Variations in product in reactions of naphthoquinone with primary amines

Abstract

Reaction of 1,2-naphthoquinone with primary amines gives a 2-amino-1,4-naphthoquinone derivative which is equivalent to 1,2 to 1,4 carbonyl transposition. For example the reaction of 1,2-naphthoquinone with 4-methoxyaniline gives 2-(4-methoxyanilino)-naphthoquinone-1,4-(4-methoxyanil) (1) and with n-butylamine gives 2-(butylamino)-naphthoquinone-1,4-butylimine (2) respectively. The compounds 1 and 2 are characterized by X-ray crystallography; they have hydrogen-bonded dimeric structures. Similar reaction of 1,4-naphthoquinone with 3-picolylamine and 4-picolylamine gives the corresponding 2-amino 1,4-naphthoquinones; two products are characterized by X-ray crystallography. The reaction of 1,4-naphthoquinone with 4-aminothiophenol and 1,4-naphthoquinone with 4-aminophenol are compared. The former leads to C-S and the latter to C-N bond formation. The reaction of 1,4-naphthoquinone with 4-aminothiophenol in an NMR tube is studied to explain that 2-(4-anilinothiolato) 1,4-naphthoquinone derivative to be the sole product in the reaction.

The detection of latent fingermarks on porous surfaces using amino acid sensitive reagents: A review

“…Naphthoquinones are a class of compounds that are well known for their bioactivity [116,117] and their ability to react with amino groups have been extensively reported [115,[118][119][120][121][122][123][124][125][126][127][128][129]. 1,2-naphthoquinone-4-sulfonate has been employed for the determination of amino acids through the formation of highly coloured compounds [130][131][132][133][134].…”

Quinone Tethered Silylethers: Protein Binding and Film Forming Abilities

“…The compounds 1-3 were prepared by reacting respective quinone with 3-mercaptopropyl-trimethoxysilane adopting procedure which was earlier followed for synthesis of similar mono-substituted C-S bonded quinones (23,24). The formation of the C-S bonded compounds in each case was confirmed by comparing the powder XRD, IR and other spectroscopic properties of the products with starting compounds.…”

“…We have observed that the quinones easily lead to the formation of C-S bond without addition of a reagent. Such C-S bond forming reactions not only maintain atom economy but also lead to desired products under ambient condition (23,24). Hybrid materials derived from alkoxysilane interact with proteins (25,26), modifies cell membranes (27), causes corrosion inhibition (28), used in analytical chemistry for metal detections (29,30) and are also used to make magnetic materials (31).…”

Crystal structure of (E)-2-(tert-butylamino)-4-(tert-butylimino)naphthalen-1(4H)-one

“…A search of the Cambridge Structural Database (Version 5.39, update February 2018; Groom et al, 2016) for the substructure 2-(alkylamino)-4-(alkylimino)naphthalen-1(4H)-one yielded three hits. Two of the structures, ESOFID (Schweinfurth et al, 2016) and UDAZEF (Singh et al, 2007) have aromatic amines (aniline or substituted aniline) as the amine moiety. Only one structure, UDAZIJ (Singh et al, 2007), has an aliphatic primary amine (n-butylamine) at positions 2 and 4.…”