22950-23-8

Usage

Uses

Used in Pharmaceutical Industry:
N-(prop-2-en-1-yl)naphthalen-1-amine is used as a building block for the synthesis of various pharmaceuticals due to its unique structure and reactivity. Its presence in the molecular structure can contribute to the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, N-(prop-2-en-1-yl)naphthalen-1-amine serves as a key component in the synthesis of various agrochemicals, potentially enhancing the effectiveness of these compounds in agricultural applications.
Used in Dye Production:
N-(prop-2-en-1-yl)naphthalen-1-amine is also used in the production of dyes, where its chemical properties contribute to the creation of dyes with specific color characteristics and stability.
Used in Organic Synthesis:
In the field of organic synthesis, N-(prop-2-en-1-yl)naphthalen-1-amine is utilized as a versatile intermediate for the synthesis of a wide range of organic compounds, showcasing its potential in various chemical reactions and applications.

Upstream product

• 134-32-7 1-amino-naphthalene 
• 106-95-6 allyl bromide 
• 78977-64-7 N-allyl-N-trifluoroacetyl-1-naphthylamine 
• 107-05-1 3-chloroprop-1-ene 
• 591-87-7 Allyl acetate 
• 837-78-5 N-trifluoroacetyl-α-naphthylamine 
• 35466-83-2 allyl methyl carbonate 
• 107-18-6 allyl alcohol 
• 7575-57-7 allyl benzenesulfonate 

Downstream Products

• 607-60-3 N-propylnaphthalen-1-amine 
• 82238-92-4 N-(1-naphthyl)pyrrolidine 
• 78977-71-6 2-(2-propenyl)-1-naphthylamine 
• 134-32-7 1-amino-naphthalene 
• 1226515-69-0 N,2-diallyl-N-tosyl-1-naphthylamine 
• 1226515-82-7 1-tosyl-2,5-dihydro-1H-naphtho[1,2-b]azepine 
• 1316312-15-8 N-(2-buta-1,3-dienyl-naphthalen-1-yl)-4-methyl-benzenesulfonamide 
• 1599475-53-2 C₂₂H₂₁IN₂S 
• 1599475-52-1 C₂₁H₁₉IN₂OS 
• 1599475-51-0 C₂₀H₁₆FIN₂S 
• 1599475-50-9 C₂₀H₁₆ClIN₂S 
• 1599475-49-6 C₂₀H₁₇IN₂S 
• 863656-29-5 2-(2-propenyl)-1-(triphenylphosphoranylideneamino)naphthalene 
• 863656-31-9 13-phenyl-7,7a,8,14-tetrahydrodibenzo[b,h]acridine 

Relevant academic research and scientific papers

Direct palladium(0)-catalyzed amination of allylic alcohols with aminonaphthalenes

The direct activation of C-O bonds in allylic alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium reagents. The palladium-catalyzed amination of allylic alcohols using aminonaphthalenes gave N-all

Synthesis of novel [3,1]-benzothiazepine and [3,1]-benzoxazepine derivatives with antitumoral activity

A new method for the synthesis of [3,1]-benzothiazepines and [3,1]-benzoxazepines from the reaction of C-allylanilines and isothiocyanates or isocyanates without the need for the isolation of any intermediate is described. The compounds were obtained in good to moderate yields and some exhibited cytotoxic activity against tumor cell lines. This journal is the Partner Organisations 2014.

PEG-4000-promoted palladium-catalyzed N-allylation in water: Aminonaphthalene as an example

An environmentally friendly, efficient catalytic process using palladium associated with ligands in a PEG4000-water system leading to N-allylation was described in this study. PEG-4000 was found to improve the palladium-catalyzed allylic amination of allylic acetates with aminonaphthalenes and gave overall good to high yields of the corresponding N-allylic aminonaphthalenes. Copyright

Sequential combination of ruthenium-, base-, and gold-catalysis - A new approach to the synthesis of medicinally important heterocycles

