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Synthesis of oxygen and nitrogen heterocyclic rings from bromonitroalkenes and cyclic β-diketones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Condensingα-alkyl(aryl)-β-bromo-β-nitroethylenes with dimedon and dihydroresorcinol gives a number of derivatives of nitrohexahydrobenzofuran, reduced using Raney nickel catalyst, to substituted hexahydroindolones, boiling with the same catalyst in ethanol giving tetrahydroindolones. Acid hydrolysis of derivatives of nitrohexahydrobenzofuran gives monocarboxylic acids (only the furan ring being opened), or dicarboxylic keto-acids (both rings opened). Reaction of nitrohexahydrobenzofurans with p-nitrophenylhydrazine gives monohydrazones. 2-Nitro-3-(m-nitrophenyl)hexahydrobenzofurans, when boiled with excess triethylamine, lose nitrous acid to give 3-(m-nitrophenyl)tetrahydrobenzofurans.

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Authors and Affiliations

  1. Gertsen Leningrad State Teachers' Training College, USSR

    V. M. Berestovitskaya, A. S. Sopova & V. V. Perekalin

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  1. V. M. Berestovitskaya
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  2. A. S. Sopova
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  3. V. V. Perekalin
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Berestovitskaya, V.M., Sopova, A.S. & Perekalin, V.V. Synthesis of oxygen and nitrogen heterocyclic rings from bromonitroalkenes and cyclic β-diketones. Chem Heterocycl Compd 3, 313–317 (1967). https://doi.org/10.1007/BF00945352

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