78569-38-7

Upstream product

• 66-77-3 1-naphthaldehyde 
• 62-53-3 aniline 
• 4780-79-4 1-naphthalene methanol 

Downstream Products

• 4044-57-9 1-phenylethynyl-naphthalene 
• 98977-82-3 (E)-N-phenyl-N-(3-phenyl-2-propenyl)-1-naphthalenemethanamine 
• 53693-50-8 (naphthalen-1-ylphenylmethyl)phenylamine 
• 7182-94-7 N-(Naphthalen-1-ylmethyl)benzenamine 
• 135569-49-2 cis-1-phenyl-3-(methylphenylamino)-4-(α-naphthyl)-2-azetidinone 

Relevant academic research and scientific papers

A Highly Selective Manganese-Catalyzed Synthesis of Imines under Phosphine-Free Conditions

An efficient and highly selective phosphine-free NN-manganese(I) complex catalyst system was developed for the acceptorless dehydrogenative coupling of alcohols with amines to form imines. The coupling reactions underwent at 3 mol % catalyst loading, and a large range of alcohols and amines with diverse functional groups was applied, including challenging diol and diamine. The target imine products were obtained in good to excellent yields. The present work provides an alternative method to construct highly active nonprecious metal complex catalysts based on phosphine-free ligands.

Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids

(Chemical Equation Presented) Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium-(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.

Electronic and steric control in regioselective addition reactions of organolithium reagents with enaldimines

A reaction mode of imines derived from naphthalene-1-carbaldehyde and acyclic α,β-unsaturated aldehydes with organolitium reagents was dependent on the characteristic nature of a substituent on the imine nitrogen atom. An imine having an electron-withdrawing aryl group on the nirtogen atom behaves as a 1,2-directing imine toward organolithium reagents. In contrast, an imine bearing an alkyl or a bulky aryl group favors 1,4-addition of organolithium reagents. Electronic and steric tuning of a substituent on the imine nitrogen atom for a reaction mode was rationalized on the basis of molecular orbital calculations.

Cycloaddition of (N-Alkyl-N-phenylamino)ketene with Imines

(N-Alkyl-N-phenylamino)ketenes were prepared in the presence of various imines, and a cycloaddition reaction occurred to yield 3-(N-alkyl-N-phenylamino)-2-azetidinones.The size and electronic nature of the imine substituents were varied in order to probe those factors that influence the stereochemistry of the cycloaddition.The stereochemistry of the 2-azetidinone was determined by the substitution pattern of the imines.In general, the stereochemistry of the 2-azetidinone products are significantly influenced by the bulk of the N substituent on the imine.These results are discussed in terms of a two-step zwitterionic intermediate.

Synthesis and Structure-Activity Relationships of Naftifine-Related Allylamine Antimycotics

Naftifine (1) is the first representative of the new antifungal allylamine derivatives.Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals.A tertiary allylamine function seems to be a prerequisite for activity against fungi.By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations.Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.