A general approach to the high-yielding synthesis of medicinally important heterocycles was achieved through the sequential combination of ring-closing metathesis, base-induced ring opening (BIRO), hydroamination, and a Diels-Alder reaction of functionalized allyl-(2-allylphenyl)amines in the presence of a catalytic amount of Grubbs' second-generation catalyst, base (tBuOK), and [AuCl(PPh3)]/AgOTf. Herein, we also demonstrate the important electronic factors in the BIRO of N-substituted-benzo[b]azepines for the regioselective synthesis of functionalized (Z)-N-substituted-2-(buta-1,3-dienyl) phenylamines in very good yields with high purity; these are very good, useful compounds in medicinal chemistry. We also discovered the selective cascade synthesis of privileged hexahydrophenanthridines from (Z)-N-substituted-2-(buta- 1,3-dienyl)phenylamines by gold catalysis in moderate to good yields with >99 % diastereomeric excess. The possible reaction mechanism for the unusual hydroamination followed by [4+2] cycloaddition of functionalized (Z)-N-substituted-2-(buta-1,3-dienyl)phenylamines through gold catalysis is discussed in this work. A novel process for the synthesis of highly substituted, medicinally important heterocycles was achieved through the sequential combination of ring-closing methathesis, base-induced ring opening, hydroamination, and Diels-Alder reaction of functionalized allyl-(2-allylphenyl) amines in the presence of a catalytic amount of [Ru], base, and [Au] (see scheme). Copyright

Synthesis of azepine- and azocine-annulated heterocycles by aromatic aza-Claisen rearrangement and ring-closing metathesis

Syntheses of hitherto unreported azepine- and azocine-annulated heterocycles have been developed in excellent yields via a catalyzed aromatic aza-Claisen rearrangement followed by ring-closing metathesis using Grubbs first-generation catalyst. Georg Thiem

Platinum-catalyzed allylation of aminonaphthalenes with allylic acetates in water

The activation of C-O bonds in allylic acetates in water as a suspension medium has been accelerated by carrying out the reactions in the presence of platinum complexes associated with ligands. The platinum-catalyzed allylation of aminonaphthalenes using allylic acetates gave the corresponding N-allylic aminonaphthalenes in good yields.

An improved method of synthesis of precursors for amino-Claisen rearrangement

N-Allylarylamines are useful precursors in amino-Claisen rearrangements affording 2-allylarylamines in one step. An improved method for the synthesis of a series of N-allylarylamines (2a-h) has been described.

Platinum-catalyzed allylation of aminonaphthalenes with allylic acetates

The activation of C-O bonds in allylic acetates has been accelerated by carrying out the reactions in the presence of platinum complexes associated with ligands. Platinum-catalyzed allylation of aminonaphthalenes with allylic acetates leads to N-allylic aminonaphthalenes in good yields.

Thermal cyclization of N-[2-(2-propenyl)-1-naphthyl] ketenimines: Intramolecular Diels-Alder reaction versus [1,5] hydrogen migration. Synthesis of dibenz[b,h]acridines and benzo[h]quinolines

The thermal treatment of N-(2-propenyl)-1-naphthylamines provided the expected aza-Claisen rearranged products, 2-(2-propenyl)-1-naphthylamines and benz[g]indoles, these last derived from an intramolecular hydroamination reaction on those primary products. The 2-(2-propenyl)-1-naphthylamines were converted into their triphenylphosphazene derivatives, which by aza-Wittig reaction with disubstituted ketenes yielded N-[2-(2-propenyl)-1-naphthyl] ketenimines. The heating of these ketenimines in boiling toluene induced their cyclization either via an intramolecular Diels-Alder reaction, to afford dibenz[b,h]acridines, or via [1,5] hydrogen migration from the sp3 carbon atom of the propenyl substituent to the central carbon atom of the ketenimine fragment, followed by a 6π electrocyclic ring closure, to give benzo[h]quinolines.

Thermal Rearrangement of N-(Substituted allyl)-1-naphthylamines

The title reaction was examined and the results were compared with those of the thermal reaction of the corresponding N-tosyl derivatives.