Formation of 1,1,4,4-tetramethoxy-2,3,5,6-tetrahydroximinocyclohexane by the interaction of trinitrosophloroglucinol with hydroxylamine hydrochloride in methanol

Authors

  • В. А. Самсонов Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • Л. Б. Володарский Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • Г. Х. Хисамутдинов Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090

Abstract

1,1,4,4-Tetramethoxy-2,3,5,6-tetrahydroximinocyclohexane was obtained by the treatment of trinitrosoploroglucinol with hydroxylamine hydrochloride in methanol. Oxidation of the product with an alkaline solution of potassium hexacyanoferrrate(III) gave a mixture of the isomers 4,4,8,8-tetramethoxy-4H, 8H-benzo[1,2-c:4,5-c']bis[1.2.5]oxadiazole-1,7-dioxide.and 4,4,8,8-tetramethoxy-4H, 8H-benzo[1,2-c:4,5-c']bis-[1.2.5]oxadiazole-1,7-dioxide. Removal of the N-oxide groups from these compounds with triethyl phosphite followed by hydrolysis of the diketal groups gave 4,8-dioxo-4H, 8H-benzo[1,2-c:4,5-c']bis[1.2.5]-dioxazole. Reaction with malonodinitrile gave 4,8-di(dicyanomethylene)-4H, 8H-benzo[1,2-c:4,5-c']bis[1.2.5]-oxadiazole which is an analog of known electron acceptors.

How to Cite
Samsonov, V. A.; Volodarskii, L. V.; Khisamutdinov, G. K. Chem. Heterocycl. Compd. 1997, 33, 471. [Khim. Geterotsikl. Soedin. 1997, 549.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02321395

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Published

2025-10-22

Issue

No. 4 (1997)

Section

Original Papers