The synthesis of tetrakisdehydrotetraazaannulenes. Tetramethyl(36)-, -(48)annulene, and their benzoannelated derivatives.

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概要

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• The conjugated mono-, di-, tri-, and tetraene, containing a terminal acetylene group were converted into a variety of symmetrical and unsymmetrical conjugated azines on treatment with aqueous hydrazine in ethanol. Oxidative couplings of these azines were attempted using anhydrous copper(II) acetate in pyridine and ether. Each of unsymmetrical azines, 3,16-dimethyl-8,9-diaza-3,5,7,9,11,13,15-octadecaheptaene-1,17-diyne and 1,10-bis(<I>o</I>-ethynylphenyl)-4,5-diaza-1,3,5,7,9-decapentaene, gave the corresponding two isomeric cyclic dimers: The former gave 7,12,25,30-tetramethyl-8,10,26,28-tetrakisdehydro-1,2,17,18-tetraaza[36]annulene and 7,12,25,30-tetramethyl-8,10,26,28-tetrakisdehydro-1,2,19,20-tetraaza[36]annulene, and the latter gave 6,7:12,13:24,25:30,31-tetrabenzo-8,10,26,28-tetrakisdehydro-1,2,17,18-tetraaza[36]annulene and 6,7:12,13:24,25:30,31-tetrabenzo-8,10,26,28-tetrakisdehydro-1,2,19,20-tetraaza[36]annulene, although only in poor yields. Coupling of symmetrical azines, 3,22-dimethyl-12,13-diaza-3,5,7,9,11,13,15,17,19,21-tetraeicosadecaene-1,23-diyne and 1,16-bis(<I>o</I>-ethynylphenyl)-8,9-diaza-1,3,5,7,9,11,13,15-hexadecaoctaene, furnished cyclic dimers, 11,16,35,40-tetramethyl-12,14,36,38-tetrakisdehydro-1,2,25,26-tetraaza[48]annulene and 10,11:16,17:34,35:40,41-tetrabenzo-12,14,36,38-tetrakisdehydro-1,2,25,26-tetraaza[48]annulene, respectively, in moderate yields. Examination of <SUP>1</SUP>H NMR spectra indicates that these tetraazaannulenes are atropic.

• 公益社団法人 日本化学会の論文

著者

• Nakada Tetsuya

  Department of Chemistry, Faculty of Science, Toyama University

• Kirita Mitsuru

  Department of Chemistry, Faculty of Science, Toyama University

• Murosawa Yoshiko

  Department of Chemistry, Faculty of Science, Toyama University

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