nitrones 3 in solution, whereas 5Fa-Fd as well as 5Ea, Ub, and Ed did not.There is a steady decrease in the tendency for cycloreversion in the order 5Ab > 5Bb > 5Cb, however, the degree of cycloreversion is also solvent-dependent.Acyclic compounds 7 were found to be intermediates in the conversion of 5Aa and Bb into the corresponding nitrones.Compound 9, formed from 1A and acrolein (8), does not decompose to yield its components 3Aa and 11.The influence of electronic and steric effects on the relative stability of the nitrones 3 and isoxazolidines 5 is discussed.