abstract

• 2-chloro-3-(R-anilino)-1,4-naphthoquinones react with sodium azide upon refluxing in DMF. The thermochemistry of 2-azido-3-(R-anilino)-1,4-naphthoquinone is strongly modified by the substituent on aniline. Having an strong electron-donor like O-R results in the generation of a phenazine while having an electron-withdrawing substituent results in the formation of 2-amino-3-(R-anilino)-1,4-naphthoquinone. The products obtained are explained in terms of singlet and/or triplet nitrene chemistry. © 2020 Elsevier Ltd

authors

• Cárdenas-Chaparro A.
• Leyva Ramos Elisa
• Loredo Carrillo Silvia Elena
• Martínez-Richa A.
• Platz M.S.

publication date

• 2020-01-01

funding provided via

• Consejo Nacional de Ciencia y Tecnologí­a, CONACYT: 155678  Grant

published in

• Tetrahedron Letters  Journal

keywords

• 2-azido-3-(R-anilino)-1; 4-naphthoquinones; Hydrogen abstraction; Insertion; Nitrene; Thermolysis 1,4 naphthoquinone derivative; 2 azido 3 (anilino) 1,4 naphthoquinone; unclassified drug; Article; carbon nuclear magnetic resonance; chemical structure; lysis; mass spectrometry; proton nuclear magnetic resonance; structure analysis; thermolysis; ultraviolet visible spectroscopy

Digital Object Identifier (DOI)

• 10.1016/j.tetlet.2020.151731

start page

end page

volume

• 61

issue

• 14