On the Reaction of 2-Benzylamino-1,4-naphthoquinones with Nitrosylsulfuric Acid

• Published in: Russian journal of organic chemistry Vol. 55; no. 5; pp. 608 - 614
• Main Authors: Gornostaev, L. M., Nuretdinova, E. V., Lavrikova, T. I., Khalyavina, Yu. G., Fominykh, O. I., Gatilov, Yu. V.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.05.2019; Springer Nature; Springer Nature B.V
• Subjects: Acetic acid; Acids; Benzaldehyde; Benzamide; Chemistry; Chemistry and Materials Science; Chemistry, Organic; Imidazole; Organic Chemistry; Physical Sciences; Science & Technology; 2,3-diazido-1,4-naphthoquinone; naphtho-1,2-oxazole; 2-benzylamino-1,4-naphthoquinone; nitrosylsulfuric acid; oximes; hydroxyimidazole; 2-oxazole; 3-diazido-1; 2; 2-ALKYLAMINO-1,4-NAPHTHOQUINONES; 4-naphthoquinone; naphtho-1; DERIVATIVES; 2-benzylamino-1
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428019050051

The reaction of 2-benzylamino-1,4-naphthoquinone with nitrosylsulfuric acid in acetic acid results in preferential formation of 2,1- and 2,3-heterocyclization products: ( E )-4-(hydroxyimino)-2-phenylnaphtho [2,1- d ]oxazol-5(4 H )-one and 2-phenyl-1-hydroxy-1 H -naphtho[2,3- d ]imidazole-4,9-dione. In addition, 2-phenylnaphtho[2,1- d ]oxazol-4,5-dione and N -(3-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide are also formed. The reaction of 2-benzylamino-3-chloro-1,4-naphthoquinone with nitrosylsulfuric acid in acetic acid gives 3-diazonapthalene-1,2,4(3 H )-trione and benzaldehyde.