Variations in product in reactions of naphthoquinone with primary amines

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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) (I) 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.

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Singh, M. W., Karmakar, A., Barooah, N., & Baruah, J. B. (2007). Variations in product in reactions of naphthoquinone with primary amines. Beilstein Journal of Organic Chemistry, 3. https://doi.org/10.1186/1860-5397-3-10

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