New Nitrogen-Containing Five-Membered Heterocyclic ortho-Dicarbonitriles for Preparation of Macroheterocycles

Zh. V. Chirkova,^@ M. V. Kabanova, V. S. Sharunov, A. S. Danilova, I. G. Abramov, S. I. Filimonov, D. V. Luferenko, and M. E. Soloviev

Dedicated to the Corresponding Member of the Russian Academy of Sciences, professor Koifman O.I. on the occasion of his 70th birthday

Yaroslavl State Technical University, 150023 Yaroslavl, Russia

^@Corresponding author E-mail: chirkovazhv@ystu.ru

DOI: 10.6060/mhc140378c

Macroheterocycles 2014 7(3) 296-301

The reaction of aromatic nucleophilic substitution in 4-methyl-5-nitrophthalonitrile with reagents different structures was used for the synthesis of new substituted 4-azidophthalonitriles. The interaction of the obtained 4-azidophthalonitriles with acetylacetone leads to the formation of substituted (1,2,3-triazol-1-yl)-5-styrylphthalonitriles; the refluxing of 4-azidophthalonitriles in ethyleneglycol results in formation of 2-aryl-1H-indole-5,6-dicarbonitriles. The obtained nitrogen-containing heterocyclic ortho-dicarbonitriles can be used for preparation of macroheterocycles. The structure of all products was established by the data of IR, NMR spectroscopy (including two-dimensional correlation NOESY- spectroscopy) and mass-spectrometry.

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New Nitrogen-Containing Five-Membered Heterocyclic ortho-Dicarbonitriles for Preparation of Macroheterocycles

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